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Phomopsinamine

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Phomopsinamine
Category Mycotoxins
Catalog number BBF-05250
CAS 89085-54-1
Molecular Weight 675.17
Molecular Formula C32H43ClN6O8
Purity >95% by HPLC

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Fermentation Lab

4 R&D and scale-up labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Phomopsinamine is a potent mycotoxin and an effective microtubule inhibitor produced by the fungus, Phomopsis leptostromiformis. Phomopsinamine is formed by hydrolysis of the dicarboxylic acid of phomopsin A.

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  • Properties
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Synonyms Isoleucinamide, (βS)-3-chloro-β,5-dihydroxy-N-methyl-L-tyrosyl-3,4-didehydro-L-valyl-3-hydroxy-L-isoleucyl-3,4-didehydro-L-prolyl-2,3-didehydro-, cyclic (15→3)-ether, (2E)-; Phomopsinamine A; (2E)-(βS)-3-chloro-β,5-dihydroxy-N-methyl-L-tyrosyl-3,4-didehydro-L-valyl-3-hydroxy-L-isoleucyl-3,4-didehydro-L-prolyl-2,3-didehydro-isoleucinamide, cyclic (15→3)-ether; (S)-N-((E)-1-amino-3-methyl-1-oxopent-2-en-2-yl)-1-((3R,4S,7S,10S,11S)-15-chloro-3-ethyl-16,11-dihydroxy-3-methyl-10-(methylamino)-6,9-dioxo-7-(prop-1-en-2-yl)-2-oxa-5,8-diaza-1(1,3)-benzenacycloundecaphane-4-carbonyl)-2,5-dihydro-1H-pyrrole-2-carboxamide
Storage Store at -20°C
IUPAC Name (2S)-N-[(E)-1-amino-3-methyl-1-oxopent-2-en-2-yl]-1-[(3R,4S,7S,10S,11S)-14-chloro-3-ethyl-11,15-dihydroxy-3-methyl-10-(methylamino)-6,9-dioxo-7-prop-1-en-2-yl-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(15),12(16),13-triene-4-carbonyl]-2,5-dihydropyrrole-2-carboxamide
Canonical SMILES CCC(=C(C(=O)N)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
InChI InChI=1S/C32H43ClN6O8/c1-8-16(5)22(27(34)42)37-28(43)19-11-10-12-39(19)31(46)26-32(6,9-2)47-20-14-17(13-18(33)25(20)41)24(40)23(35-7)30(45)36-21(15(3)4)29(44)38-26/h10-11,13-14,19,21,23-24,26,35,40-41H,3,8-9,12H2,1-2,4-7H3,(H2,34,42)(H,36,45)(H,37,43)(H,38,44)/b22-16+/t19-,21-,23-,24-,26+,32+/m0/s1
InChI Key YFIIICIITZPYSM-OIXMZTBHSA-N
Appearance Solid
Boiling Point 1022.7±65.0°C at 760 mmHg
Density 1.4±0.1 g/cm3
Solubility Soluble in DMSO, Methanol
1. Interaction of phomopsin A and related compounds with purified sheep brain tubulin
E Lacey, J A Edgar, C C Culvenor Biochem Pharmacol. 1987 Jul 1;36(13):2133-8. doi: 10.1016/0006-2952(87)90141-9.
Phomopsins comprise a family of peptide mycotoxins containing a 13-membered ring formed by an ether bridge, produced by the fungus Phomopsis leptostromiformis, the causal agent in lupin poisoning (lupinosis). The biochemical actions of two naturally occurring phomopsins, phomopsin A and B, and the chemical derivatives, phomopsinamine A and octahydrophomopsin A, on purified sheep brain tubulin were investigated. All analogues were potent microtubule inhibitors, blocking the polymerization of tubulin at concentrations of less than 1 microM. They inhibited [3H]vinblastine binding to tubulin and, in common with vinblastine and its competitive inhibitor maytansine, enhanced the binding of [3H]colchicine to tubulin. It is postulated that phomopsin A and its analogues exert their action on tubulin by interaction at or near the vinblastine binding site. Two possible mechanisms for the interaction between vinblastine or phomopsins and colchicine binding to tubulin are proposed.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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