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

• ChemBase ID: 178265
• Molecular Formular: C22H24N2O8
• Molecular Mass: 444.43456
• Monoisotopic Mass: 444.15326574
• SMILES: c1cc(c2c(c1)[C@]([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)C)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@@]1(C)O)cccc2O)O)O)C
• InChI: InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15+,21+,22-/m0/s1
• InChIKey: OFVLGDICTFRJMM-PMXORCKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,4aS,5aS,6S,12aS)-4-[bis(^2H₃)methylamino]-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
• IUPAC Traditional name: (4R,4aS,5aS,6S,12aS)-4-[bis(^2H₃)methylamino]-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
• Synonyms: (4R,4aS,5aS,6S,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide-d6; Quatrimycin-d6; [4R-(4α,4aβ,5aβ,6α,12aβ)]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide-d6; 4-epi-Tetracycline-d6 (approximately 50% pure, contains unidentified salts)

Database IDs

• PubChem SID: 164234175
• PubChem CID: 57369181

CALCULATED PROPERTIES

• Acid pKa: -2.2437224
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.3970165
• LogD (pH = 7.4): -6.222226
• Log P: -3.5476153
• Molar Refractivity: 114.1883 cm^3
• Polarizability: 43.205765 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Dark Yellow Solid
• Melting Point: >207°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - T291407

Labelled metabolite of Tetracycline (T291400)

REFERENCES

• Diana, J., et al.: J. Pharm. Biomed. Anal., 39, 523 (2005)
• Fritz, J., et al.: Food Chem., 105, 1297 (2005)
• Gratacos-Cubarsi, M., et al.: J. Agric. Food Chem., 55, 4610 (2005)