(1S,3aR,8aS)-5-{[(2-ethylphenyl)carbamoyl]oxy}-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-1-ium-1-olate

• ChemBase ID: 5479
• Molecular Formular: C22H27N3O3
• Molecular Mass: 381.46808
• Monoisotopic Mass: 381.20524174
• SMILES: c1(c(cccc1)CC)NC(=O)Oc1ccc2N(C)[C@@H]3[C@](c2c1)(C)CC[N@@+]3([O-])C
• Canonical SMILES: CCc1ccccc1NC(=O)Oc1ccc2c(c1)[C@@]1(C)CC[N@@+]([C@@H]1N2C)([O-])C
• InChI: InChI=1S/C22H27N3O3/c1-5-15-8-6-7-9-18(15)23-21(26)28-16-10-11-19-17(14-16)22(2)12-13-25(4,27)20(22)24(19)3/h6-11,14,20H,5,12-13H2,1-4H3,(H,23,26)/t20-,22+,25-/m0/s1
• InChIKey: MVHRCJQCKYPDRL-HOKHCIIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3aR,8aS)-5-{[(2-ethylphenyl)carbamoyl]oxy}-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-1-ium-1-olate
• IUPAC Traditional name: (1S,3aR,8aS)-5-{[(2-ethylphenyl)carbamoyl]oxy}-1,3a,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-1-ium-1-olate
• Synonyms: 1S,3AS,8AS-TRIMETHYL-1-OXIDO-1,2,3,3A,8,8A-HEXAHYDROPYRROLO[2,3-B]INDOL-5-YL 2-ETHYLPHENYLCARBAMATE

Database IDs

• PubChem SID: 160968907; 99444317
• PubChem CID: 46937098

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.904953
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.083716
• LogD (pH = 7.4): 4.083715
• Log P: 4.0837164
• Molar Refractivity: 111.6423 cm^3
• Polarizability: 41.460407 Å^3
• Polar Surface Area: 68.45 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.42
• LOG S: -4.62
• Solubility (Water): 9.08e-03 g/l

DETAILS

DrugBank - DB07846

Drug information: experimental