[13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate

• ChemBase ID: 104587
• Molecular Formular: C37H40O9
• Molecular Mass: 628.7081
• Monoisotopic Mass: 628.26723286
• SMILES: COc1cc(CC(=O)OCC2=CC3C4OC5(Cc6ccccc6)OC4(CC(C)C3(O5)C3C=C(C)C(=O)C3(O)C2)C(=C)C)ccc1O
• Canonical SMILES: COc1cc(ccc1O)CC(=O)OCC1=CC2C3OC4(OC2(C2C(C1)(O)C(=O)C(=C2)C)C(CC3(O4)C(=C)C)C)Cc1ccccc1
• InChI: InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-27(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)13-22(3)32(34)40)20-43-31(39)16-25-11-12-28(38)29(15-25)42-5/h6-15,23,27,30,33,38,41H,1,16-20H2,2-5H3
• InChIKey: DSDNAKHZNJAGHN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
• IUPAC Traditional name: [13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
• Synonyms: RESINIFERATOXIN

Database IDs

• CAS Number: 57444-62-9
• PubChem SID: 162091606
• PubChem CID: 5148108

CALCULATED PROPERTIES

• Acid pKa: 9.935402
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 5.588857
• LogD (pH = 7.4): 5.587617
• Log P: 5.588873
• Molar Refractivity: 170.105 cm^3
• Polarizability: 66.35291 Å^3
• Polar Surface Area: 120.75 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: 95%

DETAILS

MP Biomedicals - 02156505

From Euphorbia poisonii
Purity: 95%
Diterpene ester related to phorbol^1 but apparently not tumorigenic.^2

REFERENCES

• Sorg, B., et al., J. Nat. Prod. , 45 : 347, (1982).
• Hergenhahn, M., et al., J. Cancer Res. Clin. Oncol. , 108 : 98, (1984).