(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-14-yl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

• ChemBase ID: 134032
• Molecular Formular: C42H56O8
• Molecular Mass: 688.88924
• Monoisotopic Mass: 688.39751875
• SMILES: C[C@@H]1[C@H]([C@@]2([C@H](C2(C)C)[C@H]2[C@]1([C@@H]1C=C(C(=O)[C@]1(CC(=C2)CO)O)C)O)OC(=O)C)OC(=O)/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(CCCC1(C)C)C
• Canonical SMILES: OCC1=C[C@H]2[C@H]3C([C@]3(OC(=O)C)[C@@H]([C@H]([C@@]2([C@H]2[C@@](C1)(O)C(=O)C(=C2)C)O)C)OC(=O)/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C)(C)C
• InChI: InChI=1S/C42H56O8/c1-24(16-17-31-26(3)15-12-18-38(31,7)8)13-11-14-25(2)19-34(45)49-37-28(5)41(48)32(35-39(9,10)42(35,37)50-29(6)44)21-30(23-43)22-40(47)33(41)20-27(4)36(40)46/h11,13-14,16-17,19-21,28,32-33,35,37,43,47-48H,12,15,18,22-23H2,1-10H3/b14-11+,17-16+,24-13+,25-19+/t28-,32+,33-,35?,37-,40-,41-,42-/m1/s1
• InChIKey: GTNCUWBKHZZECN-QHXPBLEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-14-yl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
• IUPAC Traditional name: (1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-14-yl (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
• Synonyms: Phorbol 12-retinoate 13-acetate

Database IDs

• CAS Number: 80188-99-4
• PubChem SID: 162228309; 24898977
• PubChem CID: 71308752

CALCULATED PROPERTIES

• Acid pKa: 12.57037
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 5.572415
• LogD (pH = 7.4): 5.572412
• Log P: 5.572415
• Molar Refractivity: 199.2275 cm^3
• Polarizability: 76.21096 Å^3
• Polar Surface Area: 130.36 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: yellow powder

Safety Information

• RTECS: VH6505000
• 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

DETAILS

Sigma Aldrich - P8780

Biochem/physiol Actions
Skin tumor promoter.1