3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-[(5S)-5-amino-5-carboxy(1,1-2H2)pentyl](2H2)pyridin-1-ium

• ChemBase ID: 166631
• Molecular Formular: C24H40N5O8+
• Molecular Mass: 526.6031
• Monoisotopic Mass: 526.28768827
• SMILES: c1(c(c(c[n+](c1)CCCC[C@H](N)C(=O)O)CC[C@H](N)C(=O)O)CCC[C@H](N)C(=O)O)CC[C@H](N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)CCc1c[n+](CCCC[C@@H](C(=O)O)N)cc(c1CCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C24H39N5O8/c25-17(21(30)31)5-1-2-11-29-12-14(7-9-19(27)23(34)35)16(4-3-6-18(26)22(32)33)15(13-29)8-10-20(28)24(36)37/h12-13,17-20H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37)/p+1/t17-,18-,19-,20-/m0/s1
• InChIKey: VEVRNHHLCPGNDU-MUGJNUQGSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-[(5S)-5-amino-5-carboxy(1,1-^2H₂)pentyl](^2H₂)pyridin-1-ium
• IUPAC Traditional name: 3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-[(5S)-5-amino-5-carboxy(1,1-^2H₂)pentyl](^2H₂)pyridin-1-ium
• Synonyms: 4-[(4S)-4-Amino-4-carboxybutyl]-1-[(5S)-5-amino-5-carboxypentyl]-3,5-bis[(3S)-3-amino-3-carboxypropyl]pyridinium-d4; Desmosine-d4

Database IDs

• CAS Number: 1119270-58-4
• PubChem SID: 162260764
• PubChem CID: 71315805

CALCULATED PROPERTIES

• Acid pKa: 1.0354433
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -13.231828
• LogD (pH = 7.4): -13.243819
• Log P: -13.23201
• Molar Refractivity: 133.5261 cm^3
• Polarizability: 52.886124 Å^3
• Polar Surface Area: 257.16 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D296847

Labelled Desmosine. A component of elastin. It can be measured in all body fluids as biomarkers for in vivo degradation of matrix tissue elastin in man and animals.

REFERENCES

• Sato, F., et al.: Clin. Biochem., 39, 746 (2006)
• Koenders, M., et al.: J. Pathol., 218, 446 (2006)
• Ma, S. et al.: J. Chrom. Anal. Tech. Biomed. Life Sci., 879, 1893 (2006)