3,5-bis[(3S)-3-amino-3-carboxypropyl]-2-[(4S)-4-amino-4-carboxybutyl]-1-[(5S)-5-amino-5-carboxypentyl]pyridin-1-ium chloride

• ChemBase ID: 153585
• Molecular Formular: C24H40ClN5O8
• Molecular Mass: 562.0561
• Monoisotopic Mass: 561.25654095
• SMILES: c1c(c[n+](c(c1CC[C@@H](C(=O)O)N)CCC[C@@H](C(=O)O)N)CCCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N.[Cl-]
• Canonical SMILES: N[C@H](C(=O)O)CCCC[n+]1cc(CC[C@@H](C(=O)O)N)cc(c1CCC[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N.[Cl-]
• InChI: InChI=1S/C24H39N5O8.ClH/c25-16(21(30)31)4-1-2-11-29-13-14(7-9-18(27)23(34)35)12-15(8-10-19(28)24(36)37)20(29)6-3-5-17(26)22(32)33;/h12-13,16-19H,1-11,25-28H2,(H3-,30,31,32,33,34,35,36,37);1H/t16-,17-,18-,19-;/m0./s1
• InChIKey: QPBMCXWKTFGHKA-CHZBJCAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-bis[(3S)-3-amino-3-carboxypropyl]-2-[(4S)-4-amino-4-carboxybutyl]-1-[(5S)-5-amino-5-carboxypentyl]pyridin-1-ium chloride
• IUPAC Traditional name: 3,5-bis[(3S)-3-amino-3-carboxypropyl]-2-[(4S)-4-amino-4-carboxybutyl]-1-[(5S)-5-amino-5-carboxypentyl]pyridin-1-ium chloride
• Synonyms: Isodesmosine chloride; 2-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridinium Chloride; Isodesmosine Chloride

Database IDs

• CAS Number: 10059-18-4
• PubChem SID: 162247724
• PubChem CID: 71311683

CALCULATED PROPERTIES

• Acid pKa: 1.0397295
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -13.82377
• LogD (pH = 7.4): -13.83577
• Log P: -13.8239565
• Molar Refractivity: 133.3518 cm^3
• Polarizability: 52.80266 Å^3
• Polar Surface Area: 257.16 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Pale Yellow Thick Oil

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• 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: 99.5%±0.2%
• Biological Source: from bovine neck ligament
• Empirical Formula (Hill Notation): C24H40ClN5O8

DETAILS

Sigma Aldrich - I8404

Caution
Extremely hygroscopic, should be stored over silica gel
Preparation Note
Each vial contains 1μmole of purified isodesmosine isolated by solvent extraction and chromatography by method of Starcher et al, and calibrated by UV and amino acid analysis

Toronto Research Chemicals - I815050

A component of elastin. Isodesmosine is extremely hygroscopic and must be stored over a desiccant such as silica gel.

REFERENCES

• Partridge, S., et al.: Nature, 209, 399 (1966)