4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(5R)-5-amino-5-carboxylatopentyl]-5-hydroxypyridin-1-ium

• ChemBase ID: 166003
• Molecular Formular: C18H28N4O7
• Molecular Mass: 412.43752
• Monoisotopic Mass: 412.19579926
• SMILES: c1(c(c(c[n+](c1)CCCC[C@@H](N)C(=O)[O-])O)C[C@H](N)C(=O)O)CC[C@H](N)C(=O)O
• Canonical SMILES: N[C@@H](C(=O)[O-])CCCC[n+]1cc(O)c(c(c1)CC[C@@H](C(=O)O)N)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C18H28N4O7/c19-12(16(24)25)3-1-2-6-22-8-10(4-5-13(20)17(26)27)11(15(23)9-22)7-14(21)18(28)29/h8-9,12-14H,1-7,19-21H2,(H3-,23,24,25,26,27,28,29)/t12-,13+,14+/m1/s1
• InChIKey: ZAHDXEIQWWLQQL-RDBSUJKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(5R)-5-amino-5-carboxylatopentyl]-5-hydroxypyridin-1-ium
• IUPAC Traditional name: 4-[(2S)-2-amino-2-carboxyethyl]-3-[(3S)-3-amino-3-carboxypropyl]-1-[(5R)-5-amino-5-carboxylatopentyl]-5-hydroxypyridin-1-ium
• Synonyms: 4-[(2S)-2-Amino-2-carboxyethyl]-1-[(5S)-5-amino-5-carboxypentyl]-3-[(3S)-3-amino-3-carboxypropyl]-5-hydroxypyridinium Inner Salt; Lysylpyridinoline; Deoxypyridinoline

Database IDs

• CAS Number: 83462-55-9
• PubChem SID: 162260136
• PubChem CID: 105071

CALCULATED PROPERTIES

• Acid pKa: 0.8331798
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -11.7394705
• LogD (pH = 7.4): -12.480978
• Log P: -11.7144
• Molar Refractivity: 113.4828 cm^3
• Polarizability: 40.298786 Å^3
• Polar Surface Area: 216.9 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D249900

A colagen cross-links agent.

REFERENCES

• Heaney, R., et al.: J. Bone Miner. Res., 5, 1135 (1990)
• Hannon, R., et al.: J. Bone Miner. Res., 13, 1124 (1990)
• Coudray, C., et al.: Eur. J. Nutr., 42, 91 (1990)
• Abrams, S., et al.: Am. J. Clin. Nutr., 82, 471 (1990)