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

• ChemBase ID: 133718
• Molecular Formular: C49H72O11
• Molecular Mass: 837.08938
• Monoisotopic Mass: 836.50746312
• SMILES: CCCCCCCCCC(=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)CCCCCCCCC)O)C
• Canonical SMILES: CCCCCCCCCC(=O)O[C@@]12[C@H](OC(=O)CCCCCCCCC)[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/C49H72O11/c1-8-10-12-14-16-18-20-22-40(51)59-45-33(4)48(56)36(43-46(5,6)49(43,45)60-41(52)23-21-19-17-15-13-11-9-2)27-35(30-47(55)39(48)26-32(3)44(47)54)31-58-42(53)29-34-24-25-37(50)38(28-34)57-7/h24-28,33,36,39,43,45,50,55-56H,8-23,29-31H2,1-7H3/t33-,36+,39-,43-,45-,47-,48-,49-/m1/s1
• InChIKey: DXGOIXWTPMLJIK-FPBOOSLESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• MDL Number: MFCD02684413
• PubChem SID: 162227995; 24899066
• PubChem CID: 10653082

CALCULATED PROPERTIES

• LogD (pH = 5.5): 9.540614
• LogD (pH = 7.4): 9.539373
• Log P: 9.540629
• Molar Refractivity: 230.0657 cm^3
• Polarizability: 91.02737 Å^3
• Polar Surface Area: 165.89 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false
• Acid pKa: 9.9353485
• H Acceptors: 8
• H Donor: 3

PROPERTIES

Physical Property

• Solubility: chloroform: soluble; DMSO: soluble; ethanol: soluble; H2O: insoluble; 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, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: rat ... Trpv1(83810)

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - P9983

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.