CYTOCHALASIN A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H35NO5
Molecular Weight	477.5919
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@]24OC(=O)\C=C\C(=O)CCC[C@@H](C)C\C=C\[C@H]4[C@H](O)C1=C

InChI

InChIKey=ZMAODHOXRBLOQO-TZVKRXPSSA-N

InChI=1S/C29H35NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18-19,23-24,26-27,33H,3,7,9-10,13,17H2,1-2H3,(H,30,34)/b14-8+,16-15+/t18-,19-,23+,24+,26+,27-,29-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C29H35NO5
Molecular Weight	477.5919
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6067685
Curator's Comment: Description was created based on several sources, including https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/c8273pis.pdf | https://www.ncbi.nlm.nih.gov/pubmed/7199054 | https://www.ncbi.nlm.nih.gov/pubmed/7061857 | https://www.ncbi.nlm.nih.gov/pubmed/422516 | https://www.ncbi.nlm.nih.gov/pubmed/7174519 | https://www.ncbi.nlm.nih.gov/pubmed/1624371

Cytochalasin A is a metabolite of the fungus Drechslera (previously Heiminthosporium) dematioideum. Cytochalasin A is effective as an inhibitor of the cytoskeletal reorganisation. Cytochalasin A is able to inhibit cell proliferation. Cytochalasin A exerts antibacterial action toward gram-positive bacteria. Cytochalasin A was active as an inhibitor of HIV-1 protease.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adenosine A1 receptor 54 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27043138	Binding Agent 1076	1.9 µM [Ki]
cytoskeleton organization 1 Target ID: GO:0007010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9537763 \| https://www.ncbi.nlm.nih.gov/pubmed/1033438 \| https://www.ncbi.nlm.nih.gov/pubmed/7199054	Inhibitor 8504
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7061857	Inhibitor 8504	2.0 µM [Ki]
Human immunodeficiency virus type 1 protease 36 Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1624371	Inhibitor 8504	3.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
A SURVEY OF NONXANTHINE DERIVATIVES AS ADENOSINE RECEPTOR LIGANDS.	2016-04-05	27043138
Effect of cytochalasin A on apical growth, actin cytoskeleton organization and enzyme secretion in Aspergillus nidulans.	1998-01	9537763
L-696,474, a novel cytochalasin as an inhibitor of HIV-1 protease. III. Biological activity.	1992-05	1624371
Structural features of cytochalasins responsible for gram-positive bacterial inhibitions.	1982-10	7174519
Correlation between effects of 24 different cytochalasins on cellular structures and cellular events and those on actin in vitro.	1982-01	7199054
Cytochalasin A inhibits B-lymphocyte capping and activation by antigens.	1981-08	6974687
Effects of cytochalasins on mammalian cells.	1967-01-21	6067685

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Cytochalasin A at 5 to 25 ug/ml inhibited the growth of three gram-positive bacteria, Arthrobacter sialophilus, Staphyloccus aureus, and Bacillus amyloliquifaciens, but had little or no effect on the growth of three gram-negative bacteria, Excherichia coli, Pseudomonas maltophilia, and Aeromonas proteolytica.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:10:10 GMT 2025` Edited by `admin` on `Mon Mar 31 19:10:10 GMT 2025`
Record UNII	BV8WQ9500E
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CYTOCHALASIN A

Common Name

English

NSC-174119

Preferred Name

English

5,5-DIDEHYDROPHOMIN

Systematic Name

English

5-DEHYDROPHOMIN

Systematic Name

English

2H-OXACYCLOTETRADECINO(2,3-D)ISOINDOLE-2,5,18-TRIONE, 6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-13-HYDROXY-9,15-DIMETHYL-14-METHYLENE-16-(PHENYLMETHYL)-, (3E,9R,11E,12AS,13S,15S,15AS,16S,18AS)-

Systematic Name

English

DEHYDROPHOMIN

Common Name

English

2H-OXACYCLOTETRADECINO(2,3-D)ISOINDOLE-2,5,18-TRIONE, 6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-13-HYDROXY-9,15-DIMETHYL-14-METHYLENE-16-(PHENYLMETHYL)-, (9R-(3E,9R*,11E,12AS*,13S*,15S*,15AS*,16S*,18AS*))-

Systematic Name

English

24-OXA(14)CYTOCHALASA-6(12),13,21-TRIENE-1,20,23-TRIONE, 7-HYDROXY-16-METHYL-10-PHENYL-, (7S,13E,16R,21E)-

Systematic Name

English

PHOMIN, 5,5-DIDEHYDRO-

Systematic Name

English

2H-OXACYCLOTETRADECINO(2,3-D)ISOINDOLE-2,5,18-TRIONE, 16-BENZYL-6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-13-HYDROXY-9,15-DIMETHYL-14-METHYLENE-

Systematic Name

English

Code System Code Type Description

CAS

14110-64-6