Cyclic hexapeptide antibiotic

Phomopsin A

Molecular Formula

C36H45ClN6O12

M.W.

789.20

CAS number

64925-80-0

Details

Source

Phomopsis leptostromiformis

Fermentek product Code

PHA-001

Brand/grade

For research

Specifications

Appearance

White powder

Purity by HPLC

≥98% ; refer to CoA for more data

Purity By TLC

≥98% ; refer to CoA for more data

Solubility test

Clear colorless solution at 10mg/ml of DMSO

Chemical identification

Names and identifiers

IUPAC: (2E)-2-{[(2E)-2-({[(2S)-1-{[(3R,4S,7S,10S,11S)-14-Chloro-3-ethyl-11,15-dihydroxy-7-isopropenyl-3-methyl-10-(methylamino)-6,9-dioxo-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-trien-4-yl]carbony l}-2,5-dihydro-1H-pyrrol-2-yl]carbonyl}amino)-3-methyl-2-pentenoyl]amino}-2-butenedioic acid

RTECS# SY2593000

Chemical name

Phomopsin A

Description

Cyclic hexapeptide antibiotic. Phomopsin A exhibits very strong inhibitory properties of microtubule assembly. It binds to tubulin at a site different from the colchicine binding site.

InChl Key

FAFRRYBYQKPKSY-AJSRVUJESA-N

Canonical SMILES

CCC(=C(C(=O)NC(=CC(=O)O)C(=O)O)NC(=O)C1C=CCN1C(=O)C2C(OC3=C(C(=CC(=C3)C(C(C(=O)NC(C(=O)N2)C(=C)C)NC)O)Cl)O)(C)CC)C

Isomeric SMILES

CC/C(=C(\C(=O)N/C(=C/C(=O)O)/C(=O)O)/NC(=O)[C@@H]1C=CCN1C(=O)[C@@H]2[C@@](OC3=C(C(=CC(=C3)[C@@H]([C@@H](C(=O)N[C@H](C(=O)N2)C(=C)C)NC)O)Cl)O)(C)CC)/C

Further Information

Solubility ( literature )

Soluble in Ethanol, DMSO and DMF. Sparingly siluble in water. Not stable in watery solutions. (lit).

Compound Classification

Classification by Bioactivity