(1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

• ChemBase ID: 1312
• Molecular Formular: C9H15NO3
• Molecular Mass: 185.2203
• Monoisotopic Mass: 185.10519335
• SMILES: O[C@@H]1[C@@H]([C@@H]2N([C@@H](CC2)C1)C)C(=O)O
• Canonical SMILES: O[C@H]1C[C@@H]2CC[C@H]([C@H]1C(=O)O)N2C
• InChI: InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5-,6+,7-,8+/m0/s1
• InChIKey: PHMBVCPLDPDESM-FKSUSPILSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• IUPAC Traditional name: ecgonine; @ecgonine
• Synonyms: Ecgonine

Database IDs

• CAS Number: 481-37-8
• PubChem SID: 160964772; 46506479
• PubChem CID: 91460
• Chemspider ID: 82586
• DrugBank ID: DB01525
• Wikipedia Title: Ecgonine

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4801822
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.0927565
• LogD (pH = 7.4): -3.0912147
• Log P: -3.0901585
• Molar Refractivity: 46.5693 cm^3
• Polarizability: 18.560587 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.69
• LOG S: 0.75
• Solubility (Water): 1.05e+03 g/l

PROPERTIES

Physical Property

• Solubility: 178 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Melting Point: 198–199 °C
• Density: 1.293 ± 0.06 g·cm^−3

DETAILS

DrugBank - DB01525

• Drug Groups: illicit; experimental
• External Links: Wikipedia