ChemFOnt: Showing chemical card for D-Arginine (CFc000001877)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:37 UTC

Chemfont ID

CFc000001877

Molecule Identification

Common Name

D-Arginine

Definition

D-Arginine, also known as D-2-amino-5-guanidinovaleric acid or (2R)-2-amino-5-guanidinopentanoate, is a member of the class of compounds known as D-alpha-amino acids. D-alpha-Amino acids are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-Arginine is slightly soluble (in water). D-Arginine can be found in human epidermis and platelet tissues. Within the cell, D-arginine is primarily located in the peroxisome. In humans, D-arginine is involved in D-arginine and D-ornithine metabolism. Arginine (abbreviated as Arg or R) is an alpha-amino acid that is used in the biosynthesis of proteins. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG. It contains an alpha-amino group, an alpha-carboxylic acid group, and a side chain consisting of a 3-carbon aliphatic straight chain ending in a guanidino group. At physiological pH, the carboxylic acid is deprotonated, the amino group is protonated, and the guanidino group is also protonated to give the guanidinium form (-C-(NH2)2+), making arginine a charged, aliphatic amino acid. It is the precursor for the biosynthesis of nitric oxide. D-Arginine is an essential amino acid that is physiologically active in the L-form.

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

174.201

Monoisotopic Molecular Weight

174.111675712

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 )

Functional Ontology

Not Available

Epidermis (HMDB: HMDB0003416)

Cell

Hematocyte

Platelet (HMDB: HMDB0003416)

Cellular substructure

Organelle

Peroxisome (HMDB: HMDB0003416)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0003416)

Source

Exogenous

Exogenous (HMDB: HMDB0003416)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0003416)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

D-Arginine and D-Ornithine Metabolism (HMDB: HMDB0003416)
D-Arginine and D-Ornithine Metabolism (PathBank: SMP0087291)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003416)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.28 g/L	ALOGPS
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

External Links

HMDB ID

HMDB0003416

DrugBank ID

DB04027

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Birnbaum, Sanford M.; Winitz, Milton; Greenstein, Jesse P. A simplified preparation of D-arginine. Archives of Biochemistry and Biophysics (1956), 60 496-8.

Showing chemical card for D-Arginine (CFc000001877)

MOL for CFc000001877 (D-Arginine)

3D MOL for CFc000001877 (D-Arginine)

3D SDF for CFc000001877 (D-Arginine)

3D-SDF for CFc000001877 (D-Arginine)

PDB for CFc000001877 (D-Arginine)

3D PDB for CFc000001877 (D-Arginine)

SMILES for CFc000001877 (D-Arginine)

INCHI for CFc000001877 (D-Arginine)

Structure for CFc000001877 (D-Arginine)

3D Structure for CFc000001877 (D-Arginine)