(2S,3S)-2,3-dihydroxybutanedioic acid; N-{[(2S)-1-butylpyrrolidin-2-yl]methyl}-4-cyano-1-methoxynaphthalene-2-carboxamide

• ChemBase ID: 153180
• Molecular Formular: C26H33N3O8
• Molecular Mass: 515.55552
• Monoisotopic Mass: 515.22676503
• SMILES: CCCCN1CCC[C@H]1CNC(=O)c1cc(c2ccccc2c1OC)C#N.[C@H]([C@@H](C(=O)O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)O)O.CCCCN1CCC[C@H]1CNC(=O)c1cc(C#N)c2c(c1OC)cccc2
• InChI: InChI=1S/C22H27N3O2.C4H6O6/c1-3-4-11-25-12-7-8-17(25)15-24-22(26)20-13-16(14-23)18-9-5-6-10-19(18)21(20)27-2;5-1(3(7)8)2(6)4(9)10/h5-6,9-10,13,17H,3-4,7-8,11-12,15H2,1-2H3,(H,24,26);1-2,5-6H,(H,7,8)(H,9,10)/t17-;1-,2-/m00/s1
• InChIKey: WOPHJTZRFZTRKU-FJMPKIMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-dihydroxybutanedioic acid; N-{[(2S)-1-butylpyrrolidin-2-yl]methyl}-4-cyano-1-methoxynaphthalene-2-carboxamide
• IUPAC Traditional name: D-tartaric acid; N-{[(2S)-1-butylpyrrolidin-2-yl]methyl}-4-cyano-1-methoxynaphthalene-2-carboxamide
• Synonyms: (-)-N[n-Butyl-2-pyrrolidinyl)methyl]-1-methoxy-4-cyanonaphthalene-2-carboxamide tartrate; 2-Naphthalenecarboxamide tartrate; (S)-Nafadotride tartrate

Database IDs

• CAS Number: 173429-65-7
• MDL Number: MFCD05664733
• PubChem SID: 24724548; 162247319
• PubChem CID: 16078989

CALCULATED PROPERTIES

• Polarizability: 42.412125 Å^3
• Polar Surface Area: 65.36 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false
• Acid pKa: 13.702464
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.3900635
• LogD (pH = 7.4): 2.0228946
• Log P: 3.543572
• Molar Refractivity: 107.772 cm^3

PROPERTIES

Physical Property

• Solubility: H2O: soluble ~9 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C26H33O8N3

DETAILS

Sigma Aldrich - N3535

Biochem/physiol Actions
D3 Dopamine receptor antagonist.