(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-(2-methylbut-2-enamido)-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate

• ChemBase ID: 154993
• Molecular Formular: C45H53NO14
• Molecular Mass: 831.90062
• Monoisotopic Mass: 831.34660538
• SMILES: C/C=C(\C(=O)N[C@H]([C@@H](O)C(=O)O[C@@H]1C(=C2C([C@@](C1)([C@H](C1[C@]3([C@H](OC3)C[C@@H]([C@]1(C(=O)[C@@H]2OC(=O)C)C)O)OC(=O)C)OC(=O)c1ccccc1)O)(C)C)C)c1ccccc1)/C
• Canonical SMILES: C/C=C(\C(=O)N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)C3[C@@]4(CO[C@@H]4C[C@@H]([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)C)O)OC(=O)C)O)c1ccccc1)/C
• InChI: InChI=1S/C45H53NO14/c1-9-23(2)39(52)46-33(27-16-12-10-13-17-27)34(50)41(54)58-29-21-45(55)38(59-40(53)28-18-14-11-15-19-28)36-43(8,30(49)20-31-44(36,22-56-31)60-26(5)48)37(51)35(57-25(4)47)32(24(29)3)42(45,6)7/h9-19,29-31,33-36,38,49-50,55H,20-22H2,1-8H3,(H,46,52)/t29-,30-,31+,33-,34+,35+,36?,38-,43+,44-,45+/m0/s1
• InChIKey: DBXFAPJCZABTDR-KWHFJPKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-(2-methylbut-2-enamido)-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• IUPAC Traditional name: (1S,2S,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-{[(2R,3S)-2-hydroxy-3-(2-methylbut-2-enamido)-3-phenylpropanoyl]oxy}-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^3,^1^0.0^4,^7]heptadec-13-en-2-yl benzoate
• Synonyms: NSC 318735; Cephalomannine

Database IDs

• CAS Number: 71610-00-9
• MDL Number: MFCD01075131
• PubChem SID: 162249131; 24724441
• PubChem CID: 71312047

CALCULATED PROPERTIES

• Acid pKa: 10.363954
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 3.2230601
• LogD (pH = 7.4): 3.2226717
• Log P: 3.223144
• Molar Refractivity: 212.3023 cm^3
• Polarizability: 84.30143 Å^3
• Polar Surface Area: 221.29 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble14 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 37/38-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C45H53NO14

DETAILS

Sigma Aldrich - C4991

Biochem/physiol Actions
Cephalomannine is a taxol derivative with antitumor, antiproliferative properties.