(4R,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

• ChemBase ID: 165731
• Molecular Formular: C21H21ClN2O8
• Molecular Mass: 464.85304
• Monoisotopic Mass: 464.09864332
• 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
• 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
• InChI: InChI=1S/C21H21ClN2O8/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)/t6-,7-,14+,15-,21-/m0/s1
• InChIKey: FMTDIUIBLCQGJB-PTACOPLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4R,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• Synonyms: [4R-(4α,4aβ,5aβ,6α,12aβ)]-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide; 4-Epidemeclocycline; 4-Epidemethylchlortetracycline; 4-epi-Demeclocycline (~90%)

Database IDs

• CAS Number: 14206-59-8
• PubChem SID: 162259864
• PubChem CID: 54731359

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

PROPERTIES

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D230730

A Tetracycline analog as gelatinase inhibitor with known efficacy, safety, and side effects; used for the treatment of diseases such as rheumatoid arthritis and multiple sclerosis.

REFERENCES

• Paemen, L., et al.: Biochem. Pharmacol., 52, 105 (1996)