(4S,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: 160649
• Molecular Formular: C22H22Cl2N2O7
• Molecular Mass: 497.32528
• Monoisotopic Mass: 496.08040641
• SMILES: c12c(c(c3c(c1C)c(ccc3O)Cl)O)C(=O)[C@]1([C@@H](C2)[C@@H](C(=C(C1=O)C(=O)N)O)N(C)C)O.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-DTTSPEASSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,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: (4S,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: (4S,4aS,12aS)-7-Chloro-4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide Hydrochloride; Anhydroaureomycin Hydrochloride; Anhydrochlortetracycline Hydrochloride; Anhydrochlortetracyline Hydrochloride; [4S-(4α,4aα,12aα)]-7-Chloro-4-(dimethylamino)-1,4,4a,5,12,12a-hexahydro-3,10,11,12a-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide Hydrochloride; Anhydro Chlortetracycline Hydrochloride

Database IDs

• CAS Number: 65490-24-6
• PubChem SID: 162254784
• PubChem CID: 54710411

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; Methanol
• Apperance: Orange Solid
• Melting Point: >208°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A637740

Anhydrochlortetracycline is the anhydro analogue and impurity of Chlortetracycline (C426500). Anhydrochlortetracycline is an antimicrobial and antibacterial.

REFERENCES

• Diana, J. et al.: J. Pharmac. Biomed. Anal., 39, 523 (2005)
• Sanniez, W.H.K. et al.: J. Pharmac. Sci., 69, 5 (2005)
• Oliva, B. et al.: Antimircob. Agents Chemother., 36, 913 (2005)