(1R,3S,4S,8S)-4,17-bis(dimethylamino)-5,8,14-trihydroxy-7-oxo-10,11-diazapentacyclo[10.7.1.03,8.09,20.013,18]icosa-5,9(20),11,13,15,17-hexaene-6-carboxamide

• ChemBase ID: 177128
• Molecular Formular: C23H27N5O5
• Molecular Mass: 453.49098
• Monoisotopic Mass: 453.20121899
• SMILES: c1cc(c2c(c1N(C)C)C[C@@H]1c3c2n[nH]c3[C@]2([C@@H](C1)[C@@H](C(=C(C2=O)C(=O)N)O)N(C)C)O)O
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@@H]1Cc3c(c4c1c2[nH]n4)c(O)ccc3N(C)C)O)O)C
• InChI: InChI=1S/C23H27N5O5/c1-27(2)12-5-6-13(29)15-10(12)7-9-8-11-18(28(3)4)19(30)16(22(24)32)21(31)23(11,33)20-14(9)17(15)25-26-20/h5-6,9,11,18,29-30,33H,7-8H2,1-4H3,(H2,24,32)(H,25,26)/t9-,11-,18-,23-/m0/s1
• InChIKey: MQKZTYSCFGLAOV-SNSZBMKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,4S,8S)-4,17-bis(dimethylamino)-5,8,14-trihydroxy-7-oxo-10,11-diazapentacyclo[10.7.1.0^3,^8.0^9,^2^0.0^1^3,^1^8]icosa-5,9(20),11,13,15,17-hexaene-6-carboxamide
• IUPAC Traditional name: (1R,3S,4S,8S)-4,17-bis(dimethylamino)-5,8,14-trihydroxy-7-oxo-10,11-diazapentacyclo[10.7.1.0^3,^8.0^9,^2^0.0^1^3,^1^8]icosa-5,9(20),11,13,15,17-hexaene-6-carboxamide
• Synonyms: [2bS-(2bα,6α,6aα,7aα)]-6,9-Bis(dimethylamino)-2,2b,3,6,6a,7,7a,8-octahydro-2b,5,12-trihydroxy-3-oxo-benzo[g]naphth[1,2,3-cd]indazole-4-carboxamide; Pyrazolo Minocycline

Database IDs

• CAS Number: 182004-72-4
• PubChem SID: 164233038
• PubChem CID: 54686081

CALCULATED PROPERTIES

• Acid pKa: 0.3517227
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.9065056
• LogD (pH = 7.4): -2.3511183
• Log P: -2.3658538
• Molar Refractivity: 123.9783 cm^3
• Polarizability: 47.10039 Å^3
• Polar Surface Area: 156.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P843500

A substituted tetracycline compound for the treatment of bacterial infections and neoplasms.

REFERENCES

• Weitzman, S.A., et al.: Science, 227, 1231 (1985)
• Cheeseman, K.H., et al.: Biochem. Pharmacol., 37, 4225 (1985)
• Canevari, L., Neurochem. Res., 29, 637 (1985)