Desmosine (CHEM021878)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:38 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021878
Identification
Common NameDesmosine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(4-Amino-4-carboxybutyl)-1-(5-amino-5-carboxypentyl)-3,5-bis(3-amino-3-carboxypropyl)pyridiniumHMDB
DesmosineMeSH
Chemical FormulaC24H40N5O8
Average Molecular Mass526.603 g/mol
Monoisotopic Mass526.288 g/mol
CAS Registry Number11003-57-9
IUPAC Name3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-(5-amino-5-carboxypentyl)pyridin-1-ium
Traditional Name3,5-bis[(3S)-3-amino-3-carboxypropyl]-4-[(4S)-4-amino-4-carboxybutyl]-1-(5-amino-5-carboxypentyl)pyridin-1-ium
SMILESNC(CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1)C(O)=O
InChI IdentifierInChI=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
InChI KeyVEVRNHHLCPGNDU-NIVVRJPPSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTetracarboxylic acids and derivatives
Direct ParentTetracarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tetracarboxylic acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Aralkylamine
  • Pyridine
  • Pyridinium
  • Heteroaromatic compound
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP-4.5ALOGPS
logP-13ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)1.04ChemAxon
pKa (Strongest Basic)10.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area257.16 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity133.53 m³·mol⁻¹ChemAxon
Polarizability56.4 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-0000900000-64c725d85f44d0ade63aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05g0-8100098000-49762d050753246255e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000190000-760a274d2ce59871397cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0097-0000920000-e995b52b9c9010ed39e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0i01-2100900000-bc52bbe1e56f6c011adcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-d1853206aef8d4c91afbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1000090000-b59aa402259987bdbb50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9200320000-e8dc575b5c38c51817b8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000572
FooDB IDFDB000516
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5554
PDB IDNot Available
Wikipedia LinkDesmosine
Chemspider IDNot Available
ChEBI ID37628
PubChem Compound ID53477704
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Rencher, William Franklin, Jr. Design and synthesis of desmosine-like peptidyl carbamates as novel inhibitors of human leukocyte elastase. (1988), 164 pp. CAN 111:233627 AN 1989:633627
2. Luisetti M, Sturani C, Sella D, Madonini E, Galavotti V, Bruno G, Peona V, Kucich U, Dagnino G, Rosenbloom J, Starcher B, Grassi C: MR889, a neutrophil elastase inhibitor, in patients with chronic obstructive pulmonary disease: a double-blind, randomized, placebo-controlled clinical trial. Eur Respir J. 1996 Jul;9(7):1482-6.
3. Ono S, Yamauchi M: Elastin cross-linking in the skin from patients with amyotrophic lateral sclerosis. J Neurol Neurosurg Psychiatry. 1994 Jan;57(1):94-6.
4. Uitto J, Santa Cruz DJ, Starcher BC, Whyte MP, Murphy WA: Biochemical and ultrastructural demonstration of elastin accumulation in the skin lesions of the Buschke-Ollendorff syndrome. J Invest Dermatol. 1981 Apr;76(4):284-7.
5. Tenholder MF, Rajagopal KR, Phillips YY, Dillard TA, Bennett LL, Mundie TG, Tellis CJ: Urinary desmosine excretion as a marker of lung injury in the adult respiratory distress syndrome. Chest. 1991 Nov;100(5):1385-90.
6. Fill JA, Brandt JT, Wiedemann HP, Rinehart BL, Lindemann CF, Komara JJ, Bowsher RR, Spence MC, Zeiher BG: Urinary desmosine as a biomarker in acute lung injury. Biomarkers. 2006 Jan-Feb;11(1):85-96.
7. Viglio S, Iadarola P, Lupi A, Trisolini R, Tinelli C, Balbi B, Grassi V, Worlitzsch D, Doring G, Meloni F, Meyer KC, Dowson L, Hill SL, Stockley RA, Luisetti M: MEKC of desmosine and isodesmosine in urine of chronic destructive lung disease patients. Eur Respir J. 2000 Jun;15(6):1039-45.
8. Ma S, Lieberman S, Turino GM, Lin YY: The detection and quantitation of free desmosine and isodesmosine in human urine and their peptide-bound forms in sputum. Proc Natl Acad Sci U S A. 2003 Oct 28;100(22):12941-3. Epub 2003 Oct 16.
9. Oikarinen AI, Palatsi R, Adomian GE, Oikarinen H, Clark JG, Uitto J: Anetoderma: biochemical and ultrastructural demonstration of an elastin defect in the skin of three patients. J Am Acad Dermatol. 1984 Jul;11(1):64-72.
10. Wondrak GT, Roberts MJ, Jacobson MK, Jacobson EL: 3-hydroxypyridine chromophores are endogenous sensitizers of photooxidative stress in human skin cells. J Biol Chem. 2004 Jul 16;279(29):30009-20. Epub 2004 May 7.
11. Pasquali-Ronchetti I, Baccarani-Contri M: Elastic fiber during development and aging. Microsc Res Tech. 1997 Aug 15;38(4):428-35.
12. Viglio S, Annovazzi L, Luisetti M, Stolk J, Casado B, Iadarola P: Progress in the methodological strategies for the detection in real samples of desmosine and isodesmosine, two biological markers of elastin degradation. J Sep Sci. 2007 Feb;30(2):202-13.
13. Cantor JO, Shteyngart B: How a test for elastic fiber breakdown products in sputum could speed development of a treatment for pulmonary emphysema. Med Sci Monit. 2004 Jan;10(1):RA1-4.
14. Stone PJ: Potential use of collagen and elastin degradation markers for monitoring liver fibrosis in schistosomiasis. Acta Trop. 2000 Oct 23;77(1):97-9.