6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid

• ChemBase ID: 172447
• Molecular Formular: C29H38N4O10
• Molecular Mass: 602.63282
• Monoisotopic Mass: 602.25879344
• SMILES: c1cc(c2c(c1)[C@]([C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)NCNCCCCC(N)C(=O)O)O)N(C)C)O)O)C2=O)(O)C)O
• Canonical SMILES: NC(C(=O)O)CCCCNCNC(=O)C1=C(O)[C@@H](N(C)C)[C@H]2[C@](C1=O)(O)C(=C1[C@H](C2)[C@](C)(O)c2c(C1=O)c(O)ccc2)O
• InChI: InChI=1S/C29H38N4O10/c1-28(42)13-7-6-9-17(34)18(13)22(35)19-14(28)11-15-21(33(2)3)23(36)20(25(38)29(15,43)24(19)37)26(39)32-12-31-10-5-4-8-16(30)27(40)41/h6-7,9,14-16,21,31,34,36-37,42-43H,4-5,8,10-12,30H2,1-3H3,(H,32,39)(H,40,41)/t14-,15-,16?,21-,28+,29-/m0/s1
• InChIKey: AHEVKYYGXVEWNO-UNKJSYSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid
• IUPAC Traditional name: 6-[({[(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracen-2-yl]formamido}methyl)amino]-2-aminohexanoic acid
• Synonyms: N6-[[[[(4S,4aS,5aS,6S,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenyl]carbonyl]amino]methyl]-L-lysine; Armyl; Ciclisin; Ciclolysal; Ciclolysine; Infaciclina; Lisinbiotic; Lisinciclina; Mucomycin; N-Lysinomethyltetracycline; Tetramyl; Lymecycline

Database IDs

• CAS Number: 992-21-2
• PubChem SID: 164228357
• PubChem CID: 54714462

CALCULATED PROPERTIES

• Acid pKa: 0.4019689
• H Acceptors: 13
• H Donor: 9
• LogD (pH = 5.5): -8.334031
• LogD (pH = 7.4): -8.35059
• Log P: -8.298649
• Molar Refractivity: 154.5096 cm^3
• Polarizability: 59.682735 Å^3
• Polar Surface Area: 242.98 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L487800

A semi-synthetic antibiotic related to Tetracycline (T291400). Antibacterial.

REFERENCES

• Andrews, C., et al.: Pharm. Res., 17, 639 (2000)
• Votano, J., et al.: J. Med. Chem., 49, 7169 (2000)
• Davis, A., et al.: Curr. Opin. Chem. Biol., 8, 378 (2000)