2-{2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

• ChemBase ID: 160581
• Molecular Formular: C23H20O6
• Molecular Mass: 392.4013
• Monoisotopic Mass: 392.12598836
• SMILES: c1c(ccc(c1)/C=C/C(=O)OC(C1Oc2c(C1)c1c(cc2)ccc(=O)o1)(C)C)O
• Canonical SMILES: O=C(OC(C1Oc2c(C1)c1oc(=O)ccc1cc2)(C)C)/C=C/c1ccc(cc1)O
• InChI: InChI=1S/C23H20O6/c1-23(2,29-21(26)11-5-14-3-8-16(24)9-4-14)19-13-17-18(27-19)10-6-15-7-12-20(25)28-22(15)17/h3-12,19,24H,13H2,1-2H3/b11-5+
• InChIKey: YPULLITUOWRRPG-VZUCSPMQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
• IUPAC Traditional name: 2-{2-oxo-8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
• Synonyms: (2E)-3-(4-Hydroxyphenyl)-2-propenoic Acid 1-[(8S)-8,9-Dihydro-2-oxo-2H-furo[2,3-h]-1-benzopyran-8-yl]-1-methylethyl Ester; A2M7; Angelmarin; (+)-Angelmarin

Database IDs

• CAS Number: 876384-53-1
• PubChem SID: 162254716
• PubChem CID: 71313386

CALCULATED PROPERTIES

• Acid pKa: 9.3985615
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.4626646
• LogD (pH = 7.4): 4.458409
• Log P: 4.462719
• Molar Refractivity: 107.8895 cm^3
• Polarizability: 41.177975 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A637600

A novel anti-cancer agent able to eliminate the tolerance of cancer cells to nutrient starvation.

REFERENCES

• Helmlinger, G., et al.: Nat. Med., 3, 177 (1997)
• Izuishi, K., et al.: Cancer Res., 60, 6201 (1997)
• Li, D., et al.: Lancet, 363, 1049 (1997)
• Lu, J., et al.: Cancer Sci., 95, 547 (1997)
• Morita, H., et al.: Bioorg. Med. Chem. Lett., 14, 3665 (1997)