An official website of the United States government

17-Hydroxyyohimban-16-carboxylic acid

PubChem CID
630921
Structure
17-Hydroxyyohimban-16-carboxylic acid_small.png
17-Hydroxyyohimban-16-carboxylic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 17-Hydroxyyohimban-16-carboxylic acid
  • Oprea1_780636
  • SCHEMBL1691213
  • Yohimban-16-carboxylic acid, 17-hydroxy-, (16.alpha.,17.alpha.)-
  • DTXSID00859454
Molecular Weight
340.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-03-28
  • Modify:
    2025-01-18
See also: Yohimbic Acid (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
17-Hydroxyyohimban-16-carboxylic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C20H24N2O3/c23-17-6-5-11-10-22-8-7-13-12-3-1-2-4-15(12)21-19(13)16(22)9-14(11)18(17)20(24)25/h1-4,11,14,16-18,21,23H,5-10H2,(H,24,25)
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

AADVZSXPNRLYLV-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C1CC(C(C2C1CN3CCC4=C(C3C2)NC5=CC=CC=C45)C(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H24N2O3
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 DSSTox Substance ID

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
340.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3
Property Value
0.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
340.17869263 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
340.17869263 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
76.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
25
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
541
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
5
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 2019.01.04)

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

NIST Number
238573
Library
Main library
Total Peaks
307
m/z Top Peak
339
m/z 2nd Highest
340
m/z 3rd Highest
169
Thumbnail
Thumbnail

4.1.2 LC-MS

1 of 39
View All
Authors
Tetsuya Mori, Center for Sustainable Resource Science, RIKEN
Instrument
LC, Waters Acquity UPLC System; MS, Waters Xevo G2 Q-Tof
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
6V
Column Name
Acquity bridged ethyl hybrid C18 (1.7 um, 2.1 mm * 100 mm, Waters)
Retention Time
3.8201
Precursor m/z
341.1859691
Precursor Adduct
[M+H]+
Top 5 Peaks

341.1857 999

144.08035 534

198.11302 151

145.08478 60

210.11324 32

Thumbnail
Thumbnail
License
CC BY-NC-SA
Reference
Tsugawa H., Nakabayashi R., Mori T., Yamada Y., Takahashi M., Rai A., Sugiyama R., Yamamoto H., Nakaya T., Yamazaki M., Kooke R., Bac-Molenaar JA., Oztolan-Erol N., Keurentjes JJB., Arita M., Saito K. (2019) "A cheminformatics approach to characterize metabolomes in stable-isotope-labeled organisms" Nature Methods 16(4):295-298. [doi:10.1038/s41592-019-0358-2]
2 of 39
View All
Authors
Tetsuya Mori, Center for Sustainable Resource Science, RIKEN
Instrument
LC, Waters Acquity UPLC System; MS, Waters Xevo G2 Q-Tof
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
6V
Column Name
Acquity bridged ethyl hybrid C18 (1.7 um, 2.1 mm * 100 mm, Waters)
Retention Time
3.8201
Precursor m/z
341.1859691
Precursor Adduct
[M+H]+
Top 5 Peaks

341.18689 999

341.23959 32

198.11275 11

144.08057 8

Thumbnail
Thumbnail
License
CC BY-NC-SA
Reference
Tsugawa H., Nakabayashi R., Mori T., Yamada Y., Takahashi M., Rai A., Sugiyama R., Yamamoto H., Nakaya T., Yamazaki M., Kooke R., Bac-Molenaar JA., Oztolan-Erol N., Keurentjes JJB., Arita M., Saito K. (2019) "A cheminformatics approach to characterize metabolomes in stable-isotope-labeled organisms" Nature Methods 16(4):295-298. [doi:10.1038/s41592-019-0358-2]

6 Chemical Vendors

7 Literature

7.1 Consolidated References

8 Patents

8.1 Depositor-Supplied Patent Identifiers

9 Biological Test Results

9.1 BioAssay Results

10 Classification

10.1 EPA DSSTox Classification

11 Information Sources

CONTENTS