15-hydroxy-3,17-dimethoxy-5-methyl-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: 154537
• Molecular Formular: C27H28O9
• Molecular Mass: 496.50582
• Monoisotopic Mass: 496.17333248
• SMILES: Cc1cc2c(c3cc(c4c(ccc(c4c3oc2=O)[C@H]2[C@@H]([C@]([C@H]([C@H](O2)C)O)(C)O)O)O)OC)c(c1)OC
• 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
• InChI: InChI=1S/C27H28O9/c1-11-8-15-19(17(9-11)33-4)14-10-18(34-5)21-16(28)7-6-13(20(21)22(14)36-26(15)31)23-25(30)27(3,32)24(29)12(2)35-23/h6-10,12,23-25,28-30,32H,1-5H3/t12-,23+,24+,25+,27-/m1/s1
• InChIKey: BJPYMDSMDBCKEP-QSMCFSHASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 15-hydroxy-3,17-dimethoxy-5-methyl-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: 15-hydroxy-3,17-dimethoxy-5-methyl-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 B

Database IDs

• CAS Number: 83852-56-6
• MDL Number: MFCD07370132
• PubChem SID: 162248676; 24892870
• PubChem CID: 16219149

CALCULATED PROPERTIES

• Acid pKa: 8.522798
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 2.3790743
• LogD (pH = 7.4): 2.3481472
• Log P: 2.3794835
• Molar Refractivity: 129.5506 cm^3
• Polarizability: 52.740417 Å^3
• Polar Surface Area: 134.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

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): C27H28O9

DETAILS

Sigma Aldrich - C6491

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.