(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-8-(2-oxopropyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 168951
• Molecular Formular: C28H31NO10
• Molecular Mass: 541.54644
• Monoisotopic Mass: 541.1947962
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(c2c(c1O)C[C@@](C[C@@H]2O[C@H]1C[C@H]([C@@H]([C@@H](O1)C)O)N)(O)CC(=O)C)O)OC
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)CC(=O)C
• InChI: InChI=1S/C28H31NO10/c1-11(30)8-28(36)9-14-20(17(10-28)39-18-7-15(29)23(31)12(2)38-18)27(35)22-21(25(14)33)24(32)13-5-4-6-16(37-3)19(13)26(22)34/h4-6,12,15,17-18,23,31,33,35-36H,7-10,29H2,1-3H3/t12-,15-,17-,18-,23+,28-/m0/s1
• InChIKey: GKOUBQUQZFFVPW-BJRCHLRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-8-(2-oxopropyl)-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-8-(2-oxopropyl)-9,10-dihydro-7H-tetracene-5,12-dione
• Synonyms: (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-8-(2-oxopropyl)-5,12-naphthacenedione; 8S-cis)-10-[(3-Amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-8-(2-oxopropyl)-5,12-naphthacenedione; Feudomycin B

Database IDs

• CAS Number: 79438-97-4
• PubChem SID: 162263083
• PubChem CID: 10053050

CALCULATED PROPERTIES

• Acid pKa: 9.532358
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.6930556
• LogD (pH = 7.4): 0.47402346
• Log P: 1.6669817
• Molar Refractivity: 137.4407 cm^3
• Polarizability: 53.852222 Å^3
• Polar Surface Area: 185.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F321800

Feudomycin B is an anthracycline metabolite produced via Streptomyces biosynthesis.

REFERENCES

• Oki, T. et al.: J. Antibiot., 34, 783 (1981)
• Hautala, A. et al.: J. Antibiot., 56, 143 (1981)