(1S,2S,6S,10S,11R,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-5-one

• ChemBase ID: 133581
• Molecular Formular: C20H28O6
• Molecular Mass: 364.43272
• Monoisotopic Mass: 364.18858862
• 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)O)O
• Canonical SMILES: OCC1=C[C@H]2[C@@H]3[C@@](C3(C)C)(O)[C@@H]([C@H]([C@@]2([C@H]2[C@](C1)(O)C(=O)C(=C2)C)O)C)O
• InChI: InChI=1S/C20H28O6/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14?,16-,18+,19-,20-/m1/s1
• InChIKey: QGVLYPPODPLXMB-IVUHWGAKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6S,10S,11R,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-5-one
• IUPAC Traditional name: (1S,2S,6S,10S,11R,13S,14R,15R)-1,6,13,14-tetrahydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyltetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-5-one
• Synonyms: 4α,9α,12β,13α,20-pentahydroxytiglia-1,6-dien-3-one; 4α-PHR; Isophorbol; 4α-Phorbol

Database IDs

• CAS Number: 26241-63-4
• MDL Number: MFCD00036738
• PubChem SID: 162227858; 24898565
• PubChem CID: 71308688

CALCULATED PROPERTIES

• Acid pKa: 12.48295
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.7808828
• LogD (pH = 7.4): -0.78088635
• Log P: -0.7808827
• Molar Refractivity: 95.7774 cm^3
• Polarizability: 37.398468 Å^3
• Polar Surface Area: 118.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white

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 - P4888

Application
Phorbol that is not biologically active; can be used as a negative control