(4S,5S)-10-[(2R,3S,6S,8S,9R)-9-butyl-8-(4-carboxy-3-methylbuta-1,3-dien-1-yl)-9-[(3-carboxypropanoyl)oxy]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid

• ChemBase ID: 154540
• Molecular Formular: C36H52O11
• Molecular Mass: 660.79148
• Monoisotopic Mass: 660.35096248
• SMILES: CCCC[C@]1(CC[C@]2(CC[C@@H]([C@H](O2)C/C=C(\C)/C=C/[C@@H]([C@@H](C)/C=C/C(=O)O)O)C)O[C@H]1/C=C/C(=C/C(=O)O)/C)OC(=O)CCC(=O)O
• Canonical SMILES: CCCC[C@]1(CC[C@@]2(O[C@H]1/C=C/C(=C/C(=O)O)/C)CC[C@@H]([C@H](O2)C/C=C(/C=C/[C@@H]([C@H](/C=C/C(=O)O)C)O)\C)C)OC(=O)CCC(=O)O
• InChI: InChI=1S/C36H52O11/c1-6-7-19-35(47-34(44)17-16-32(40)41)21-22-36(46-30(35)14-10-25(3)23-33(42)43)20-18-27(5)29(45-36)13-9-24(2)8-12-28(37)26(4)11-15-31(38)39/h8-12,14-15,23,26-30,37H,6-7,13,16-22H2,1-5H3,(H,38,39)(H,40,41)(H,42,43)/t26-,27-,28-,29+,30-,35+,36-/m0/s1
• InChIKey: ZESGNAJSBDILTB-LJXMMUGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S)-10-[(2R,3S,6S,8S,9R)-9-butyl-8-(4-carboxy-3-methylbuta-1,3-dien-1-yl)-9-[(3-carboxypropanoyl)oxy]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid
• IUPAC Traditional name: (4S,5S)-10-[(2R,3S,6S,8S,9R)-9-butyl-8-(4-carboxy-3-methylbuta-1,3-dien-1-yl)-9-[(3-carboxypropanoyl)oxy]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid
• Synonyms: Reveromycin A

Database IDs

• CAS Number: 134615-37-5
• MDL Number: MFCD00912537
• PubChem SID: 24899342; 162248679
• PubChem CID: 9939559

CALCULATED PROPERTIES

• Acid pKa: 3.7685864
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 2.3696544
• LogD (pH = 7.4): -2.7822666
• Log P: 5.9440227
• Molar Refractivity: 179.409 cm^3
• Polarizability: 68.74923 Å^3
• Polar Surface Area: 176.89 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; ethanol: soluble; ethyl acetate: soluble; methanol: soluble
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C36H52O11

DETAILS

Sigma Aldrich - R0654

Analysis Note
Avoid acidic conditions.
Biochem/physiol Actions
Reveromycin A is a polyketide antibiotic from Streptomyces sp. Epidermal growth factor (EGF) inhibitor; apoptosis inducer; G1 phase cell cycle inhibitor having antiproliferative behavior against human cell lines KB and K562 as well as antifungal activity.