6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-6',7'-dihydrospiro[cyclopropane-1,5'-indene]-7'-one

• ChemBase ID: 171747
• Molecular Formular: C15H18O3
• Molecular Mass: 246.30162
• Monoisotopic Mass: 246.12559444
• SMILES: C1(C2(C(=C3C(=CC(=C3CO)C)C1=O)C)CC2)(O)C
• Canonical SMILES: OCC1=C(C)C=C2C1=C(C)C1(C(C2=O)(C)O)CC1
• InChI: InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3
• InChIKey: NICJCIQSJJKZAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-6',7'-dihydrospiro[cyclopropane-1,5'-indene]-7'-one
• IUPAC Traditional name: 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-indene]-7'-one
• Synonyms: 6'-Hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one; (+/-)-Hydroxymethylacylfulvene; rac-Irofulven

Database IDs

• CAS Number: 187277-46-9
• PubChem SID: 164227657
• PubChem CID: 3844471

CALCULATED PROPERTIES

• Acid pKa: 12.765375
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.6721893
• LogD (pH = 7.4): 0.6721875
• Log P: 0.67218935
• Molar Refractivity: 70.9055 cm^3
• Polarizability: 26.758808 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I769490

rac-Irofulven is a semi-synthetic antitumor agent derived from Illudin S. Inhibits DNA synthesis and induces apoptosis in tumor cells. Antineoplastic.

REFERENCES

• Woynarowski, J.M., et al.: Biochem. Pharmacol., 54, 1181 (1997)
• Alexandre, J., et al.: Clin. Cancer Res., 10, 3377 (1997)
• Senzer, N., et al.: Am. J. Clin. Oncol., 28, 36 (1997)