Showing metabocard for Homo-L-arginine (BMDB0000670)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:34:39 UTC
Update Date2021-01-12 22:02:00 UTC
BMDB IDBMDB0000670
Secondary Accession Numbers
  • BMDB00670
Metabolite Identification
Common NameHomo-L-arginine
DescriptionHomo-L-arginine, also known as n6-amidino-lysine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Homo-L-arginine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Homo-L-arginine exists in all living organisms, ranging from bacteria to humans. Homo-L-arginine is a potentially toxic compound. Homo-L-arginine has been found to be associated with the diseases known as cirrhosis; also homo-l-arginine has been linked to the inborn metabolic disorders including hyperargininemia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
HomoarginineChEBI
L-N(6)-AmidinolysineChEBI
N6-(Aminoiminomethyl)-L-lysineChEBI
N6-Amidino-L-lysineChEBI
N6-Amidino-lysineChEBI
L-HomoarginineKegg
Homo-L-arginineChEBI
Chemical FormulaC7H16N4O2
Average Molecular Weight188.2275
Monoisotopic Molecular Weight188.127325776
IUPAC Name(2S)-2-amino-6-carbamimidamidohexanoic acid
Traditional NameL-homoarginine
CAS Registry Number156-86-5
SMILES
N[C@@H](CCCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1
InChI KeyQUOGESRFPZDMMT-YFKPBYRVSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acid
  • Fatty acyl
  • Guanidine
  • Amino acid
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Imine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point213 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.7ALOGPS
logP-2.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)12.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.52 m³·mol⁻¹ChemAxon
Polarizability20.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Intestine
  • Milk
  • Placenta
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000670
DrugBank IDDB03974
Phenol Explorer Compound IDNot Available
FooDB IDFDB112164
KNApSAcK IDC00001364
Chemspider ID8732
KEGG Compound IDC01924
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5640
PubChem Compound9085
PDB IDNot Available
ChEBI ID27747
References
Synthesis ReferenceIzumiya, Nobuo. Synthesis of DL-homoarginine and Na-methyl-DL-homoarginine. Nippon Kagaku Zasshi (1951), 72 521-3. CODEN: NPKZAZ ISSN:0369-5387. CAN 46:42183 AN 1952:42183
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Karetnikova ES, Jarzebska N, Markov AG, Weiss N, Lentz SR, Rodionov RN: Is Homoarginine a Protective Cardiovascular Risk Factor? Arterioscler Thromb Vasc Biol. 2019 May;39(5):869-875. doi: 10.1161/ATVBAHA.118.312218. [PubMed:30866658 ]
  3. Sobczak A, Prokopowicz A, Radek M, Szula M, Zaciera M, Kurek J, Goniewicz ML: Tobacco smoking decreases plasma concentration of the emerging cardiovascular risk marker, L-homoarginine. Circ J. 2014;78(5):1254-8. doi: 10.1253/circj.cj-13-1334. Epub 2014 Feb 28. [PubMed:24583919 ]
  4. Chafai A, Fromm MF, Konig J, Maas R: The prognostic biomarker L-homoarginine is a substrate of the cationic amino acid transporters CAT1, CAT2A and CAT2B. Sci Rep. 2017 Jul 6;7(1):4767. doi: 10.1038/s41598-017-04965-2. [PubMed:28684763 ]
  5. Lin CW, Fishman WH: L-Homoarginine. An organ-specific, uncompetitive inhibitor of human liver and bone alkaline phosphohydrolases. J Biol Chem. 1972 May 25;247(10):3082-7. [PubMed:5063678 ]