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

[H][C@]12[C@H](CC3=CC=CC=C3)NC(=O)[C@]14OC(=O)\C=C\C(=O)CCC[C@@H](C)C\C=C\[C@@]4([H])[C@H](O)C(=C)[C@H]2C

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

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 50 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27043138	Binding Agent 1064	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 8297
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7061857	Inhibitor 8297	2.0 µM [Ki]
Human immunodeficiency virus type 1 protease 35 Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1624371	Inhibitor 8297	3.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Effects of cytochalasins on mammalian cells.	1967 Jan 21	6067685
Cytochalasin A inhibits B-lymphocyte capping and activation by antigens.	1981 Aug	6974687
Correlation between effects of 24 different cytochalasins on cellular structures and cellular events and those on actin in vitro.	1982 Jan	7199054
Structural features of cytochalasins responsible for gram-positive bacterial inhibitions.	1982 Oct	7174519
L-696,474, a novel cytochalasin as an inhibitor of HIV-1 protease. III. Biological activity.	1992 May	1624371
A SURVEY OF NONXANTHINE DERIVATIVES AS ADENOSINE RECEPTOR LIGANDS.	1996	27043138
Effect of cytochalasin A on apical growth, actin cytoskeleton organization and enzyme secretion in Aspergillus nidulans.	1998 Jan	9537763

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.

Name

Type

Language

CYTOCHALASIN A

Common 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

NSC-174119

Code

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

EPA CompTox

DTXSID40101758