5-ethenyl-15-hydroxy-3,17-dimethoxy-12-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-4,6-dimethyloxan-2-yl]-9-oxatetracyclo[8.8.0.02,7.011,16]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one

• ChemBase ID: 154539
• Molecular Formular: C28H28O9
• Molecular Mass: 508.51652
• Monoisotopic Mass: 508.17333248
• SMILES: C[C@@H]1[C@@H]([C@@]([C@H]([C@@H](O1)c1ccc(c2c1c1c(cc2OC)c2c(cc(cc2OC)C=C)c(=O)o1)O)O)(C)O)O
• Canonical SMILES: COc1cc2c(c3c1c(O)ccc3[C@@H]1O[C@H](C)[C@@H]([C@@]([C@H]1O)(C)O)O)oc(=O)c1c2c(OC)cc(c1)C=C
• InChI: InChI=1S/C28H28O9/c1-6-13-9-16-20(18(10-13)34-4)15-11-19(35-5)22-17(29)8-7-14(21(22)23(15)37-27(16)32)24-26(31)28(3,33)25(30)12(2)36-24/h6-12,24-26,29-31,33H,1H2,2-5H3/t12-,24+,25+,26+,28-/m1/s1
• InChIKey: OMDANBMKOUVKAG-WZNMFJNZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethenyl-15-hydroxy-3,17-dimethoxy-12-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-4,6-dimethyloxan-2-yl]-9-oxatetracyclo[8.8.0.0^2,^7.0^1^1,^1^6]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one
• IUPAC Traditional name: 5-ethenyl-15-hydroxy-3,17-dimethoxy-12-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-4,6-dimethyloxan-2-yl]-9-oxatetracyclo[8.8.0.0^2,^7.0^1^1,^1^6]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one
• Synonyms: Chrysomycin A

Database IDs

• CAS Number: 82196-88-1
• MDL Number: MFCD07370133
• PubChem SID: 24892881; 162248678
• PubChem CID: 73468

CALCULATED PROPERTIES

• Acid pKa: 8.521034
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 2.6023533
• LogD (pH = 7.4): 2.571305
• Log P: 2.6027641
• Molar Refractivity: 134.1957 cm^3
• Polarizability: 54.485336 Å^3
• Polar Surface Area: 134.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; ethanol: moderately soluble; methanol: moderately soluble
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C28H28O9

DETAILS

Sigma Aldrich - C6616

Biochem/physiol Actions
Antibiotic from Streptomyces sp. Inhibits the catalytic activity of human topoisomerase II. Exhibits antitumor activity against human cell lines K562, HT29, MCF7, PC6, and MKN28.