(1aS,1bS,5S,5aR,7aR)-5-({[4-(4-carboxybutanamido)phenyl]carbamoyl}methyl)-1b,7a-dimethyl-decahydrooxireno[2,3-f]quinolin-5-ium-5-olate

• ChemBase ID: 5515
• Molecular Formular: C24H33N3O6
• Molecular Mass: 459.53532
• Monoisotopic Mass: 459.23693579
• SMILES: O=C(O)CCCC(=O)Nc1ccc(cc1)NC(=O)C[N@+]1(CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@H]2O1)[O-]
• Canonical SMILES: O=C(C[N@@+]1([O-])CCC[C@]2([C@H]1CC[C@@]1([C@H]2O1)C)C)Nc1ccc(cc1)NC(=O)CCCC(=O)O
• InChI: InChI=1S/C24H33N3O6/c1-23-12-4-14-27(32,18(23)11-13-24(2)22(23)33-24)15-20(29)26-17-9-7-16(8-10-17)25-19(28)5-3-6-21(30)31/h7-10,18,22H,3-6,11-15H2,1-2H3,(H,25,28)(H,26,29)(H,30,31)/t18-,22+,23+,24-,27+/m1/s1
• InChIKey: VFIZFTGABDUGCF-UPVHCHBVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1aS,1bS,5S,5aR,7aR)-5-({[4-(4-carboxybutanamido)phenyl]carbamoyl}methyl)-1b,7a-dimethyl-decahydrooxireno[2,3-f]quinolin-5-ium-5-olate
• IUPAC Traditional name: (1aS,1bS,5S,5aR,7aR)-5-({[4-(4-carboxybutanamido)phenyl]carbamoyl}methyl)-1b,7a-dimethyl-hexahydro-1aH-oxireno[2,3-f]quinolin-5-ium-5-olate
• Synonyms: 4-{4-[2-(1A,7A-DIMETHYL-4-OXY-OCTAHYDRO-1-OXA-4-AZA-CYCLOPROPA[A]NAPHTHALEN-4-YL) -ACETYLAMINO]-PHENYLCARBAMOYL}-BUTYRIC ACID

Database IDs

• PubChem SID: 160968943; 99444353
• PubChem CID: 5288514

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.1076446
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.27139473
• LogD (pH = 7.4): -1.9590598
• Log P: 1.1350669
• Molar Refractivity: 123.5106 cm^3
• Polarizability: 46.632442 Å^3
• Polar Surface Area: 134.91 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.58
• LOG S: -4.67
• Solubility (Water): 9.89e-03 g/l

DETAILS

DrugBank - DB07882

Drug information: experimental