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Adenosine cyclic phosphate

PubChem CID
6076
Structure
Adenosine cyclic phosphate_small.png
Adenosine cyclic phosphate_3D_Structure.png
Molecular Formula
Synonyms
  • Cyclic AMP
  • cAMP
  • 60-92-4
  • Adenosine 3',5'-cyclic monophosphate
  • 3',5'-cyclic AMP
Molecular Weight
329.21 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-08
  • Modify:
    2025-01-18
Description
3',5'-cyclic AMP is a 3',5'-cyclic purine nucleotide having having adenine as the nucleobase. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an adenyl ribonucleotide and a 3',5'-cyclic purine nucleotide. It is a conjugate acid of a 3',5'-cyclic AMP(1-).
Cyclic adenosine monophosphate (cAMP, cyclic AMP or 3'-5'-cyclic adenosine monophosphate) is a molecule that is important in many biological processes; it is derived from adenosine triphosphate (ATP).
Cyclic AMP is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
See also: Jujube fruit (part of) ... View More ...

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Adenosine cyclic phosphate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

IVOMOUWHDPKRLL-KQYNXXCUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H12N5O6P
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

60-92-4

2.3.3 Deprecated CAS

11002-78-1

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 ChEBI ID

2.3.7 ChEMBL ID

2.3.8 DrugBank ID

2.3.9 DSSTox Substance ID

2.3.10 HMDB ID

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 PharmGKB ID

2.3.16 Pharos Ligand ID

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3',5'-Monophosphate, Adenosine Cyclic
  • Adenosine Cyclic 3',5' Monophosphate
  • Adenosine Cyclic 3',5'-Monophosphate
  • Adenosine Cyclic 3,5 Monophosphate
  • Adenosine Cyclic Monophosphate
  • Adenosine Cyclic-3',5'-Monophosphate
  • AMP, Cyclic
  • Cyclic 3',5'-Monophosphate, Adenosine
  • Cyclic AMP
  • Cyclic AMP, (R)-Isomer
  • Cyclic AMP, Disodium Salt
  • Cyclic AMP, Monoammonium Salt
  • Cyclic AMP, Monopotassium Salt
  • Cyclic AMP, Monosodium Salt
  • Cyclic AMP, Sodium Salt
  • Cyclic Monophosphate, Adenosine
  • Cyclic-3',5'-Monophosphate, Adenosine
  • Monophosphate, Adenosine Cyclic

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
329.21 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-2.6
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
329.05252012 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
329.05252012 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
155 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
498
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

219-220 °C
PhysProp
219 - 220 °C

3.2.3 Solubility

4 mg/mL

3.2.4 LogP

-2.96
HANSCH,C ET AL. (1995)
-2.96
HANSCH,C ET AL. (1995)

3.2.5 Collision Cross Section

176.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
172 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
175.07 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

176.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

172.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

188.6 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

181 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

188.8 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

171.8 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

172 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

172.6 Ų [M+H]+

172.7 Ų [M+H]+

189 Ų [M+Na]+

177 Ų [M+H]+

171.9 Ų [M-H]-

181.3 Ų [M+Na]+

182.3 Ų [M+Na]+

S50 | CCSCOMPEND | The Unified Collision Cross Section (CCS) Compendium | DOI:10.5281/zenodo.2658162

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.3.2 Cosmetics

Skin conditioning
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 4
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Spectra ID
Instrument Type
Varian
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
4.34:25.13, 4.35:16.42, 8.22:100.00, 4.55:5.99, 4.37:4.42, 4.31:2.78, 4.34:17.53, 4.51:5.98, 8.22:95.97, 4.33:37.69, 4.52:5.99, 4.55:5.95, 6.16:65.45, 4.31:2.88
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Spectra ID
Instrument Type
Bruker
Solvent
D2O
pH
7.4
Shifts [ppm]:Intensity
6.11:3.14, 4.54:0.75, 4.34:2.31, 4.72:2.78, 4.58:0.73, 8.14:3.49, 4.52:0.73, 4.59:0.70, 4.75:1.19, 8.17:3.39, 4.36:2.94
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4.1.2 13C NMR Spectra

1 of 3
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Spectra ID
Instrument Type
Bruker
Solvent
D2O
pH
7.4
Shifts [ppm]:Intensity
74.96:47.66, 94.22:97.37, 121.22:21.86, 74.48:46.89, 70.02:32.58, 158.05:28.95, 150.78:28.76, 75.04:47.38, 79.99:47.96, 155.54:70.98, 74.52:45.52, 80.04:48.51, 70.10:36.71, 142.37:69.48
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Copyright
Database Compilation Copyright © 2021-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.3 31P NMR Spectra

