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

• ChemBase ID: 133401
• Molecular Formular: C28H38O8
• Molecular Mass: 502.59652
• Monoisotopic Mass: 502.25666818
• SMILES: CCCC(=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)CCC)O)C
• Canonical SMILES: CCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@H]([C@H]3[C@]1(OC(=O)CCC)C3(C)C)C=C(C[C@]1([C@H]2C=C(C1=O)C)O)C=O
• InChI: InChI=1S/C28H38O8/c1-7-9-20(30)35-24-16(4)27(34)18(22-25(5,6)28(22,24)36-21(31)10-8-2)12-17(14-29)13-26(33)19(27)11-15(3)23(26)32/h11-12,14,16,18-19,22,24,33-34H,7-10,13H2,1-6H3/t16-,18+,19-,22?,24-,26-,27-,28-/m1/s1
• InChIKey: BSSVCYJMQUYSRI-AHNFSZCQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6R,10S,11R,13S,14R,15R)-14-(butanoyloxy)-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-13-yl butanoate
• IUPAC Traditional name: (1S,2S,6R,10S,11R,13S,14R,15R)-14-(butanoyloxy)-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-13-yl butanoate
• Synonyms: PDBuAL; 20-Deoxy-20-oxophorbol 12,13-dibutyrate

Database IDs

• CAS Number: 100930-03-8
• MDL Number: MFCD00036791
• PubChem SID: 162227678; 24898581
• PubChem CID: 16219862

CALCULATED PROPERTIES

• Acid pKa: 12.559363
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.7054245
• LogD (pH = 7.4): 2.7054217
• Log P: 2.7054245
• Molar Refractivity: 131.5533 cm^3
• Polarizability: 51.885517 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 9
• 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

DETAILS

Sigma Aldrich - P5026

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