VERRUCARIN A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H34O9
Molecular Weight	502.5535
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1CCOC(=O)\C=C\C=CC(=O)O[C@@H]2C[C@H]3O[C@@H]4C=C(C)CC[C@]4(COC(=O)[C@H]1O)[C@]2(C)[C@]35CO5

InChI

InChIKey=NLUGUZJQJYVUHS-IDXDZYHTSA-N

InChI=1S/C27H34O9/c1-16-8-10-26-14-33-24(31)23(30)17(2)9-11-32-21(28)6-4-5-7-22(29)36-18-13-20(35-19(26)12-16)27(15-34-27)25(18,26)3/h4-7,12,17-20,23,30H,8-11,13-15H2,1-3H3/b6-4+,7-5-/t17-,18-,19-,20-,23+,25-,26-,27+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H34O9
Molecular Weight	502.5535
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27849335 | https://www.ncbi.nlm.nih.gov/pubmed/27573873 | https://www.ncbi.nlm.nih.gov/pubmed/23690045

Verrucarin A (VC-A) is a Type D macrocyclic mycotoxin which inhibits cell proliferation and induces apoptosis in cancer cells. Strong antiproliferative and apoptosis-inducing activity of verrucarin A for pancreatic ductal adenocarcinoma and prostate cancer cells through cell cycle arrest and inhibition of the prosurvival (antiapoptotic) AKT/NF-κB/mTOR signaling.has being demonstrated. Verrucarin A, a protein synthesis inhibitor, also induces growth inhibition and apoptosis in breast cancer cell lines MDA-MB-231 and T47D.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis 156 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27849335 \| https://www.ncbi.nlm.nih.gov/pubmed/23690045	Activator 1447
Protein biosynthesis 8 Target ID: Protein biosynthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/16869484	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27849335 https://www.ncbi.nlm.nih.gov/pubmed/27573873 https://www.ncbi.nlm.nih.gov/pubmed/25027398 https://www.ncbi.nlm.nih.gov/pubmed/23690045	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Verrucarin A, a protein synthesis inhibitor, induces growth inhibition and apoptosis in breast cancer cell lines MDA-MB-231 and T47D.	2013-09	23690045
Evaluation of the antiviral activity against Junin virus of macrocyclic trichothecenes produced by the hypocrealean epibiont of Baccharis coridifolia.	2002-03	11914955

Patents

Sample Use Guides

In Vivo Use Guide

Mice: LD50 = 1.5 mg/kg

Route of Administration: Intravenous

In Vitro Use Guide

Doses of roridin A and verrucarin A which inhibited [3H]thymidine uptake by 50%, as averaged from this mitogen panel, were 20 and 9 pg/ml, respectively.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:43:05 GMT 2025` Edited by `admin` on `Mon Mar 31 22:43:05 GMT 2025`
Record UNII	OL62X66O4I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VERRUCARIN A

Common Name

English

NSC-126728

Preferred Name

English

MUCONOMYCIN

Common Name

English

NSC-200736

Code

English

SPIRO(16,18-METHANO-1H,3H,23H-(1,6,12)TRIOXACYCLOOCTADECINO(3,4-D)(1)BENZOPYRAN-17(18H),2'-OXIRANE)-3,9,14-TRIONE, 4,5,6,7,16,16A,19A,22-OCTAHYDRO-4-HYDROXY-5,16A,21-TRIMETHYL-, (4S,5R,10E,12Z,16R,16AS,17S,18R,19AR,23AR)-

Common Name

English

VERRUCARIN A [MI]

Common Name

English

VERRUCARINE A

Common Name

English

MUCONOMYCIN A

Common Name

English

Code System Code Type Description

CHEBI

230243