Showing metabocard for D-Arginine (BMDB0003416)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:04:26 UTC
Update Date2020-05-21 16:28:31 UTC
BMDB IDBMDB0003416
Secondary Accession Numbers
  • BMDB03416
Metabolite Identification
Common NameD-Arginine
DescriptionD-Arginine, also known as D-arginine or DAR, belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-Arginine is possibly soluble (in water) and a very strong basic compound (based on its pKa). D-Arginine can be converted into 2-oxoarginine through its interaction with the enzyme D-amino-acid oxidase. In cattle, D-argininee is involved in the metabolic pathway called the D-argininee and D-ornithine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2-Amino-5-(carbamimidamido)pentanoic acidChEBI
(2R)-2-Amino-5-guanidinopentanoic acidChEBI
(R)-2-Amino-5-guanidinopentanoic acidChEBI
D-2-Amino-5-guanidinovaleric acidChEBI
D-ArgininChEBI
DARChEBI
(2R)-2-Amino-5-(carbamimidamido)pentanoateGenerator
(2R)-2-Amino-5-guanidinopentanoateGenerator
(R)-2-Amino-5-guanidinopentanoateGenerator
D-2-Amino-5-guanidinovalerateGenerator
Chemical FormulaC6H14N4O2
Average Molecular Weight174.201
Monoisotopic Molecular Weight174.111675712
IUPAC Name(2R)-2-amino-5-carbamimidamidopentanoic acid
Traditional NameD-arginine
CAS Registry Number157-06-2
SMILES
N[C@H](CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s1
InChI KeyODKSFYDXXFIFQN-SCSAIBSYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Peroxisome
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-3.5ALOGPS
logP-3.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)12.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.92 m³·mol⁻¹ChemAxon
Polarizability18.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen Locations
  • Epidermis
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003416
DrugBank IDDB04027
Phenol Explorer Compound IDNot Available
FooDB IDFDB023167
KNApSAcK IDNot Available
Chemspider ID64224
KEGG Compound IDC00792
BioCyc IDCPD-220
BiGG ID36012
Wikipedia LinkArginine
METLIN ID6924
PubChem Compound71070
PDB IDNot Available
ChEBI ID15816
References
Synthesis ReferenceBirnbaum, Sanford M.; Winitz, Milton; Greenstein, Jesse P. A simplified preparation of D-arginine. Archives of Biochemistry and Biophysics (1956), 60 496-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. D-aspartate oxidase
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
DDO
Uniprot ID:
P31228
Molecular weight:
37660.0
Reactions
D-Arginine + Water + Oxygen → 2-Oxoarginine + Ammonia + Hydrogen peroxidedetails