NAV

L-2-amino-3-butynoic acid

Identification

Generic Name
L-2-amino-3-butynoic acid
DrugBank Accession Number
DB04217
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 99.088
Monoisotopic: 99.032028409
Chemical Formula
C4H5NO2
Synonyms
  • (2S)-2-Amino-3-butynoic acid
External IDs
  • Antibiotic FR 900130
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCysteine desulfuraseNot AvailableEscherichia coli (strain K12)
UCystathionine gamma-lyaseNot 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 / Acetylides / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Acetylide / Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Fatty acid / Fatty acyl / Hydrocarbon derivative / L-alpha-amino acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
73537-09-4
InChI Key
DSUAJFIEKRKPEE-VKHMYHEASA-N
InChI
InChI=1S/C4H5NO2/c1-2-3(5)4(6)7/h1,3H,5H2,(H,6,7)/t3-/m0/s1
IUPAC Name
(2S)-2-aminobut-3-ynoic acid
SMILES
N[C@@H](C#C)C(O)=O

References

General References
Not Available
PubChem Compound
175496
PubChem Substance
46505992
ChemSpider
152908
PDBe Ligand
LPG
PDB Entries
1i29

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 Solubility1.5 mg/mLALOGPS
logP-2.2ALOGPS
logP-3Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.66Chemaxon
pKa (Strongest Basic)8.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area63.32 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity23.33 m3·mol-1Chemaxon
Polarizability9.09 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.805
Blood Brain Barrier+0.6267
Caco-2 permeable-0.807
P-glycoprotein substrateNon-substrate0.8747
P-glycoprotein inhibitor INon-inhibitor0.9913
P-glycoprotein inhibitor IINon-inhibitor0.9951
Renal organic cation transporterNon-inhibitor0.969
CYP450 2C9 substrateNon-substrate0.8544
CYP450 2D6 substrateNon-substrate0.8869
CYP450 3A4 substrateNon-substrate0.8315
CYP450 1A2 substrateNon-inhibitor0.9264
CYP450 2C9 inhibitorNon-inhibitor0.9216
CYP450 2D6 inhibitorNon-inhibitor0.9639
CYP450 2C19 inhibitorNon-inhibitor0.9556
CYP450 3A4 inhibitorNon-inhibitor0.9189
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.989
Ames testNon AMES toxic0.9105
CarcinogenicityNon-carcinogens0.632
BiodegradationReady biodegradable0.697
Rat acute toxicity1.3292 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9918
hERG inhibition (predictor II)Non-inhibitor0.9848
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-MSsplash10-0udi-9000000000-1434203d7278e1d69e15
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-9000000000-efce3faf31580b02a8d6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000000000-33cc26903e2aab5b586b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-9000000000-105882813d4a370f18a8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-9000000000-38e2e26b5f24e075d6de
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-9000000000-f60b7c70a7939f91031c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-9000000000-38be67376106f30ce1db
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]-115.4621088
predicted
DarkChem Lite v0.1.0
[M-H]-115.3296088
predicted
DarkChem Lite v0.1.0
[M-H]-112.65328
predicted
DeepCCS 1.0 (2019)
[M+H]+116.2468088
predicted
DarkChem Lite v0.1.0
[M+H]+116.2660088
predicted
DarkChem Lite v0.1.0
[M+H]+115.672386
predicted
DeepCCS 1.0 (2019)
[M+Na]+115.6449088
predicted
DarkChem Lite v0.1.0
[M+Na]+115.3481088
predicted
DarkChem Lite v0.1.0
[M+Na]+124.206795
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cysteine desulfurase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Selenocysteine lyase activity
Specific Function
Cysteine desulfurases mobilize the sulfur from L-cysteine to yield L-alanine, an essential step in sulfur metabolism for biosynthesis of a variety of sulfur-containing biomolecules. Component of th...
Gene Name
sufS
Uniprot ID
P77444
Uniprot Name
Cysteine desulfurase
Molecular Weight
44433.435 Da
References
  1. Mihara H, Fujii T, Kato S, Kurihara T, Hata Y, Esaki N: Structure of external aldimine of Escherichia coli CsdB, an IscS/NifS homolog: implications for its specificity toward selenocysteine. J Biochem. 2002 May;131(5):679-85. [Article]
Details2. Cystathionine gamma-lyase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two c...
Gene Name
CTH
Uniprot ID
P32929
Uniprot Name
Cystathionine gamma-lyase
Molecular Weight
44507.64 Da
References
  1. Yu S, Sugahara K, Nakayama K, Awata S, Kodama H: Accumulation of cystathionine, cystathionine ketimine, and perhydro-1,4-thiazepine-3,5-dicarboxylic acid in whole brain and various regions of the brain of D, L-propargylglycine-treated rats. Metabolism. 2000 Aug;49(8):1025-9. [Article]
  2. 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