NAV

Vinylglycine

Identification

Generic Name
Vinylglycine
DrugBank Accession Number
DB03214
Background

Vinylglycine is an irreversible inhibitor of aspartate aminotransferase.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 101.1039
Monoisotopic: 101.047678473
Chemical Formula
C4H7NO2
Synonyms
  • (2S)-2-amino-3-butenoic acid
  • L-vinylglycine
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UL-amino-acid oxidaseNot AvailableHumans
U1-aminocyclopropane-1-carboxylate synthase-like protein 1Not 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
Unsaturated fatty acids / 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 / Fatty acyl / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
LGD04MMJ5E
CAS number
70982-53-5
InChI Key
RQVLGLPAZTUBKX-VKHMYHEASA-N
InChI
InChI=1S/C4H7NO2/c1-2-3(5)4(6)7/h2-3H,1,5H2,(H,6,7)/t3-/m0/s1
IUPAC Name
(2S)-2-aminobut-3-enoic acid
SMILES
N[C@@H](C=C)C(O)=O

References

Synthesis Reference

DONALD J. ARMSTRONG, MARK D. AZEVEDO, KERRY L. MCPHAIL, MICHAEL D. JACKSON, DALLICE I. MILLS, GARY BANOWETZ, MURALIDHARA THIMMAIAH, ANNE B. HALGREN, "CONTROL OF GRASSY WEEDS WITH VINYLGLYCINES AND VINYLGLYCINE-PRODUCING ORGANISMS." U.S. Patent US20100093536, issued April 15, 2010.

US20100093536
General References
Not Available
PubChem Compound
156126
PubChem Substance
46506124
ChemSpider
137492
ChEBI
43858
ZINC
ZINC000001566185
PDBe Ligand
LVG
PDB Entries
1tdk

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
Water Solubility250.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-2.5Chemaxon
logS0.39ALOGPS
pKa (Strongest Acidic)2.42Chemaxon
pKa (Strongest Basic)8.95Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area63.32 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity24.91 m3·mol-1Chemaxon
Polarizability9.65 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9043
Blood Brain Barrier+0.6942
Caco-2 permeable-0.7184
P-glycoprotein substrateNon-substrate0.8441
P-glycoprotein inhibitor INon-inhibitor0.9826
P-glycoprotein inhibitor IINon-inhibitor0.9919
Renal organic cation transporterNon-inhibitor0.9591
CYP450 2C9 substrateNon-substrate0.8658
CYP450 2D6 substrateNon-substrate0.8834
CYP450 3A4 substrateNon-substrate0.8185
CYP450 1A2 substrateNon-inhibitor0.9427
CYP450 2C9 inhibitorNon-inhibitor0.9236
CYP450 2D6 inhibitorNon-inhibitor0.9509
CYP450 2C19 inhibitorNon-inhibitor0.9368
CYP450 3A4 inhibitorNon-inhibitor0.8544
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9882
Ames testNon AMES toxic0.9069
CarcinogenicityNon-carcinogens0.6088
BiodegradationReady biodegradable0.5893
Rat acute toxicity1.6609 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9876
hERG inhibition (predictor II)Non-inhibitor0.9854
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-MSsplash10-0a4i-9000000000-60f74eae2ee4808e697a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-431f193046ed22c6acea
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-b1356f62b156e2ff22e7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-9000000000-7e475341edd49da8bf51
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-9800000000-be16cfbb30a5c433eeca
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-7241cd4aec9d81e580b8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-0f0f2a0ce221a0921689
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-116.24919
predicted
DeepCCS 1.0 (2019)
[M+H]+119.473816
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.02083
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. L-amino-acid oxidase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
L-amino-acid oxidase activity
Specific Function
Lysosomal L-amino-acid oxidase with highest specific activity with phenylalanine. May play a role in lysosomal antigen processing and presentation (By similarity).
Gene Name
IL4I1
Uniprot ID
Q96RQ9
Uniprot Name
L-amino-acid oxidase
Molecular Weight
62880.52 Da
References
  1. 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]
Details2. 1-aminocyclopropane-1-carboxylate synthase-like protein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Does not catalyze the synthesis of 1-aminocyclopropane-1-carboxylate but is capable of catalyzing the deamination of L-vinylglycine.
Gene Name
ACCS
Uniprot ID
Q96QU6
Uniprot Name
1-aminocyclopropane-1-carboxylate synthase-like protein 1
Molecular Weight
57323.03 Da
References
  1. Satoh S, Yang SF: Inactivation of 1-Aminocyclopropane-1-Carboxylate Synthase by l-Vinylglycine as Related to the Mechanism-Based Inactivation of the Enzyme by S-Adenosyl-l-Methionine. Plant Physiol. 1989 Nov;91(3):1036-9. [Article]

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