(2S,4S)-1-(2H-1,3-benzodioxol-5-ylmethyl)-4-{N-[(3-methoxyphenyl)methyl]-3,3-dimethylbutanamido}pyrrolidine-2-carboxylic acid

• ChemBase ID: 161244
• Molecular Formular: C27H34N2O6
• Molecular Mass: 482.56866
• Monoisotopic Mass: 482.24168682
• SMILES: C1[C@H](N(C[C@H]1N(C(=O)CC(C)(C)C)Cc1cccc(c1)OC)Cc1ccc2c(c1)OCO2)C(=O)O
• Canonical SMILES: COc1cccc(c1)CN(C(=O)CC(C)(C)C)[C@H]1C[C@H](N(C1)Cc1ccc2c(c1)OCO2)C(=O)O
• InChI: InChI=1S/C27H34N2O6/c1-27(2,3)13-25(30)29(15-18-6-5-7-21(10-18)33-4)20-12-22(26(31)32)28(16-20)14-19-8-9-23-24(11-19)35-17-34-23/h5-11,20,22H,12-17H2,1-4H3,(H,31,32)/t20-,22-/m0/s1
• InChIKey: QCZCVUBJYKQGOQ-UNMCSNQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-1-(2H-1,3-benzodioxol-5-ylmethyl)-4-{N-[(3-methoxyphenyl)methyl]-3,3-dimethylbutanamido}pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,4S)-1-(2H-1,3-benzodioxol-5-ylmethyl)-4-{N-[(3-methoxyphenyl)methyl]-3,3-dimethylbutanamido}pyrrolidine-2-carboxylic acid
• Synonyms: (4S)-1-(1,3-Benzodioxol-5-ylmethyl)-4-[(3,3-dimethyl-1-oxobutyl)[(3-methoxyphenyl)methyl]amino]-L-proline

Database IDs

• CAS Number: 334999-53-0
• PubChem SID: 162255379
• PubChem CID: 20578929

CALCULATED PROPERTIES

• Acid pKa: 1.2599314
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.99743676
• LogD (pH = 7.4): 0.9513674
• Log P: 0.99782455
• Molar Refractivity: 130.3818 cm^3
• Polarizability: 51.371685 Å^3
• Polar Surface Area: 88.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: CD3OD; CDCl3
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B200010

Intermediate in the preparation and formulation of proline derivatives for pharmaceutical and cosmetic uses as mediators of hedgehog signaling pathways.