2-[(3S,4R,5S,6S,7E,9E,11E)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methyl-4H-chromen-4-one

• ChemBase ID: 177881
• Molecular Formular: C30H42O7
• Molecular Mass: 514.65028
• Monoisotopic Mass: 514.29305368
• SMILES: c1(cc(c2c(c1O)oc(c(c2=O)C)CC[C@@H]([C@H]([C@@H]([C@H](/C=C/C=C/C(=C/C)/C)OC)C)OC)C)OC)OC
• Canonical SMILES: C/C=C(/C=C/C=C/[C@@H]([C@H]([C@@H]([C@H](CCc1oc2c(O)c(OC)cc(c2c(=O)c1C)OC)C)OC)C)OC)\C
• InChI: InChI=1S/C30H42O7/c1-10-18(2)13-11-12-14-22(33-6)21(5)29(36-9)19(3)15-16-23-20(4)27(31)26-24(34-7)17-25(35-8)28(32)30(26)37-23/h10-14,17,19,21-22,29,32H,15-16H2,1-9H3/b13-11+,14-12+,18-10+/t19-,21+,22-,29+/m0/s1
• InChIKey: UZHDGDDPOPDJGM-UBAANNQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3S,4R,5S,6S,7E,9E,11E)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methyl-4H-chromen-4-one
• IUPAC Traditional name: 2-[(3S,4R,5S,6S,7E,9E,11E)-4,6-dimethoxy-3,5,11-trimethyltrideca-7,9,11-trien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methylchromen-4-one
• Synonyms: 2-[(3S,4S,5S,6S,7E,9E,11E)-4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrien-1-yl]-8-hydroxy-5,7-dimethoxy-3-methyl-4H-1-Benzopyran-4-one; 2-[(3S,4S,5S,6S,7E,9E,11E)-4,6-dimethoxy-3,5,11-trimethyl-7,9,11-tridecatrienyl]-8-hydroxy-5,7-dimethoxy-3-methyl-4H-1-benzopyran-4-one; Stigmatellin A

Database IDs

• CAS Number: 94234-27-2
• PubChem SID: 164233791
• PubChem CID: 49867661

CALCULATED PROPERTIES

• Acid pKa: 9.058063
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 5.6586766
• LogD (pH = 7.4): 5.6494274
• Log P: 5.658796
• Molar Refractivity: 150.6702 cm^3
• Polarizability: 56.904724 Å^3
• Polar Surface Area: 83.45 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S686780

Stigmatellin A is an antibiotic. Stigmatellin A acts as an aromatic myxobacterial electron transport inhibitor. Stigmatellin A can be isolated from cells of the gliding bacterium S. aurantiaca strain Sga15.

REFERENCES

• Hoefle, G. et al.: Lieb. Annal. Chem., 12, 1993 (1984)
• Gaitatzis, N. et al.: J. Biol. Chem., 277, 13082 (1984)