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Hydroxyproline

PubChem CID
5810
Structure
Hydroxyproline_small.png
Hydroxyproline_3D_Structure.png
Molecular Formula
Synonyms
  • L-Hydroxyproline
  • 51-35-4
  • trans-4-Hydroxy-L-proline
  • hydroxyproline
  • (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid
Molecular Weight
131.13 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-04
Description
Trans-4-hydroxy-L-proline is an optically active form of 4-hydroxyproline having L-trans-configuration. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is a tautomer of a trans-4-hydroxy-L-proline zwitterion.
Hydroxyproline is a neutral heterocyclic protein amino acid. It is found in collagen and as such it is common in many gelatin products. Hydroxyproline is mostly used as a diagnostic marker of bone turnover and liver fibrosis. Therapeutically, hydroxyproline is being studied as an an experimental medicine but is approved in France as a combination topical gel product called Cicactive for small, superficial wounds.
Hydroxyproline is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Hydroxyproline.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-Hyp-OH
Sequence
X
HELM
PEPTIDE1{[Hyp]}$$$$
IUPAC
(4R)-4-hydroxy-L-proline

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

PMMYEEVYMWASQN-DMTCNVIQSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

C1[C@H](CN[C@@H]1C(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C5H9NO3
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

51-35-4

3.3.3 Deprecated CAS

138-46-5, 17210-41-2, 21105-75-9, 24784-87-0, 54733-36-7

3.3.4 European Community (EC) Number

3.3.5 UNII

3.3.6 ChEBI ID

3.3.7 ChEMBL ID

3.3.8 DrugBank ID

3.3.9 DSSTox Substance ID

3.3.10 HMDB ID

3.3.11 KEGG ID

3.3.12 Metabolomics Workbench ID

3.3.13 NCI Thesaurus Code

3.3.14 Nikkaji Number

3.3.15 NSC Number

3.3.16 RXCUI

3.3.17 Wikidata

3.3.18 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • N-methyl-trans-4-hydroxy-L-proline
  • NMH-Pro
  • trans-4-hydroxy-L-proline

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
131.13 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-3.3
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
4
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
131.058243149 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
131.058243149 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
69.6Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
9
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
125
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
2
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)

4.2 Experimental Properties

4.2.1 Physical Description

Solid; [Merck Index] White crystalline powder; [Alfa Aesar MSDS]
Solid

4.2.2 Boiling Point

Decomposes
From MSDS.

4.2.3 Melting Point

274°C
From The Merck Index monographs.
274 - 275 °C

4.2.4 Solubility

Soluble in water at 0, 25, 50, and 60 °C
From The Merck Index monographs.
361 mg/mL at 25 °C

4.2.5 LogP

-3.17
HANSCH,C ET AL. (1995)

4.2.6 Dissociation Constants

pKa
pK1′ 1.82 and pK2′ 9.65
From The Merck Index monographs.

4.2.7 Collision Cross Section

130.23 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

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

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

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

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

122 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
128.1 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

127.9 Ų [M+H]+

126.7 Ų [M-H]-

139.4 Ų [M+Na]+

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

4.3 Chemical Classes

Biological Agents -> Amino Acids and Derivatives

4.3.1 Drugs

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

4.3.2 Cosmetics

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

4.3.3 Food Additives

Use unspecified -> FDA Substance added to food

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 1H NMR Spectra

1 of 5
View All
Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
3.37:66.35, 3.46:83.59, 3.37:100.00, 2.16:45.84, 2.13:38.33, 3.49:54.15, 3.46:79.77, 2.15:40.74, 2.40:47.80, 2.43:20.01, 3.37:91.42, 3.37:73.51, 3.34:55.84, 2.44:39.83, 2.43:39.27, 4.33:35.56, 4.35:30.58, 3.48:48.61, 2.40:29.10, 2.12:36.18, 4.34:30.56, 2.42:30.38, 2.41:48.74, 2.42:32.39, 2.12:35.80, 2.41:31.79, 3.34:62.53, 3.34:61.88, 3.35:36.68, 2.17:43.84, 2.17:45.05, 2.44:28.82, 2.14:35.83, 2.15:75.15, 2.39:31.19, 2.14:35.37, 2.45:20.91, 4.32:29.70
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Spectra ID
Frequency
500 MHz
Solvent
H2O
Shifts [ppm]
3.46, 4.33, 2.42, 2.14, 4.67, 3.36
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5.1.2 13C NMR Spectra

1 of 4
View All
Spectra ID
Instrument Type
Bruker
Frequency
125 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
72.80:58.28, 176.93:17.85, -0.00:5.11, 40.12:60.23, 55.75:53.75, 62.62:47.87
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Spectra ID
Frequency
400 MHz
Solvent
H2O
Shifts [ppm]
176.93, 40.12, 72.80, 55.75, 62.62
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5.2 2D NMR Spectra

