Cannabis Compound Database: Showing Compound Card for Arginine (CDB000117)

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Record Information

Version

1.0

Created at

2020-03-18 23:25:25 UTC

Updated at

2022-12-13 23:36:24 UTC

CannabisDB ID

CDB000117

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Arginine

Description

Arginine is an essential amino acid that is physiologically active in the L-form. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. Arginine can be considered to be a basic amino acid as the part of the side chain nearest to the backbone is long, carbon-containing, and hydrophobic, whereas the end of the side chain is a complex guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is used to make compounds such as nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. In large doses, L-arginine also stimulates the release of the hormones growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502 ¬†). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355 ¬†). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. The ratio of L-arginine to lysine is also important: soy and other plant proteins have more L-arginine than animal sources of protein. Arginine is one of the amino acids that are known in cannabis plant (PMID: 6991645 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Amino-5-(carbamimidamido)pentanoic acid	ChEBI
(2R)-2-Amino-5-guanidinopentanoic acid	ChEBI
(R)-2-Amino-5-guanidinopentanoic acid	ChEBI
D-2-Amino-5-guanidinovaleric acid	ChEBI
D-Arginin	ChEBI
DAR	ChEBI
(2R)-2-Amino-5-(carbamimidamido)pentanoate	Generator
(2R)-2-Amino-5-guanidinopentanoate	Generator
(R)-2-Amino-5-guanidinopentanoate	Generator
D-2-Amino-5-guanidinovalerate	Generator

Chemical Formula

C₆H₁₄N₄O₂

Average Molecular Weight

174.2

Monoisotopic Molecular Weight

174.1117

IUPAC Name

(2R)-2-amino-5-carbamimidamidopentanoic acid

Traditional Name

D-arginine

CAS Registry Number

157-06-2

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 Key

ODKSFYDXXFIFQN-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

D-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 Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:15816 )
arginine (CHEBI:15816 )
Other amino acids (C00792 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Tissue and substructures:

Epidermis

Cell and elements:

Element:

Platelet

Biofluid and excreta:

Blood

Subcellular:

Peroxisome

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	260 °C	Wikipedia
Boiling Point	368 °C	Wikipedia
Water Solubility	14.87 g/100 mL at 20 °C	Wikipedia
logP	0.0	Wikipedia

Predicted Properties

Property	Value	Source
logP	-3.5	ALOGPS
logP	-3.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.41	ChemAxon
pKa (Strongest Basic)	12.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	125.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.92 m³·mol⁻¹	ChemAxon
Polarizability	18.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9100000000-60db59de76b9a9b5bfc8	Spectrum
Predicted GC-MS	Arginine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9510000000-a5f3be057956f5efb0fd	Spectrum
Predicted GC-MS	Arginine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-1900000000-a1207a353a5d383e8118	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-38faac95afc81e981a08	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-776b9e0f6bf6a0ddf5ba	2012-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-0627028bdd33e89ac545	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03mi-8900000000-d00d08306af5359ec3dc	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-09fdbc63550a3fe95638	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-2900000000-4f23a56d70e700301134	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-7900000000-02e7df28226010832ffe	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-435f29993f2aaceb0d44	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0900000000-fe2cccae6934dad0053b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9200000000-da3c09ec6a806e5c0777	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-15e9d13a1d44b86b2a6c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-a706f1985fb3e9e0adbb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900000000-b42c24606ae24000888d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
D-Arginine and D-Ornithine Metabolism

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
D-amino-acid oxidase	DAO	12q24	P14920	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	7.909 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	4.771 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	6.114 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	4.578 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	3.474 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	4.651 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0003416

DrugBank ID

DB04027

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023167

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15816

References

General References

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 ]
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 ]
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 ]

Enzymes

Enzyme Details

1. D-amino-acid oxidase

General function:: Involved in D-amino-acid oxidase activity
Specific function:: Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:: DAO
Uniprot ID:: P14920
Molecular weight:: 39473.75

Showing Compound Card for Arginine (CDB000117)

Structure for CDB000117 (Arginine)

Enzymes