Canavanine

Identification

Generic Name
Canavanine
DrugBank Accession Number
DB01833
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 176.1738
Monoisotopic: 176.09094027
Chemical Formula
C5H12N4O3
Synonyms
  • (L)-Canavanine
  • 2-Amino-4-(guanidinooxy)butyric acid
  • Canavanin
  • L-Canavanine
  • O-((Aminoiminomethyl)amino)-L-homoserine

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, endothelialNot 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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-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
L-alpha-amino acids
Alternative Parents
Fatty acids and conjugates / Guanidines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Fatty acid / Guanidine / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid (CHEBI:609827)
Affected organisms
Not Available

Chemical Identifiers

UNII
3HZV514J4B
CAS number
543-38-4
InChI Key
FSBIGDSBMBYOPN-VKHMYHEASA-N
InChI
InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1
IUPAC Name
(2S)-2-amino-4-(carbamimidamidooxy)butanoic acid
SMILES
N[C@@H](CCONC(N)=N)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0002706
KEGG Compound
C00308
PubChem Compound
439202
PubChem Substance
46507101
ChemSpider
388342
BindingDB
50370459
ChEBI
609827
ChEMBL
CHEMBL443732
ZINC
ZINC000003869452
PDBe Ligand
GGB
Wikipedia
Canavanine
PDB Entries
3lap / 3u88 / 4m2f / 4q2x / 4y4g / 5n3k / 5rpd / 5uti / 6cba / 6nse
show 6 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
logP-3.7Chemaxon
pKa (Strongest Acidic)2.1Chemaxon
pKa (Strongest Basic)10.34Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area134.45 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity61.24 m3·mol-1Chemaxon
Polarizability17.02 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6949
Blood Brain Barrier+0.776
Caco-2 permeable-0.6707
P-glycoprotein substrateNon-substrate0.6462
P-glycoprotein inhibitor INon-inhibitor0.9281
P-glycoprotein inhibitor IINon-inhibitor0.9795
Renal organic cation transporterNon-inhibitor0.8358
CYP450 2C9 substrateNon-substrate0.8185
CYP450 2D6 substrateNon-substrate0.7847
CYP450 3A4 substrateNon-substrate0.7424
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.909
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9033
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9785
Ames testAMES toxic0.7585
CarcinogenicityNon-carcinogens0.9017
BiodegradationReady biodegradable0.7581
Rat acute toxicity2.1576 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.947
hERG inhibition (predictor II)Non-inhibitor0.9137
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
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0uk9-2930000000-f0b7791e84a9692c9896
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9100000000-97acb154cb1e58dea04a
GC-MS Spectrum - GC-MSGC-MSsplash10-0uk9-2930000000-f0b7791e84a9692c9896
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-1bb8236fdf1b58516604
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-01b9-4900000000-bb3b6e4a69d652b8ca9f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-06di-9400000000-d5093b67a7ae4861da94
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4i-9100000000-c152969360d44d895d0f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0k96-9000000000-277b39712e9095e29987
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-004i-0900000000-ba76dc7ddbe1f642142a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-004i-7900000000-e4399ab6ff268986734e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00b9-9100000000-fa6508b89d97cec98552
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-05di-9000000000-3dadb3257235bbed4b41
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0ab9-9000000000-c1e347b18ad0b5e0667e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-1bb8236fdf1b58516604
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-01b9-4900000000-6273e4c764e53645e523
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-06di-9400000000-d5093b67a7ae4861da94
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9100000000-c152969360d44d895d0f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0k96-9000000000-277b39712e9095e29987
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-0900000000-ba76dc7ddbe1f642142a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-7900000000-e4399ab6ff268986734e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00b9-9100000000-e6d11248bff03dbe3f4e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05di-9000000000-444161e8e39f43477d96
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ab9-9000000000-c1e347b18ad0b5e0667e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9100000000-ba2ea26f650023acc7b7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-b48f86c738a7fadfd8e8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-37a47df8029ab6c03477
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05gi-9500000000-2ee0154a1ffa85a7f8fb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-dbc79cba9e9e1cd440ee
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-9100000000-069f1fc9b9ca23fcf295
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]-143.1375723
predicted
DarkChem Lite v0.1.0
[M-H]-143.0612723
predicted
DarkChem Lite v0.1.0
[M-H]-131.7595
predicted
DeepCCS 1.0 (2019)
[M+H]+144.2490723
predicted
DarkChem Lite v0.1.0
[M+H]+144.4963723
predicted
DarkChem Lite v0.1.0
[M+H]+135.58687
predicted
DeepCCS 1.0 (2019)
[M+Na]+143.3391723
predicted
DarkChem Lite v0.1.0
[M+Na]+143.5840723
predicted
DarkChem Lite v0.1.0
[M+Na]+144.934
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
Molecular Weight
133287.62 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