5.2.1 1H-1H NMR Spectra

2D NMR Spectra Type
1H-1H TOCSY
Spectra ID
Shifts [ppm] (F2:F1)
2.42:2.40, 2.15:4.34, 4.67:4.66, 3.47:3.35, 2.15:3.46, 3.37:2.40, 2.15:2.40, 2.42:4.36, 2.42:2.12, 3.55:3.33, 2.15:3.37, 2.42:3.49, 4.67:4.36, 2.15:2.15, 4.34:4.36, 2.42:4.66, 3.48:2.42, 2.15:4.31, 3.36:3.34, 3.47:2.45, 4.67:2.46, 2.42:4.34, 4.67:3.46, 3.36:3.46, 2.42:3.46, 3.36:2.18, 4.34:4.31, 4.67:3.37, 3.36:2.12, 4.67:3.49, 3.36:3.37, 2.15:2.45, 3.48:2.18, 3.48:2.40, 2.15:4.66, 2.15:4.36, 3.36:4.34, 3.36:2.15, 4.67:2.42, 4.34:4.66, 3.48:3.46, 3.59:3.33, 2.42:2.42, 2.42:4.31, 2.15:2.12, 3.47:3.37, 3.47:4.66, 2.15:2.18, 4.34:4.34, 4.67:2.19, 4.67:2.40, 2.15:3.49, 3.48:3.49, 3.37:2.42, 2.00:4.80, 4.67:4.34, 4.67:3.34, 4.67:4.32, 3.48:2.12, 2.42:3.37, 4.67:2.15, 2.42:3.34, 2.42:2.45, 3.47:4.34, 3.47:2.15, 3.37:4.66, 2.42:2.18, 2.15:3.34, 2.15:2.42, 2.42:2.15
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5.2.2 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
4.33:62.59:1.00, 3.48:55.86:0.59, 2.44:40.24:0.51, 3.36:55.86:0.57, 4.67:72.82:0.40, 2.15:40.24:0.63
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5.3 Mass Spectrometry

5.3.1 GC-MS

1 of 11
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Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

158.0 1

159.0 0.19

103.0 0.16

142.0 0.13

116.0 0.12

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

230.1 100

140.1 41.74

231.1 19.56

232.1 8.52

147.1 7.99

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Notes
instrument=GCMS-2010 Plus, Shimadzu

5.3.2 MS-MS

1 of 6
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Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

86.049 100

131.917 99.51

68.114 17.65

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad
2 of 6
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Spectra ID
Instrument Type
Quattro_QQQ
Ionization Mode
Positive
Top 5 Peaks

68.114 100

86.026 65.77

41.323 27.08

58.179 18.68

131.839 4.15

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Notes
delivery=Flow_Injectionanalyzer=Triple_Quad

5.3.3 LC-MS

1 of 9
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6530 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Retention Time
0.215 min
Precursor m/z
132.0655
Precursor Adduct
[M+H]+
Top 5 Peaks

86.0606 999

68.0505 612

132.0654 434

41.0395 111

114.054 18

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License
CC BY
2 of 9
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6530 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Retention Time
0.220 min
Precursor m/z
132.0655
Precursor Adduct
[M+H]+
Top 5 Peaks

68.0504 999

86.0606 656

58.0663 192

132.0672 31

67.0389 2

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License
CC BY

5.3.4 Other MS

1 of 4
View All
Authors
Miyagawa H, Akimoto S, Yamasaki K, GL Sciences Inc.
Instrument
GCMS-2010 Plus, Shimadzu
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Column Name
InertCap 5MS/NP 0.25 mmI.D. x 30 m, df=0.25 um
Retention Time
601.47
Top 5 Peaks

230.1 999

140.1 417

231.1 195

232.1 85

147.1 80

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License
CC BY-SA
2 of 4
View All
MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
130.09
Instrument
TQD, Waters
Instrument Type
Flow-injection QqQ/MS
Ionization
ESI
Ionization Mode
negative
Collision Energy
10
Top 5 Peaks

130 100

129 13.57

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5.4 IR Spectra

5.4.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Catalog Number
H5440
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company LLC
Catalog Number
H-6002
Lot Number
85H0133
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Spectrochem Pvt. Ltd.
Catalog Number
10829
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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5.5 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Spectrochem Pvt. Ltd., India
Catalog Number
10829
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
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7 Chemical Vendors

8 Drug and Medication Information

8.1 Drug Indication

Used in France as a combination product for the treatment of small, superficial wounds.

