(4S,4aR,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride

• ChemBase ID: 172802
• Molecular Formular: C22H23ClN2O8
• Molecular Mass: 478.87962
• Monoisotopic Mass: 478.11429339
• SMILES: c1cc(c2c(c1)C(=C)[C@@H]1C(=C([C@]3([C@@H](C1O)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O)C2=O)O.Cl
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C(O)[C@@H]1C(=C)c3cccc(c3C(=O)C1=C2O)O)O)O)C.Cl
• InChI: InChI=1S/C22H22N2O8.ClH/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31);1H/t10-,14-,15+,17?,22+;/m1./s1
• InChIKey: VZQARNDJLLWXGL-SRABGVDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aR,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride
• IUPAC Traditional name: (4S,4aR,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide hydrochloride
• Synonyms: Londomycin; Metacycline Hydrochloride; Metadomus; Metilenbiotic; Optimycin; Physiomycine; Rindex; Methacycline Hydrochloride; (4S,4aR,5S,5aR,12aS)-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide Hydrochloride; Adriamicina; Ciclobiotic; Germiciclin

Database IDs

• CAS Number: 3963-95-9
• PubChem SID: 164228712
• PubChem CID: 71750023

CALCULATED PROPERTIES

• Acid pKa: -2.2804315
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.5773673
• LogD (pH = 7.4): -6.4795337
• Log P: -3.6468134
• Molar Refractivity: 113.6694 cm^3
• Polarizability: 43.031315 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M258785

Broad spectrum, semisynthetic antibiotic related to Tetracycline. Antibacterial.

REFERENCES

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Chodosh, S., et al.: Chest, 69, 587 (1971)