Showing metabocard for Desmosine (BMDB0000572)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:32:59 UTC
Update Date2020-05-11 20:12:35 UTC
BMDB IDBMDB0000572
Secondary Accession Numbers
  • BMDB00572
Metabolite Identification
Common NameDesmosine
DescriptionDesmosine belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Desmosine is a very strong basic compound (based on its pKa).
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 Weight526.6031
Monoisotopic Molecular Weight526.287688281
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
CAS Registry Number11003-57-9
SMILES
NC(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 Identifier
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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Epidermis
  • Kidney
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000572
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000516
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesmosine
METLIN ID5554
PubChem Compound53477704
PDB IDNot Available
ChEBI ID37628
References
Synthesis ReferenceRencher, 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
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available