8.2 Drug Labels

Drug and label
Active ingredient and drug

8.3 Biomarker Information

9 Food Additives and Ingredients

9.1 FDA Substances Added to Food

Used for (Technical Effect)
Use unspecified

10 Pharmacology and Biochemistry

10.1 Pharmacodynamics

Hydroxyproline as well as proline and glycine are the major components of collagen. Collagen is on one of the main building blocks of connective tissue such as skin, bone, and cartilage. Thus when these tissues are damaged, hydroxyproline is necessary for repair of the damaged area.

10.2 Human Metabolite Information

10.2.1 Tissue Locations

  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen

10.2.2 Cellular Locations

  • Endoplasmic reticulum
  • Mitochondria

10.2.3 Metabolite Pathways

10.3 Biochemical Reactions

11 Use and Manufacturing

11.1 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
Sources/Uses
An analog of proline and an non-essential amino acid found in collagen; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

11.1.1 Use Classification

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

11.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
L-Proline, 4-hydroxy-, (4R)-: ACTIVE

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 88.9% (24 of 27) of all reports. Pictograms displayed are for 11.1% (3 of 27) of reports that indicate hazard statements.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (11.1%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (11.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (11.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, 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 27 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 24 of 27 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 3 notifications provided by 3 of 27 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.

12.1.2 Hazard Classes and Categories

Skin Irrit. 2 (11.1%)

Eye Irrit. 2A (11.1%)

STOT SE 3 (11.1%)

12.1.3 Hazards Summary

May cause irritation; [Alfa Aesar MSDS] See L-Proline.

12.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: L-Proline, 4-hydroxy-, (4R)-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
L-Proline, 4-hydroxy-, (4R)-: Does not have an individual approval but may be used under an appropriate group standard

12.3 Other Safety Information

Chemical Assessment

IMAP assessments - L-Proline, 4-hydroxy-, trans-: Environment tier I assessment

Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health

13 Toxicity

13.1 Toxicological Information

13.1.1 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

14 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Hydroxyprolinemia
References
Disease
Attachment loss
References
PubMed: 31026179
Disease
Missing teeth
References
PubMed: 31026179
Disease
Periodontal Probing Depth
References
PubMed: 31026179
Disease
Tooth Decay
References
PubMed: 31026179
Disease
Iminoglycinuria
References

PubMed: 432003, 19033659

MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Wiley References

15.6 Chemical Co-Occurrences in Literature

15.7 Chemical-Gene Co-Occurrences in Literature

15.8 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Interactions and Pathways

17.1 Protein Bound 3D Structures

17.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Conformer

17.2 Chemical-Target Interactions

17.3 Pathways

18 Biological Test Results

18.1 BioAssay Results

19 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
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

20 Classification

20.1 MeSH Tree

20.2 NCI Thesaurus Tree

20.3 ChEBI Ontology

20.4 KEGG: Metabolite

20.5 ChemIDplus

20.6 ChEMBL Target Tree

20.7 UN GHS Classification

20.8 EPA CPDat Classification

20.9 NORMAN Suspect List Exchange Classification

20.10 CCSBase Classification

20.11 EPA DSSTox Classification

20.12 EPA TSCA and CDR Classification

20.13 LOTUS Tree

20.14 MolGenie Organic Chemistry Ontology

21 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  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/
    L-Proline, 4-hydroxy-, (4R)-, homopolymer
    https://commonchemistry.cas.org/detail?cas_rn=25249-07-4
  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
  5. DTP/NCI
    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
  6. EPA Chemicals under the TSCA
    L-Proline, 4-hydroxy-, (4R)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  7. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  8. European Chemicals Agency (ECHA)
    LICENSE
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  9. FDA Global Substance Registration System (GSRS)
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  12. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  13. NORMAN Suspect List Exchange
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    https://creativecommons.org/licenses/by/4.0/
    4-hydroxyproline
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  14. ChEBI
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  16. LOTUS - the natural products occurrence database
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  17. NCI Thesaurus (NCIt)
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    trans-4-hydroxy-L-proline
  22. Natural Product Activity and Species Source (NPASS)
    (2S,4R)-4-Hydroxypyrrolidine-2-Carboxylic Acid
    https://bidd.group/NPASS/compound.php?compoundID=NPC196359
  23. EPA Chemical and Products Database (CPDat)
  24. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
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  27. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  28. SpectraBase
  29. Japan Chemical Substance Dictionary (Nikkaji)
  30. KEGG
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    https://www.kegg.jp/kegg/legal.html
  31. MarkerDB
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    https://markerdb.ca/
  32. Metabolomics Workbench
  33. NLM RxNorm Terminology
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  34. Protein Data Bank in Europe (PDBe)
  35. RCSB Protein Data Bank (RCSB PDB)
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  38. Wikidata
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    https://www.wikidata.org/wiki/Q106345465
  39. Wikipedia
  40. Wiley
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  42. Medical Subject Headings (MeSH)
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  43. GHS Classification (UNECE)
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  45. PATENTSCOPE (WIPO)
CONTENTS