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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O3.H2O
Molecular Weight 358.4314
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of YOHIMBIC ACID MONOHYDRATE

SMILES

O.[H][C@@]12CC[C@H](O)[C@H](C(O)=O)[C@@]1([H])C[C@]3([H])N(CCC4=C3NC5=C4C=CC=C5)C2

InChI

InChIKey=UXXCUDYYOMDFPX-GPRFVYSASA-N
InChI=1S/C20H24N2O3.H2O/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);1H2/t11-,14-,16-,17-,18+;/m0./s1

HIDE SMILES / InChI
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C20H24N2O3
Molecular Weight 340.4162
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Yohimbinic acid, also known as yohimbic acid is an indole alkaloid, which was isolated from dried roots of Rauwolfia serpentina. Yohimbinic acid is a potent inhibitor of a human DNA Topoisomerase I and can inhibit cancer cells growth.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
DNA topoisomerase 1
16
Target ID: P11387|||Q9UJN0
Gene ID: 7150.0
Gene Symbol: TOP1
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 30.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Sympatholytic activity and toxicity of an amphoteric demethylated derivative of yohimbine: yohimbic acid].
1951 Oct 29
[Demonstration of the direct vasodilatory action of yohimbic acid and Py-tetrahydroquinoline].
1960 Jun 27
[EEG study of the central action of yohimbine and yohimbic acid. (Experimental research)].
1961 Aug 31
Indole alkaloids and other constituents of Rauwolfia serpentina.
2005 Jun

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Compounds 4 (yohimbinic acid) inhibited human promyelocytic leukemia (HL-60) cell growth with IC50 = 84 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:26:55 GMT 2023
Edited
by admin
on Sat Dec 16 01:26:55 GMT 2023
Record UNII
DN3BXM2IR8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
YOHIMBIC ACID MONOHYDRATE
Common Name English
YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, MONOHYDRATE, (16.ALPHA.,17.ALPHA.)-
Common Name English
Code System Code Type Description
FDA UNII
DN3BXM2IR8
Created by admin on Sat Dec 16 01:26:55 GMT 2023 , Edited by admin on Sat Dec 16 01:26:55 GMT 2023
PRIMARY
PUBCHEM
6419962
Created by admin on Sat Dec 16 01:26:55 GMT 2023 , Edited by admin on Sat Dec 16 01:26:55 GMT 2023
PRIMARY
CAS
207801-27-2
Created by admin on Sat Dec 16 01:26:55 GMT 2023 , Edited by admin on Sat Dec 16 01:26:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045578
Created by admin on Sat Dec 16 01:26:55 GMT 2023 , Edited by admin on Sat Dec 16 01:26:55 GMT 2023
PRIMARY
Related Record Type Details
Structure of YOHIMBIC ACID
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of YOHIMBIC ACID
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