(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-8-formyl-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-14-yl tetradecanoate

• ChemBase ID: 153433
• Molecular Formular: C36H54O8
• Molecular Mass: 614.80916
• Monoisotopic Mass: 614.38186869
• SMILES: CCCCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)C=O)[C@H]2[C@@]1(C2(C)C)OC(=O)C)O)C
• Canonical SMILES: CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)C)C3(C)C)C=C(C[C@]1([C@H]2C=C(C1=O)C)O)C=O
• InChI: InChI=1S/C36H54O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,22,24,27-28,30,32,41-42H,7-18,21H2,1-6H3/t24-,27+,28-,30?,32-,34-,35-,36-/m1/s1
• InChIKey: AHLWZBVXSWOPPL-CMMOZPOHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-8-formyl-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-14-yl tetradecanoate
• IUPAC Traditional name: (1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-8-formyl-1,6-dihydroxy-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-14-yl tetradecanoate
• Synonyms: 20-Deoxy-20-oxophorbol 12-myristate 13-acetate

Database IDs

• CAS Number: 30358-69-1
• MDL Number: MFCD00036781
• PubChem SID: 162247572; 24898928
• PubChem CID: 16219903

CALCULATED PROPERTIES

• Acid pKa: 12.559363
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 6.0060067
• LogD (pH = 7.4): 6.006004
• Log P: 6.0060067
• Molar Refractivity: 168.3354 cm^3
• Polarizability: 66.57002 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 26/27/28-36/37/38
• Safety Statements: 26-27-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H315-H319-H330-H335
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C36H54O8

DETAILS

Sigma Aldrich - P9893

Application
Reduction with tritiated NaBH4 yields tritiated phorbol 12-myristate 13-acetate that can be used for receptor binding studies