(4R,4aS,5aR,12aS)-4-[bis(2H3)methylamino]-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

• ChemBase ID: 177689
• Molecular Formular: C21H22N2O7
• Molecular Mass: 414.40858
• Monoisotopic Mass: 414.14270105
• SMILES: c1ccc(c2c1C[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
• Canonical SMILES: CN([C@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@@H]1Cc3cccc(c3C(=O)C1=C2O)O)O)O)C
• InChI: InChI=1S/C21H22N2O7/c1-23(2)15-10-7-9-6-8-4-3-5-11(24)12(8)16(25)13(9)18(27)21(10,30)19(28)14(17(15)26)20(22)29/h3-5,9-10,15,24,26-27,30H,6-7H2,1-2H3,(H2,22,29)/t9-,10-,15+,21-/m0/s1
• InChIKey: XDVCLKFLRAWGIT-QJBAFNDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,4aS,5aR,12aS)-4-[bis(^2H₃)methylamino]-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4R,4aS,5aR,12aS)-4-[bis(^2H₃)methylamino]-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• Synonyms: (4R,4aS,5aR,12aS)-4-(Dimethyl-d6-amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide Hydrochloride; 6-Demethyl-6-deoxyepitetracycline-d6 Hydrochloride; epi-Sancycline-d6 Hydrochloride

Database IDs

• PubChem SID: 164233599
• PubChem CID: 57347509

CALCULATED PROPERTIES

• Acid pKa: -2.1955726
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -3.444874
• LogD (pH = 7.4): -5.268215
• Log P: -2.6734078
• Molar Refractivity: 108.1116 cm^3
• Polarizability: 40.642216 Å^3
• Polar Surface Area: 161.39 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S111507

The labelled 4-epimer of Sancycline. A semi-synthetic antibiotic related to Tetracycline.

REFERENCES

• Gozalbes, R., et al.: J. Pharm. Pharmacol., 51, 111 (1999)
• Estrada, E., et al.: J. Med. Chem., 43, 1975 (1999)
• Gonzalez, H., et al.: J. Mol. Mod., 8, 237 (1999)