1 of 2
Instrument Name
Bruker HX-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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2 of 2
Instrument Name
Bruker HX-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 2D NMR Spectra

4.2.1 1H-1H NMR Spectra

2D NMR Spectra Type
1H-1H TOCSY
Spectra ID
Shifts [ppm] (F2:F1)
4.63:4.83, 4.53:4.33, 4.35:4.59, 6.72:4.82, 4.83:4.83, 4.35:4.32, 4.58:4.76, 4.35:4.54, 4.74:4.75, 4.73:4.83, 4.54:4.75, 4.35:4.50, 4.73:4.36, 4.58:4.36, 8.18:8.17, 4.22:4.83, 4.54:4.36, 4.35:4.35, 8.15:8.14, 6.12:6.12, 4.58:4.73, 4.56:4.83, 4.54:4.73, 4.49:4.83, 4.35:4.39, 4.45:4.83, 4.67:4.83, 4.35:4.36, 4.73:4.39, 4.35:4.73, 4.53:4.53, 4.74:4.59, 4.32:4.83, 6.69:4.83, 4.58:4.58, 4.59:4.39, 4.74:4.73, 4.54:4.35, 6.21:6.11, 4.73:4.33, 4.73:6.12, 4.77:4.83, 4.73:4.50, 4.73:4.53
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4.2.2 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
8.19:142.35:0.74, 4.53:69.95:0.26, 6.13:94.26:1.00, 8.17:155.44:0.51, 4.34:69.95:0.46, 4.75:79.88:0.30, 4.35:74.37:0.51, 4.56:69.95:0.24, 4.73:75.01:0.67
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 8
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Spectra ID
Instrument Type
GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
Ionization Mode
Positive
Top 5 Peaks

73.0 1

236.0 0.33

192.0 0.20

208.0 0.17

211.0 0.16

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Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

73.0 100

236.0 33.13

192.0 19.52

208.0 16.72

211.0 16.02

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Notes
instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies

4.3.2 MS-MS

1 of 8
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

330.0603 100

136.0648 33.32

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2 of 8
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

136.06352 100

330.05569 63.45

312.05301 8.82

119.03478 3.62

176.99254 2.71

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4.3.3 LC-MS

1 of 22
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Authors
Takahashi H, Kanaya S, Ogasawara N, Graduate School of Information Science, NAIST
Instrument
LTQ Orbitrap XL, Thermo Scientfic
Instrument Type
LC-ESI-ITFT
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
35eV
Column Name
TOSOH TSKgel ODS-100V 5um Part no. 21456
Retention Time
9.749348 min
Top 5 Peaks

330.0599 999

284.099482 163

331.062281 116

659.11108 71

171.149125 39

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License
CC BY-SA
2 of 22
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Authors
Takahashi H, Kanaya S, Ogasawara N, Graduate School of Information Science, NAIST
Instrument
LTQ Orbitrap XL, Thermo Scientfic
Instrument Type
LC-ESI-ITFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
35eV
Column Name
TOSOH TSKgel ODS-100V 5um Part no. 21456
Retention Time
9.760177 min
Precursor m/z
284.1
Top 5 Peaks

152.028412 999

134.07843 3

135.162689 2

212.187042 1

211.30896 1

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License
CC BY-SA

4.3.4 Other MS

1 of 3
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MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
328.25
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
negative
Collision Energy
60
Top 5 Peaks

134 100

133 17.68

79 11.19

78 3.24

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MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
328.25
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
negative
Collision Energy
50
Top 5 Peaks

134 100

133 17.24

79 12.63

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4.4 IR Spectra

4.4.1 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Calbiochem, EMD Chemicals, Inc., an Affiliate of Merck KGaA, Darmstadt, Germany
Catalog Number
116801
Lot Number
802158
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
851205
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 FDA National Drug Code Directory

7.2 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Human Metabolite Information

9.1.1 Tissue Locations

  • All Tissues
  • Placenta

9.1.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Golgi apparatus

9.1.3 Metabolite Pathways

9.2 Biochemical Reactions

10 Use and Manufacturing

10.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125

10.1.1 Use Classification

Cosmetics -> Skin conditioning
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

10.1.2 Household Products

Household & Commercial/Institutional Products

Information on 1 consumer products that contain cyclic AMP (adenosine cyclic phosphate) in the following categories is provided:

• Personal Care

10.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Adenosine, cyclic 3',5'-(hydrogen phosphate): ACTIVE

