(2S)-N-[(2E,4E,6S,7S)-7-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(1E,3E,5E)-7-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trien-1-yl]oxolan-2-yl]-6-methoxy-5-methylocta-2,4-dien-1-yl]-2-[(2S,3R,4R,6S)-2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3E)-penta-1,3-dien-1-yl]oxan-2-yl]butanamide

• ChemBase ID: 3745
• Molecular Formular: C44H62N2O12
• Molecular Mass: 810.96928
• Monoisotopic Mass: 810.43027543
• SMILES: CC[C@H](C(=O)NC/C=C/C=C(\C)/[C@@H](OC)[C@H](C)[C@@H]1O[C@@H](/C=C/C=C/C=C(\C)/C(=O)c2c(O)ccn(C)c2=O)[C@H](O)[C@H]1O)[C@]1(O)O[C@@H](/C=C/C=C/C)C(C)(C)[C@@H](O)[C@H]1O
• Canonical SMILES: C/C=C/C=C/[C@@H]1O[C@@](O)([C@@H](C(=O)NC/C=C/C=C(/[C@H]([C@@H]([C@@H]2O[C@H]([C@@H]([C@H]2O)O)/C=C/C=C/C=C(/C(=O)c2c(O)ccn(c2=O)C)\C)C)OC)\C)CC)[C@@H]([C@@H](C1(C)C)O)O
• InChI: InChI=1S/C44H62N2O12/c1-10-12-14-22-32-43(6,7)39(51)40(52)44(55,58-32)29(11-2)41(53)45-24-18-17-20-27(4)37(56-9)28(5)38-36(50)35(49)31(57-38)21-16-13-15-19-26(3)34(48)33-30(47)23-25-46(8)42(33)54/h10,12-23,25,28-29,31-32,35-40,47,49-52,55H,11,24H2,1-9H3,(H,45,53)/b12-10+,15-13+,18-17+,21-16+,22-14+,26-19+,27-20+/t28-,29+,31-,32-,35-,36+,37+,38-,39-,40+,44-/m0/s1
• InChIKey: NTAHMPNXQOYXSX-UFLBAAKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2E,4E,6S,7S)-7-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(1E,3E,5E)-7-(4-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-3-yl)-6-methyl-7-oxohepta-1,3,5-trien-1-yl]oxolan-2-yl]-6-methoxy-5-methylocta-2,4-dien-1-yl]-2-[(2S,3R,4R,6S)-2,3,4-trihydroxy-5,5-dimethyl-6-[(1E,3E)-penta-1,3-dien-1-yl]oxan-2-yl]butanamide
• IUPAC Traditional name: aurodox
• Synonyms: Antibiotic X-5108; Goldinodox; Goldinomycin; 1-Methylmocimycin; Aurodox

Database IDs

• CAS Number: 12704-90-4
• PubChem SID: 46506336; 160967183
• PubChem CID: 46936896; 54715136

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.026206
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): 2.0132227
• LogD (pH = 7.4): 0.35345685
• Log P: 3.4975646
• Molar Refractivity: 227.7773 cm^3
• Polarizability: 85.74541 Å^3
• Polar Surface Area: 215.55 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.23
• LOG S: -5.07
• Solubility (Water): 6.98e-03 g/l

DETAILS

DrugBank - DB04124

• Drug Groups: experimental
• Description: Aurodox is an antibiotic obtained from a streptomyces variant considered as possibly effective against streptococcus pyogenes infections. It may promote growth in poultry.