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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:03 UTC
HMDB IDHMDB0000670
Secondary Accession Numbers
  • HMDB00670
Metabolite Identification
Common NameHomo-L-arginine
DescriptionL-homoarginine, also known as N6-(aminoiminomethyl)-L-lysine or N6-amidino-L-lysine, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. More specifically, L-homoarginine is a naturally occurring, non-proteinogenic, cationic amino acid. It is formed in the liver in a reaction catalyzed by L-arginine:glycine amidinotransferase (AGAT) when transferring the amidino group from arginine to lysine. It is an alternative substrate for nitric oxide (NO) synthase. L-homoarginine increases the availability of NO and thereby affects endothelial function. High homoarginine levels may exert positive actions that are relevant to cardiovascular health, including enhanced endothelial function, inhibition of platelet aggregation and stimulation of insulin secretion (PMID: 30866658 ). Recent studies have demonstrated that low serum homoarginine levels are a strong predictor of cardiovascular mortality (PMID: 24583919 ). L-homoarginine is a substrate of the human cationic amino acid CAT1 [solute carrier family 7 (SLC7A1)], CAT2A (SLC7A2A) or CAT2B (SLC7A2B) (PMID: 28684763 ). According to published human metabolomic data, L-homoarginine can be found primarily in blood, cerebrospinal fluid (CSF), and urine, as well as in human intestinal and testes tissues. Moreover, L-homoarginine has been found to be associated with liver cirrhosis and the genetic disorder, hyperargininemia. Homoarginine is an organ-specific uncompetitive inhibitor of human liver and bone alkaline phosphohydrolase (PMID: 5063678 ).
Structure
Thumb
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point213 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility363900 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Intestine
  • Placenta
  • Testis
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.65 +/- 0.70 uMAdult (>18 years old)BothCirrhosis details
Cerebrospinal Fluid (CSF)Detected and Quantified1.16 uMAdult (>18 years old)BothHyperargininemia details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C: Guanidino compounds in serum and urine of cirrhotic patients. Metabolism. 1995 May;44(5):584-8. [PubMed:7752905 ]
Hyperargininemia
  1. Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [PubMed:3433275 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000212
Good Scents IDrw1346121
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

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets. Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
Gene Name:
NOS3
Uniprot ID:
P29474
Molecular weight:
133273.59
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]