(2E,4E,6R)-N-[(5S,6S)-5-hydroxy-5-[(1E,3E,5E)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide

• ChemBase ID: 133154
• Molecular Formular: C31H38N2O7
• Molecular Mass: 550.64262
• Monoisotopic Mass: 550.26790157
• SMILES: CCCC[C@@H](C)/C=C(\C)/C=C(\C)/C(=O)NC1=C[C@]([C@@H]2C(C1=O)O2)(/C=C/C=C/C=C/C(=O)NC1=C(CCC1=O)O)O
• Canonical SMILES: CCCC[C@H](/C=C(/C=C(/C(=O)NC1=C[C@@](O)(/C=C/C=C/C=C/C(=O)NC2=C(O)CCC2=O)[C@@H]2C(C1=O)O2)\C)\C)C
• InChI: InChI=1S/C31H38N2O7/c1-5-6-11-19(2)16-20(3)17-21(4)30(38)32-22-18-31(39,29-28(40-29)27(22)37)15-10-8-7-9-12-25(36)33-26-23(34)13-14-24(26)35/h7-10,12,15-19,28-29,34,39H,5-6,11,13-14H2,1-4H3,(H,32,38)(H,33,36)/b8-7+,12-9+,15-10+,20-16+,21-17+/t19-,28?,29+,31+/m1/s1
• InChIKey: TWWQHCKLTXDWBD-WQAMNJLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6R)-N-[(5S,6S)-5-hydroxy-5-[(1E,3E,5E)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide
• IUPAC Traditional name: (2E,4E,6R)-N-[(5S,6S)-5-hydroxy-5-[(1E,3E,5E)-6-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)carbamoyl]hexa-1,3,5-trien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide
• Synonyms: Manumycin A from Streptomyces parvulus

Database IDs

• CAS Number: 52665-74-4
• MDL Number: MFCD00920782
• PubChem SID: 162227431; 24897011
• PubChem CID: 71308643

CALCULATED PROPERTIES

• Acid pKa: 9.044299
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 3.0566256
• LogD (pH = 7.4): 3.0470119
• Log P: 3.0567496
• Molar Refractivity: 159.4081 cm^3
• Polarizability: 58.463467 Å^3
• Polar Surface Area: 145.33 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - M6418

Biochem/physiol Actions
Potent inhibitor of Ras farnesyltransferase.