ZIZANOIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H22O2
Molecular Weight	234.334
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)[C@@H]2CC[C@]3(C2)[C@H](CC[C@@H]3C1=C)C(O)=O

InChI

InChIKey=IJGMVUXEZUEDJR-RTWAVKEYSA-N

InChI=1S/C15H22O2/c1-9-11-4-5-12(13(16)17)15(11)7-6-10(8-15)14(9,2)3/h10-12H,1,4-8H2,2-3H3,(H,16,17)/t10-,11-,12-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C15H22O2
Molecular Weight	234.334
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23841574

Zizanoic acid is a sesquiterpene in vetiver oil. Zizanoic acid exhibited significant antimycobacterial activity against drug-resistant mutants of M. smegmatis and virulent strain H37Rv of M. tuberculosis. These observations may be of great help in the QSAR-based antimycobacterial drug designing from a very common, inexpensive and non-toxic natural product for the management of MDR and XDR tuberculosis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mycobacterium smegmatis 3 Target ID: CHEMBL613088 Sources: Mycobacterium tuberculosis	Inhibitor 8504
Mycobacterium tuberculosis H37Rv 11 Target ID: CHEMBL2111188 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23841574	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Mycobacterium smegmatis infection 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23841574	Curative		Basic research	Unknown Approved Use Unknown
Tuberculosis 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23841574	Curative		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tricyclic sesquiterpenes from Vetiveria zizanoides (L.) Nash as antimycobacterial agents.	2013-11	23841574
Valorization of Brazilian vetiver (Vetiveria zizanioides (L.) Nash ex Small) oil.	2004-10-20	15479026

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Zizanoic acid inhibited Mycobacterium smegmatis with MIC 12.5 ug/ml

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:36:34 GMT 2025` Edited by `admin` on `Mon Mar 31 22:36:34 GMT 2025`
Record UNII	6W12127I74
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZIZANOIC ACID

Common Name

English

J14.140B

Preferred Name

English

7,7-DIMETHYL-6-METHYLENETRICYCLO(6.2.1.0(SUP 1,5))UNDECANE-2-CARBOXYLIC ACID

Systematic Name

English

VETIVENIC ACID

Common Name

English

(3S)-2,3,4,5,6,7,8,8A.ALPHA.-OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-1H-3A.ALPHA.,6.ALPHA.-METHANOAZULENE-3.ALPHA.-CARBOXYLIC ACID

Systematic Name

English

(3S-(3ALPHA,3AALPHA,6ALPHA,8AALPHA))-OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-1H-3A,6-METHANOAZULENE-3-CARBOXYLIC ACID

Systematic Name

English

1H-3A,6-METHANOAZULENE-3-CARBOXYLIC ACID, OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-, (3S-(3.ALPHA.,3A.ALPHA.,6.ALPHA.,8A.ALPHA.))-

Systematic Name

English

KHUSENIC ACID

Common Name

English

1H-3A.ALPHA.,6-METHANOAZULENE-3-CARBOXYLIC ACID, 2,3.BETA.,4,5,6.BETA.,7,8,8A.ALPHA.-OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-

Systematic Name

English

(+)-ZIZANOIC ACID

Common Name

English

(3S,3AR,6R,8AS)-7,7-DIMETHYL-8-METHYLENEOCTAHYDRO-1H-3A,6-METHANOAZULENE-3-CARBOXYLIC ACID

Systematic Name

English

1H-3A,6-METHANOAZULENE-3-CARBOXYLIC ACID, OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-, (3S,3AR,6R,8AS)-

Systematic Name

English

7,7-DIMETHYL-8-METHYLIDENEOCTAHYDRO-1H-3A,6-METHANOAZULENE-3-CARBOXYLIC ACID

Common Name

English

1H-3A,6-METHANOAZULENE-3-CARBOXYLIC ACID, OCTAHYDRO-7,7-DIMETHYL-8-METHYLENE-

Common Name

English

Code System Code Type Description

PUBCHEM

21764437