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

[H][C@]12C[C@H]3O[C@]4([H])C=C(C)CC[C@]4(COC(=O)[C@@H](O)[C@H](C)CCOC(=O)\C=C\C=CC(=O)O1)[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 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27849335 \| https://www.ncbi.nlm.nih.gov/pubmed/23690045	Activator 1430
Protein biosynthesis 8 Target ID: Protein biosynthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/16869484	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 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
Evaluation of the antiviral activity against Junin virus of macrocyclic trichothecenes produced by the hypocrealean epibiont of Baccharis coridifolia.	2002 Mar	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 `Sat Dec 16 09:33:05 GMT 2023` Edited by `admin` on `Sat Dec 16 09:33:05 GMT 2023`
Record UNII	OL62X66O4I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VERRUCARIN A

Common 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

NSC-126728

Code

English

VERRUCARINE A

Common Name

English

MUCONOMYCIN A

Common Name

English

Code System Code Type Description

CHEBI

230243