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Record Information
Version1.0
Created at2020-04-17 18:42:49 UTC
Updated at2020-12-07 19:11:05 UTC
CannabisDB IDCDB004846
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Arginine
Description
Structure
Thumb
Synonyms
Chemical FormulaC6H14N4O2
Average Molecular Weight174.2
Monoisotopic Molecular Weight174.1117
IUPAC Name(2S)-2-amino-5-carbamimidamidopentanoic acid
Traditional NameL-arginine
CAS Registry Number74-79-3
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-/m0/s1
InChI KeyODKSFYDXXFIFQN-BYPYZUCNSA-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
  • 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point222 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility182 mg/mL at 25 °CHuman Metabolome Project
logP-4.20HANSCH,C ET AL. (1995)
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
Polarizability17.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Y+L amino acid transporter 1SLC7A714q11.2Q9UM01 details
High affinity cationic amino acid transporter 1SLC7A113q12-q14P30825 details
Y+L amino acid transporter 2SLC7A616q22.1Q92536 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Arginase-1ARG16q23P05089 details
Protein-arginine deiminase type-4PADI41p36.13Q9UM07 details
Protein-arginine deiminase type-3PADI31p36.13Q9ULW8 details
NAD-dependent protein deacetylase sirtuin-6SIRT619p13.3Q8N6T7 details
Nitric oxide synthase, inducibleNOS217q11.2-q12P35228 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Nitric oxide synthase, endothelialNOS37q36P29474 details
Arginase-2, mitochondrialARG214q24.1P78540 details
Carnosine synthase 1CARNS111q13.2A5YM72 details
NOS1 mutantNOS112q24.2-q24.31B3VK56 details
[Protein ADP-ribosylarginine] hydrolaseADPRH3q13.31-q13.33P54922 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Protein-arginine deiminase type-4PADI41p36.13Q9UM07 details
NAD-dependent protein deacetylase sirtuin-6SIRT619p13.3Q8N6T7 details
Nitric oxide synthase, brainNOS112q24.2-q24.31P29475 details
Concentrations Data
Not Available
HMDB IDHMDB0000517
DrugBank IDDB00125
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002257
KNApSAcK IDC00001340
Chemspider ID6082
KEGG Compound IDC00062
BioCyc IDARG
BiGG ID33707
Wikipedia LinkL-arginine
METLIN ID5502
PubChem Compound6322
PDB IDNot Available
ChEBI ID16467
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Bauchart-Thevret C, Cui L, Wu G, Burrin DG: Arginine-induced stimulation of protein synthesis and survival in IPEC-J2 cells is mediated by mTOR but not nitric oxide. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E899-909. doi: 10.1152/ajpendo.00068.2010. Epub 2010 Sep 14. [PubMed:20841502 ]
  3. Linden KC, Wadley GD, Garnham AP, McConell GK: Effect of l-arginine infusion on glucose disposal during exercise in humans. Med Sci Sports Exerc. 2011 Sep;43(9):1626-34. doi: 10.1249/MSS.0b013e318212a317. [PubMed:21311355 ]
  4. Vega-Lopez S, Matthan NR, Ausman LM, Harding SV, Rideout TC, Ai M, Otokozawa S, Freed A, Kuvin JT, Jones PJ, Schaefer EJ, Lichtenstein AH: Altering dietary lysine:arginine ratio has little effect on cardiovascular risk factors and vascular reactivity in moderately hypercholesterolemic adults. Atherosclerosis. 2010 Jun;210(2):555-62. doi: 10.1016/j.atherosclerosis.2009.12.002. Epub 2009 Dec 5. [PubMed:20042191 ]

Only showing the first 10 proteins. There are 41 proteins in total.

