(3Z,5Z,9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-8,11,17-trimethylidene-20-[(2R,3S)-3-[(2S)-pentan-2-yl]oxiran-2-yl]-1-oxacycloicosa-3,5,14-trien-2-one

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Basic information

CAS: 106463-75-6
Standard SMILES: C=C1C/C=C\[C@H](O)[C@@H](O)C(=C)[C@H](O)[C@@H](O)C(=C)C/C=C\C(C)=C/C(=O)O[C@@H]([C@@H]2O[C@H]2[C@@H](C)CCC)[C@@H](C)C1
InChIKey: NFOKXEYWZUZJRF-RPNMCIEKSA-N
Molecular formula: C31H46O7
Average molar mass: 530.7 g/mol
Monoisotopic mass: 530.3243538

Names & identifiers

Preferred name: (3Z,5Z,9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-8,11,17-trimethylidene-20-[(2R,3S)-3-[(2S)-pentan-2-yl]oxiran-2-yl]-1-oxacycloicosa-3,5,14-trien-2-one
IUPAC: (3Z,5Z,9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-8,11,17-trimethylidene-20-[(2R,3S)-3-[(2S)-pentan-2-yl]oxiran-2-yl]-1-oxacycloicosa-3,5,14-trien-2-one
English name: (3E,5E,9S,10S,12S,13S,14E,19S,20R)-4,19-Dimethyl-20-[(2R,3S)-3-[(1S)-1-methylbutyl]oxiranyl]-9,10,12,13-tetrahydroxy-8,11,17-tri(methylene)oxacycloicosa-3,5,14-triene-2-one
Molecular formula: C31H46O7
Molecular weight: 530.69

Names & synonyms

(3Z,5Z,9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-8,11,17-trimethylidene-20-[(2R,3S)-3-[(2S)-pentan-2-yl]oxiran-2-yl]-1-oxacycloicosa-3,5,14-trien-2-one(3E,5E,9S,10S,12S,13S,14E,19S,20R)-4,19-Dimethyl-20-[(2R,3S)-3-[(1S)-1-methylbutyl]oxiranyl]-9,10,12Oxacycloeicosa-3,5,14-trien-2-one, 9,10,12,13-tetrahydroxy-4,19-dimethyl-20-((2R,3S)-3-((1S)-1-methylbutyl)oxiranyl)-8,11,17-tris(methylene)-, (3E,5E,9S,10S,12S,13S,14E,19S,20R)-Amphidinolide A(3E,5E,9S,10S,12S,13S,14E,19S,20R)-4,19-Dimethyl-20-[(2R,3S)-3-[(1S)-1-methylbutyl]oxiranyl]-9,10,12,13-tetrahydroxy-8,11,17-tri(methylene)oxacycloicosa-3,5,14-triene-2-oneOxacycloeicosa-3,5,14-trien-2-one, 9,10,12,13-tetrahydroxy-4,19-dimethyl-20-[(2R,3S)-3-[(1S)-1-methylbutyl]-2-oxiranyl]-8,11,17-tris(methylene)-, (3E,5E,9S,10S,12S,13S,14E,19S,20R)-

Database identifiers

CAS: 106463-75-6

Properties

Computed structural properties

XLogP: 3.5
Topological polar surface area: 120 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 7
Rotatable bonds: 4
Heavy atoms: 38
Formal charge: 0
Complexity: 946

Physicochemical properties

Boiling point: 706.6 · 706.6±60.0 °C(Predicted)
Density: 1.13 · 1.13±0.1 g/cm3(Predicted)
pka: 13.66 · 13.66±0.70(Predicted)

Chemistry & industry

Applications

DescriptionAmphidinolide A is a novel 20-membered macrolide. It has been shown to exhibit antineoplastic activity.

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Compound notes

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