D-arginine
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Overview
- DrugBank ID
- DB04027
- Type
- Small Molecule
- 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
Target Actions Organism UCreatine kinase M-type Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- Human Metabolome Database
- HMDB0003416
- KEGG Compound
- C00792
- PubChem Compound
- 71070
- PubChem Substance
- 46506552
- ChemSpider
- 64224
- 1742746
- ChEBI
- 15816
- ChEMBL
- CHEMBL212301
- ZINC
- ZINC000001532749
- PDBe Ligand
- DAR
- Wikipedia
- Arginine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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
Property Value Source Water Solubility 2.28 mg/mL 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 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7047 Blood Brain Barrier + 0.6875 Caco-2 permeable - 0.7139 P-glycoprotein substrate Non-substrate 0.5629 P-glycoprotein inhibitor I Non-inhibitor 0.988 P-glycoprotein inhibitor II Non-inhibitor 0.8802 Renal organic cation transporter Non-inhibitor 0.7663 CYP450 2C9 substrate Non-substrate 0.7822 CYP450 2D6 substrate Non-substrate 0.6948 CYP450 3A4 substrate Non-substrate 0.8044 CYP450 1A2 substrate Non-inhibitor 0.8491 CYP450 2C9 inhibitor Non-inhibitor 0.8966 CYP450 2D6 inhibitor Non-inhibitor 0.9172 CYP450 2C19 inhibitor Non-inhibitor 0.7693 CYP450 3A4 inhibitor Non-inhibitor 0.9192 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9951 Ames test AMES toxic 0.7057 Carcinogenicity Non-carcinogens 0.9254 Biodegradation Ready biodegradable 0.9466 Rat acute toxicity 1.6259 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9446 hERG inhibition (predictor II) Non-inhibitor 0.9652
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 146.5785786 predictedDarkChem Lite v0.1.0 [M-H]- 146.2003786 predictedDarkChem Lite v0.1.0 [M-H]- 131.91443 predictedDeepCCS 1.0 (2019) [M+H]+ 147.3967786 predictedDarkChem Lite v0.1.0 [M+H]+ 147.3800786 predictedDarkChem Lite v0.1.0 [M+H]+ 135.74178 predictedDeepCCS 1.0 (2019) [M+Na]+ 147.2865786 predictedDarkChem Lite v0.1.0 [M+Na]+ 147.0860786 predictedDarkChem Lite v0.1.0 [M+Na]+ 145.12718 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsCreatine kinase M-type
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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