(4R,4aS,12aS)-7-chloro-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide hydrochloride

• ChemBase ID: 168034
• Molecular Formular: C22H22Cl2N2O7
• Molecular Mass: 497.32528
• Monoisotopic Mass: 496.08040641
• SMILES: c1cc(c2c(c1O)c(c1c(c2C)C[C@@H]2[C@](C1=O)(C(=O)C(=C([C@@H]2N(C)C)O)C(=O)N)O)O)Cl.Cl
• Canonical SMILES: CN([C@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1Cc1c(C2=O)c(O)c2c(c1C)c(Cl)ccc2O)O)O)C.Cl
• InChI: InChI=1S/C22H21ClN2O7.ClH/c1-7-8-6-9-16(25(2)3)18(28)15(21(24)31)20(30)22(9,32)19(29)13(8)17(27)14-11(26)5-4-10(23)12(7)14;/h4-5,9,16,26-28,32H,6H2,1-3H3,(H2,24,31);1H/t9-,16+,22-;/m0./s1
• InChIKey: WIOSVFADOBZUQR-PXAZKYFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,4aS,12aS)-7-chloro-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydrotetracene-2-carboxamide hydrochloride
• IUPAC Traditional name: (4R,4aS,12aS)-7-chloro-4-(dimethylamino)-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-4a,5-dihydro-4H-tetracene-2-carboxamide hydrochloride
• Synonyms: [4R-(4α,4aβ,12aβ)]-7-Chloro-4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide Monohydrochloride; 4-Epianhydrochlortetracycline Hydrochloride

Database IDs

• CAS Number: 158018-53-2
• PubChem SID: 162262166
• PubChem CID: 54710413

CALCULATED PROPERTIES

• Acid pKa: -2.4525576
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.75771654
• LogD (pH = 7.4): -0.9736463
• Log P: -0.7556079
• Molar Refractivity: 117.1494 cm^3
• Polarizability: 45.421997 Å^3
• Polar Surface Area: 161.39 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Orange Solid
• Melting Point: >210°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - E578060

Modified Tetracycline analog

REFERENCES

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