YOHIMBIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H24N2O3
Molecular Weight	340.4162
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1CC[C@H]2CN3CCC4=C(NC5=C4C=CC=C5)[C@@H]3C[C@@H]2[C@H]1C(O)=O

InChI

InChIKey=AADVZSXPNRLYLV-GKMXPDSGSA-N

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)/t11-,14-,16-,17-,18+/m0/s1

HIDE SMILES / InChI

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15974606

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

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase 1 16 Target ID: P11387\|\|\|Q9UJN0 Gene ID: 7150.0 Gene Symbol: TOP1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15974606	Inhibitor 8504		30.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Indole alkaloids and other constituents of Rauwolfia serpentina.	2005-06	15974606
[EEG study of the central action of yohimbine and yohimbic acid. (Experimental research)].	1961-08-31	13862577
[Demonstration of the direct vasodilatory action of yohimbic acid and Py-tetrahydroquinoline].	1960-06-27	13854468
[Sympatholytic activity and toxicity of an amphoteric demethylated derivative of yohimbine: yohimbic acid].	1951-10-29	14896545

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 `Mon Mar 31 18:06:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:30 GMT 2025`
Record UNII	35FAV1EVEG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

YOHIMBIC ACID

Official Name

English

NSC-95096

Preferred Name

English

Yohimbic acid [WHO-DD]

Common Name

English

yohimbic acid [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29707