Identification
- Generic Name
- Vinylglycine
- DrugBank Accession Number
- DB03214
- Background
Vinylglycine is an irreversible inhibitor of aspartate aminotransferase.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Vinylglycine (DB03214)
- Weight
- Average: 101.1039
Monoisotopic: 101.047678473 - Chemical Formula
- C4H7NO2
- Synonyms
- (2S)-2-amino-3-butenoic acid
- L-vinylglycine
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UL-amino-acid oxidase Not Available Humans U1-aminocyclopropane-1-carboxylate synthase-like protein 1 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.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
- 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
- External Links
- PDB Entries
- 1tdk
Clinical Trials
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 250.0 mg/mL ALOGPS logP -2.7 ALOGPS logP -2.5 ChemAxon logS 0.39 ALOGPS pKa (Strongest Acidic) 2.42 ChemAxon pKa (Strongest Basic) 8.95 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 63.32 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 24.91 m3·mol-1 ChemAxon Polarizability 9.65 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 + 0.9043 Blood Brain Barrier + 0.6942 Caco-2 permeable - 0.7184 P-glycoprotein substrate Non-substrate 0.8441 P-glycoprotein inhibitor I Non-inhibitor 0.9826 P-glycoprotein inhibitor II Non-inhibitor 0.9919 Renal organic cation transporter Non-inhibitor 0.9591 CYP450 2C9 substrate Non-substrate 0.8658 CYP450 2D6 substrate Non-substrate 0.8834 CYP450 3A4 substrate Non-substrate 0.8185 CYP450 1A2 substrate Non-inhibitor 0.9427 CYP450 2C9 inhibitor Non-inhibitor 0.9236 CYP450 2D6 inhibitor Non-inhibitor 0.9509 CYP450 2C19 inhibitor Non-inhibitor 0.9368 CYP450 3A4 inhibitor Non-inhibitor 0.8544 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9882 Ames test Non AMES toxic 0.9069 Carcinogenicity Non-carcinogens 0.6088 Biodegradation Ready biodegradable 0.5893 Rat acute toxicity 1.6609 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9876 hERG inhibition (predictor II) Non-inhibitor 0.9854
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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]
- 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
- 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