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

Note
Pictograms displayed are for 66.7% (4 of 6) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 33.3% (2 of 6) of reports.
Pictogram(s)
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H314 (16.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (16.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 6 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 2 of 6 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 2 notifications provided by 4 of 6 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Skin Corr. 1B (16.7%)

Skin Irrit. 2 (50%)

Eye Dam. 1 (16.7%)

Eye Irrit. 2 (50%)

11.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Adenosine, cyclic 3',5'-(hydrogen phosphate)
New Zealand EPA Inventory of Chemical Status
Adenosine, cyclic 3',5'-(hydrogen phosphate): Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

11.3 Other Safety Information

Chemical Assessment
IMAP assessments - Adenosine, cyclic 3',5'-(hydrogen phosphate): Environment tier I assessment

12 Associated Disorders and Diseases

Disease
Headache
References
PubMed: 15196297
Disease
Idiopathic polyneuritis
References
PubMed: 6326460
Disease
Hypoxic-ischemic encephalopathy
References
Disease
Chronic renal failure
References

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Nature Journal References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

15.3 Drug-Drug Interactions

15.4 Pathways

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
Zebrafish Pathway Metabolite MetFrag Local CSV (Beta) | DOI:10.5281/zenodo.3457553
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 KEGG: Metabolite

18.5 ChemIDplus

18.6 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

18.7 ChEMBL Target Tree

18.8 UN GHS Classification

18.9 EPA CPDat Classification

18.10 NORMAN Suspect List Exchange Classification

18.11 CCSBase Classification

18.12 EPA DSSTox Classification

18.13 Consumer Product Information Database Classification

18.14 EPA TSCA and CDR Classification

18.15 LOTUS Tree

18.16 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Adenosine, cyclic 3',5'-(hydrogen phosphate)
    https://services.industrialchemicals.gov.au/search-assessments/
    Adenosine, cyclic 3',5'-(hydrogen phosphate)
    https://services.industrialchemicals.gov.au/search-inventory/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
    Cyclic adenosine monophosphate
    https://www.drugbank.ca/drugs/DB02527
  5. EPA Chemicals under the TSCA
    Adenosine, cyclic 3',5'-(hydrogen phosphate)
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  8. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  9. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  10. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  11. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  12. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Cyclic amp
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  13. ChEBI
  14. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  15. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  16. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  17. Yeast Metabolome Database (YMDB)
    LICENSE
    YMDB is offered to the public as a freely available resource.
    http://www.ymdb.ca/downloads
  18. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  19. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  20. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
    CYCLIC ADENOSINE MONOPHOSPHATE
    https://www.dgidb.org/drugs/drugbank:DB02527
  21. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  22. Therapeutic Target Database (TTD)
  23. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  24. ECI Group, LCSB, University of Luxembourg
    LICENSE
    Data: CC-BY 4.0; Code: Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    3',5'-cyclic AMP
  25. Natural Product Activity and Species Source (NPASS)
  26. EPA Chemical and Products Database (CPDat)
  27. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  28. MassBank Europe
  29. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  30. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Adenosine 3',5'-cyclic monophosphate
    http://www.nist.gov/srd/nist1a.cfm
  31. SpectraBase
    Adenosine 3',5'-cyclic monophosphate
    https://spectrabase.com/spectrum/AV7GXYbqYFL
    Adenosine 3',5'-cyclic monophosphate
    https://spectrabase.com/spectrum/8piiF8by8Vb
    Adenosine-3',5'-cyclic phosphate
    https://spectrabase.com/spectrum/9rUAsMXqP5e
    Adenosine 3',5'-cyclic monophosphate
    https://spectrabase.com/spectrum/HTFkE5DNwfi
    ADENOSINE-3',5'-CYCLOPHOSPHATE
    https://spectrabase.com/spectrum/C05XsNZFoa
    ADENOSINE-3',5'-CYCLOPHOSPHATE
    https://spectrabase.com/spectrum/AyEYx4h2vU4
  32. Japan Chemical Substance Dictionary (Nikkaji)
  33. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  34. MarkerDB
    LICENSE
    This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
    https://markerdb.ca/
  35. Metabolomics Workbench
  36. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  37. Nature Chemical Biology
  38. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
    cyclic adenosine monophosphate
    https://www.pharmgkb.org/chemical/PA166178640
  39. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  40. Protein Data Bank in Europe (PDBe)
  41. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  42. Springer Nature
  43. Wikidata
    adenosine cyclic phosphate
    https://www.wikidata.org/wiki/Q210041
  44. Wikipedia
  45. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  46. PubChem
  47. GHS Classification (UNECE)
  48. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  49. PATENTSCOPE (WIPO)
CONTENTS