D-Arginine

Identification

Name
D-Arginine
Accession Number
DB04027  (EXPT01113)
Type
Small Molecule
Groups
Experimental
Description

A D-α-amino acid that is the D-isomer of arginine (only the L-form is physiologically active).

Structure
Thumb
Synonyms
  • (2R)-2-amino-5-(carbamimidamido)pentanoic acid
  • (2R)-2-amino-5-guanidinopentanoic acid
  • (R)-2-amino-5-guanidinopentanoic acid
  • D-2-Amino-5-guanidinovaleric acid
  • D-Arginin
Categories
Not Available
UNII
R54Z304Z7C
CAS number
157-06-2
Weight
Average: 174.201
Monoisotopic: 174.111675712
Chemical Formula
C6H14N4O2
InChI Key
ODKSFYDXXFIFQN-SCSAIBSYSA-N
InChI
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
IUPAC Name
(2R)-2-amino-5-carbamimidamidopentanoic acid
SMILES
N[[email protected]](CCCNC(N)=N)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCreatine kinase M-typeNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Kyriakos Makryaleas, Karlheinz Drauz, Andreas Bommarius, "Method for the preparation of D-arginine and L-ornithine." U.S. Patent US5591613, issued April, 1995.

US5591613
General References
Not Available
External Links
Human Metabolome Database
HMDB03416
KEGG Compound
C00792
ChemSpider
64224
ChEBI
15816
ChEMBL
CHEMBL212301
HET
DAR
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.28 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.92 m3·mol-1ChemAxon
Polarizability18.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7047
Blood Brain Barrier+0.6875
Caco-2 permeable-0.7139
P-glycoprotein substrateNon-substrate0.5629
P-glycoprotein inhibitor INon-inhibitor0.988
P-glycoprotein inhibitor IINon-inhibitor0.8802
Renal organic cation transporterNon-inhibitor0.7663
CYP450 2C9 substrateNon-substrate0.7822
CYP450 2D6 substrateNon-substrate0.6948
CYP450 3A4 substrateNon-substrate0.8044
CYP450 1A2 substrateNon-inhibitor0.8491
CYP450 2C9 inhibitorNon-inhibitor0.8966
CYP450 2D6 inhibitorNon-inhibitor0.9172
CYP450 2C19 inhibitorNon-inhibitor0.7693
CYP450 3A4 inhibitorNon-inhibitor0.9192
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9951
Ames testAMES toxic0.7057
CarcinogenicityNon-carcinogens0.9254
BiodegradationReady biodegradable0.9466
Rat acute toxicity1.6259 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9446
hERG inhibition (predictor II)Non-inhibitor0.9652
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-1900000000-a1207a353a5d383e8118
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-38faac95afc81e981a08
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00di-9000000000-776b9e0f6bf6a0ddf5ba
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of chemical entities known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organic acids and derivatives
Sub Class
Carboxylic acids and derivatives
Direct Parent
D-alpha-amino acids
Alternative Parents
Fatty acids and conjugates / Guanidines / Amino acids / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
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
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-alpha-amino acid, arginine (CHEBI:15816 ) / Other amino acids (C00792 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Creatine kinase activity
Specific Function
Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with l...
Gene Name
CKM
Uniprot ID
P06732
Uniprot Name
Creatine kinase M-type
Molecular Weight
43100.91 Da
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 ]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:30