(4S,4aS,5aS,6S,12aS)-4-[bis(2H3)methylamino]-7-chloro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride

• ChemBase ID: 165730
• Molecular Formular: C21H22Cl2N2O8
• Molecular Mass: 501.31398
• Monoisotopic Mass: 500.07532103
• SMILES: c1cc(c2c(c1Cl)[C@H]([C@@H]1C(=C([C@]3([C@@H](C1)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)C2=O)O)O.Cl
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@H]1C(=C2O)C(=O)c2c([C@H]1O)c(Cl)ccc2O)O)O)C.Cl
• InChI: InChI=1S/C21H21ClN2O8.ClH/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31;/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31);1H/t6-,7-,14-,15-,21-;/m0./s1
• InChIKey: GVSJQNRGSCOSNJ-KBHRXELFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aS,6S,12aS)-4-[bis(^2H₃)methylamino]-7-chloro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride
• IUPAC Traditional name: (4S,4aS,5aS,6S,12aS)-4-[bis(^2H₃)methylamino]-7-chloro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide hydrochloride
• Synonyms: [4S-(4α,4aα,5aα,6β,12aα)]-7-Chloro-4-(dimethyl-d6)amino-d3-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide Monohydrochloride; 6-Demethyl-7-chlorotetracycline-d6 Hydrochloride; Demetraciclina-d6; Detravis-d6; Ledermycin-d6 Hydrochloride; Meciclin-d6; Demeclocycline-d6 HydrochlorideDiscontinued

Database IDs

• PubChem SID: 162259863
• PubChem CID: 71315365

CALCULATED PROPERTIES

• Acid pKa: -2.5592184
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.3682384
• LogD (pH = 7.4): -6.1644874
• Log P: -3.2341983
• Molar Refractivity: 114.3549 cm^3
• Polarizability: 43.324028 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D230727

Labelled Demeclocycline (D230725). An antibiotic related to tetracycline and produced by streptomyces aureofaciens. Because it is excreted more slowly than tetracycline, it maintains effective blood levels for longer periods of time.

REFERENCES

• Jilka, R., et al.: J. Clin. Invest., 104, 439 (1999)
• Hauge, E; Bone, 28, 556 (1999)
• Dobnig, H., et al.: J. Clin. Endocrinol. Metab., 90, 3970 (1999)