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

• ChemBase ID: 164712
• Molecular Formular: C22H24Cl2N2O8
• Molecular Mass: 515.34056
• Monoisotopic Mass: 514.0909711
• SMILES: c1(ccc(c2c1[C@](C1C(=C([C@]3([C@@H](C1)[C@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)C2=O)(O)C)O)Cl.Cl
• Canonical SMILES: CN([C@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1CC1C(=C2O)C(=O)c2c([C@@]1(C)O)c(Cl)ccc2O)O)O)C.Cl
• InChI: InChI=1S/C22H23ClN2O8.ClH/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21;/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31);1H/t7?,8-,15+,21-,22-;/m0./s1
• InChIKey: CBHYYLPALVVVEY-FYRLHVCPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,4aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride
• IUPAC Traditional name: (4R,4aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide hydrochloride
• Synonyms: (4R,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide Monohydrate; 4-Epichlortetracycline Hydrochloride; 4-epi-Chlortetracycline Hydrochloride

Database IDs

• CAS Number: 101342-45-4
• PubChem SID: 162258847
• PubChem CID: 71314846

CALCULATED PROPERTIES

• Acid pKa: -2.5133889
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.0490828
• LogD (pH = 7.4): -5.852484
• Log P: -2.951973
• Molar Refractivity: 118.9931 cm^3
• Polarizability: 45.145546 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Pyridine
• Apperance: Pale Yellow Solid
• Melting Point: >180°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - C426501

A Tetracycline derivative. It is a metalloprotease inhibitor, used in treating tissue destructive diseases and cancer.

REFERENCES

• Golub, et al.: J. Periodont. Res., 20, 12 (1985)
• Maragoudakis, et al.: Br. J. Pharmacol., 111, 894 (1985)