(2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid

• ChemBase ID: 3820
• Molecular Formular: C11H20N2O6
• Molecular Mass: 276.2863
• Monoisotopic Mass: 276.13213637
• SMILES: N[C@@H](CCCCN[C@@H](CCC(=O)O)C(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)NCCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1
• InChIKey: ZDGJAHTZVHVLOT-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid
• IUPAC Traditional name: saccharopine
• Synonyms: N-(5-Amino-5-Carboxypentyl)Glutamic Acid; ε-N-(L-glutar-2-yl)-L-lysine; N6-(L-1,3-dicarboxylpropyl)-L-lysine; L-Saccharopine

Database IDs

• CAS Number: 997-68-2
• MDL Number: MFCD00056743
• PubChem SID: 160967257; 46505056; 24899487
• PubChem CID: 160556

CALCULATED PROPERTIES

ALOGPS 2.1

• Solubility (Water): 5.25e+00 g/l
• Log P: -2.77
• LOG S: -1.72

JChem

• Acid pKa: 1.4444536
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -6.389692
• LogD (pH = 7.4): -8.158041
• Log P: -5.4074354
• Molar Refractivity: 63.953 cm^3
• Polarizability: 25.778957 Å^3
• Polar Surface Area: 149.95 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

DrugBank - DB04207

Drug information: experimental

Sigma Aldrich - S1634

Preparation Note
Prepared enzymatically
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. S1634.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.