[(1R,2R,6R,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(3-hydroxy-5-methoxyphenyl)acetate

• ChemBase ID: 133756
• Molecular Formular: C37H40O9
• Molecular Mass: 628.7081
• Monoisotopic Mass: 628.26723286
• SMILES: C[C@@H]1C[C@]2([C@H]3C4[C@]1([C@@H]1C=C(C(=O)[C@]1(CC(=C4)COC(=O)Cc1cc(cc(c1)OC)O)O)C)O[C@](O3)(O2)Cc1ccccc1)C(=C)C
• Canonical SMILES: COc1cc(CC(=O)OCC2=CC3[C@H]4O[C@]5(O[C@]3([C@H]3[C@@](C2)(O)C(=O)C(=C3)C)[C@@H](C[C@@]4(O5)C(=C)C)C)Cc2ccccc2)cc(c1)O
• InChI: InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-29(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)11-22(3)32(34)40)20-43-31(39)15-25-12-27(38)16-28(13-25)42-5/h6-14,16,23,29-30,33,38,41H,1,15,17-20H2,2-5H3/t23-,29?,30-,33-,34-,35-,36-,37-/m1/s1
• InChIKey: IKYCZSUNGFRBJS-PMIKMUNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R,2R,6R,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^1,^1^0.0^2,^6.0^1^1,^1^5]octadeca-3,8-dien-8-yl]methyl 2-(3-hydroxy-5-methoxyphenyl)acetate
• IUPAC Traditional name: [(1R,2R,6R,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^1,^1^0.0^2,^6.0^1^1,^1^5]octadeca-3,8-dien-8-yl]methyl 2-(3-hydroxy-5-methoxyphenyl)acetate
• Synonyms: Resiniferatoxin aus Euphorbia poisonii; Resiniferatoxin

Database IDs

• CAS Number: 57444-62-9
• MDL Number: MFCD00135927
• Beilstein Number: 5371150
• PubChem SID: 24899411; 162228033
• PubChem CID: 16219935

CALCULATED PROPERTIES

• Acid pKa: 9.390471
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 5.588817
• LogD (pH = 7.4): 5.5844836
• Log P: 5.588873
• Molar Refractivity: 170.105 cm^3
• Polarizability: 66.35148 Å^3
• Polar Surface Area: 120.75 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: CY1633700
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-35
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• 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

Pharmacology Properties

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

Product Information

• Purity: ~95%; ≥95% (HPLC)
• Biological Source: from Euphorbia poisonii
• Empirical Formula (Hill Notation): C37H40O9

DETAILS

Sigma Aldrich - R8756

Biochem/physiol Actions
Potent VR1 vanilloid receptor agonist that has been used to label the vanilloid receptor in sensory ganglia; activates protein kinase C. Diterpene ester that is related to phorbol, but is not tumorigenic.

Sigma Aldrich - 83590

Other Notes
Phorbol-related diterpene ester of the daphnane type. Highly inflammatory, skin irritant (ID5/50 16 fmole/ear)1,2; Review (Pro-inflammatory, tumor-promoting and anti-tumor diterpenes of the plant families Euphorbiaceae and Thymeleaceae3