(1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-({[2-(4-hydroxy-3-methoxyphenyl)acetyl]oxy}methyl)-4,12,12,15-tetramethyl-14-(nonanoyloxy)-5-oxotetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dien-13-yl nonanoate

• ChemBase ID: 134105
• Molecular Formular: C47H68O11
• Molecular Mass: 809.03622
• Monoisotopic Mass: 808.476163
• SMILES: CCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)COC(=O)Cc2ccc(c(c2)OC)O)[C@H]2[C@@]1(C2(C)C)OC(=O)CCCCCCCC)O)C
• Canonical SMILES: CCCCCCCCC(=O)O[C@@]12[C@H](OC(=O)CCCCCCCC)[C@@H](C)[C@]3([C@H]([C@@H]1C2(C)C)C=C(COC(=O)Cc1ccc(c(c1)OC)O)C[C@]1([C@H]3C=C(C1=O)C)O)O
• InChI: InChI=1S/C47H68O11/c1-8-10-12-14-16-18-20-38(49)57-43-31(4)46(54)34(41-44(5,6)47(41,43)58-39(50)21-19-17-15-13-11-9-2)25-33(28-45(53)37(46)24-30(3)42(45)52)29-56-40(51)27-32-22-23-35(48)36(26-32)55-7/h22-26,31,34,37,41,43,48,53-54H,8-21,27-29H2,1-7H3/t31-,34+,37-,41-,43-,45-,46-,47-/m1/s1
• InChIKey: FNUXVHZLPOXMCA-WARQNWORSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-({[2-(4-hydroxy-3-methoxyphenyl)acetyl]oxy}methyl)-4,12,12,15-tetramethyl-14-(nonanoyloxy)-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-13-yl nonanoate
• IUPAC Traditional name: (1S,2S,6R,10S,11R,13S,14R,15R)-1,6-dihydroxy-8-({[2-(4-hydroxy-3-methoxyphenyl)acetyl]oxy}methyl)-4,12,12,15-tetramethyl-14-(nonanoyloxy)-5-oxotetracyclo[8.5.0.0^2,^6.0^1^1,^1^3]pentadeca-3,8-dien-13-yl nonanoate
• Synonyms: PDNHV; Phorbol 12,13-dinonanoate 20-homovanillate

Database IDs

• MDL Number: MFCD02684410
• PubChem SID: 162228382; 24898086
• PubChem CID: 16219813

CALCULATED PROPERTIES

• Acid pKa: 9.9353485
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 8.651477
• LogD (pH = 7.4): 8.650236
• Log P: 8.651492
• Molar Refractivity: 220.8637 cm^3
• Polarizability: 87.35104 Å^3
• Polar Surface Area: 165.89 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetone: soluble; chloroform: soluble; DMSO: soluble; ethanol: soluble; methanol: soluble

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• 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 respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - P0234

Biochem/physiol Actions
Resiniferatoxin-type vanilloid phorbol ester with capsaicin-like selectivity for the vanilloid receptor.
Legal Information
Sold in France, Germany, Great Britain and Switzerland under a patent license, restricted to research use only, from Procyon Pharmaceuticals, Inc.