D-arginine

Overview

DrugBank ID
DB04027
Type
Small Molecule
US Approved
NO
Other Approved
NO
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
D-arginine
DrugBank Accession Number
DB04027
Background

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

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 174.201
Monoisotopic: 174.111675712
Chemical Formula
C6H14N4O2
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

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCreatine kinase M-typeNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
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
Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboximidamide / Carboxylic acid / D-alpha-amino acid / Fatty acid / Guanidine / Hydrocarbon derivative
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-alpha-amino acid, arginine (CHEBI:15816) / Other amino acids (C00792)
Affected organisms
Not Available

Chemical Identifiers

UNII
R54Z304Z7C
CAS number
157-06-2
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[C@H](CCCNC(N)=N)C(O)=O

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
Human Metabolome Database
HMDB0003416
KEGG Compound
C00792
PubChem Compound
71070
PubChem Substance
46506552
ChemSpider
64224
RxNav
1742746
ChEBI
15816
ChEMBL
CHEMBL212301
ZINC
ZINC000001532749
PDBe Ligand
DAR
Wikipedia
Arginine

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

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-MSsplash10-00dl-9100000000-60db59de76b9a9b5bfc8
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/MSsplash10-004i-1900000000-ab2b5c2c40bbf6b9b264
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-0c4db4147486764cd124
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9200000000-0d21425420fe93d3eec8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-3b258f818397aa914cea
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-1be596e4a8b74335ff90
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-faa3c67873c43e76f2ee
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-146.5785786
predicted
DarkChem Lite v0.1.0
[M-H]-146.2003786
predicted
DarkChem Lite v0.1.0
[M-H]-131.91443
predicted
DeepCCS 1.0 (2019)
[M+H]+147.3967786
predicted
DarkChem Lite v0.1.0
[M+H]+147.3800786
predicted
DarkChem Lite v0.1.0
[M+H]+135.74178
predicted
DeepCCS 1.0 (2019)
[M+Na]+147.2865786
predicted
DarkChem Lite v0.1.0
[M+Na]+147.0860786
predicted
DarkChem Lite v0.1.0
[M+Na]+145.12718
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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 large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa
Specific Function
ATP binding
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52