Grassypeptolide A

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Basic information

Standard SMILES: CC[C@H]1NC(=O)[C@@H]2CSC(=N2)[C@@H](Cc2ccccc2)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](Cc2ccccc2)OC(=O)[C@H](C)[C@@H](C)NC(=O)[C@@H]([C@@H](C)O)NC(=O)[C@@H](CC(C)C)N(C)C(=O)[C@@H]2CSC1=N2
InChIKey: KUUZFDUZAFJFSJ-IHTUVIFUSA-N
Molecular formula: C56H79N9O10S2
Average molar mass: 1,102.4 g/mol
Monoisotopic mass: 1,101.5391321

Overview

Grassypeptolide is a 31-membered macrocyclic cyclodepsipeptide isolated from the cyanobacterium Lyngbya confervoides and has been shown to exhibit antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is a cyclodepsipeptide and a macrocycle.

Names & identifiers

Preferred name: Grassypeptolide A
IUPAC: (2R,5R,9R,12S,18S,21S,24R,25R,28R,31R,34R)-9,21-dibenzyl-2-ethyl-28-[(1R)-1-hydroxyethyl]-10,19,24,25,32-pentamethyl-31-(2-methylpropyl)-18-propan-2-yl-22-oxa-7,36-dithia-3,10,16,19,26,29,32,37,38-nonazatetracyclo[32.2.1.15,8.012,16]octatriaconta-1(37),8(38)-diene-4,11,17,20,23,27,30,33-octone

Names & synonyms

Grassypeptolide ADTXSID901047216RefChem:922498DTXCID701528830(3R,4Z,7R,10R,11Z,14R,17R,20R,23R,24R,27S,30S,35aS)-3,27-dibenzyl-10-ethyl-20-((R)-1-hydroxyethyl)-17-isobutyl-30-isopropyl-2,16,23,24,29-pentamethyl-2,3,9,10,16,17,19,20,23,24,29,30,33,34,35,35a-hexadecahydro-1H,6H,13H,27H-4,7:11,14-di(azeno)pyrrolo(1,2-g)(1)oxa(13,20)dithia(4,7,10,17,24,27,30)heptaazacyclotritriacontin-1,8,15,18,21,25,28,31(7H,14H,22H)-octaoneGrassypeptolide(3R,7R,10R,14R,17R,20R,23R,24R,27S,30S,35aS)-3,27-dibenzyl-10-ethyl-20-[(1R)-1-hydroxyethyl]-2,16,23,24,29-pentamethyl-17-(2-methylpropyl)-30-(propan-2-yl)hexadecahydro-1H,6H,13H,27H-7,4:14,11-di(azeno)pyrrolo[1,2-g][1,13,20,4,7,10,17,24,27,30]oxadithiaheptaazacyclotritriacontine-1,8,15,18,21,25,28,31(7H,14H,22H)-octoneSCHEMBL29886538CHEBI:65980GLXC-15338Q271344801010433-25-6

Database identifiers

PubChem CID: 24809132
DTXSID: DTXSID901047216
ChEBI: CHEBI:65980

Properties

Computed structural properties

XLogP: 6.5
Topological polar surface area: 290 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 14
Rotatable bonds: 9
Heavy atoms: 77
Formal charge: 0
Complexity: 2,180

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Compound notes

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