Enzymes

General function:
Involved in arginase activity
Specific function:
Not Available
Gene Name:
ARG1
Uniprot ID:
P05089
Molecular weight:
34734.655
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development. May be involved in the response to heart failure by elevating local creatine synthesis.
Gene Name:
GATM
Uniprot ID:
P50440
Molecular weight:
48455.01
General function:
Involved in nucleotide binding
Specific function:
Forms part of a macromolecular complex that catalyzes the attachment of specific amino acids to cognate tRNAs during protein synthesis. Modulates the secretion of AIMP1 and may be involved in generation of the inflammatory cytokine EMAP2 from AIMP1.
Gene Name:
RARS
Uniprot ID:
P54136
Molecular weight:
75378.295
General function:
Involved in argininosuccinate synthase activity
Specific function:
Not Available
Gene Name:
ASS1
Uniprot ID:
P00966
Molecular weight:
46530.055
General function:
Involved in protein-arginine deiminase activity
Specific function:
Catalyzes the citrullination/deimination of arginine residues of proteins. Citrullinates histone H3 at 'Arg-8' and/or 'Arg-17' and histone H4 at 'Arg-3', which prevents their methylation by CARM1 and HRMT1L2/PRMT1 and represses transcription. Citrullinates EP300/P300 at 'Arg-2142', which favors its interaction with NCOA2/GRIP1.
Gene Name:
PADI4
Uniprot ID:
Q9UM07
Molecular weight:
74078.65
General function:
Involved in protein-arginine deiminase activity
Specific function:
Catalyzes the deimination of arginine residues of proteins.
Gene Name:
PADI3
Uniprot ID:
Q9ULW8
Molecular weight:
74742.705
General function:
Involved in argininosuccinate lyase activity
Specific function:
Not Available
Gene Name:
ASL
Uniprot ID:
P04424
Molecular weight:
51657.505
General function:
Involved in zinc ion binding
Specific function:
NAD-dependent protein deacetylase. Has deacetylase activity towards histone H3K9Ac and H3K56Ac. Modulates acetylation of histone H3 in telomeric chromatin during the S-phase of the cell cycle. Deacetylates histone H3K9Ac at NF-kappa-B target promoters and may down-regulate the expression of a subset of NF-kappa-B target genes. Acts as a corepressor of the transcription factor HIF1A to control the expression of multiple glycolytic genes to regulate glucose homeostasis. Required for genomic stability. Regulates the production of TNF protein. Has a role in the regulation of life span (By similarity). Deacetylation of nucleosomes interferes with RELA binding to target DNA. May be required for the association of WRN with telomeres during S-phase and for normal telomere maintenance. Required for genomic stability. Required for normal IGF1 serum levels and normal glucose homeostasis. Modulates cellular senescence and apoptosis. On DNA damage, promotes DNA end resection via deacetylation of RBBP8. Has very weak deacetylase activity and can bind NAD(+) in the absence of acetylated substrate.
Gene Name:
SIRT6
Uniprot ID:
Q8N6T7
Molecular weight:
36064.295
General function:
Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
Specific function:
Not Available
Gene Name:
ART3
Uniprot ID:
Q13508
Molecular weight:
43922.97
General function:
Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
Specific function:
Not Available
Gene Name:
ART5
Uniprot ID:
Q96L15
Molecular weight:
32053.48

Transporters

General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
General function:
Involved in transport
Specific function:
Involved in the sodium-independent uptake of dibasic amino acids and sodium-dependent uptake of some neutral amino acids. Requires co-expression with SLC3A2/4F2hc to mediate the uptake of arginine, leucine and glutamine. Plays a role in nitric oxide synthesis in human umbilical vein endothelial cells (HUVECs) via transport of L-arginine. Involved in the transport of L- arginine in monocytes
Gene Name:
SLC7A7
Uniprot ID:
Q9UM01
Molecular weight:
55990.0
General function:
Involved in transport
Specific function:
High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor
Gene Name:
SLC7A1
Uniprot ID:
P30825
Molecular weight:
67637.6
General function:
Involved in transport
Specific function:
Involved in the sodium-independent uptake of dibasic amino acids and sodium-dependent uptake of some neutral amino acids. Requires co-expression with SLC3A2/4F2hc to mediate the uptake of arginine, leucine and glutamine. Also acts as an arginine/glutamine exchanger, following an antiport mechanism for amino acid transport, influencing arginine release in exchange for extracellular amino acids. Plays a role in nitric oxide synthesis in human umbilical vein endothelial cells (HUVECs) via transport of L-arginine. Involved in the transport of L-arginine in monocytes. Reduces uptake of ornithine in retinal pigment epithelial (RPE) cells
Gene Name:
SLC7A6
Uniprot ID:
Q92536
Molecular weight:
56826.9

Only showing the first 10 proteins. There are 41 proteins in total.