Identification

Name
Beta-Alanine
Accession Number
DB03107  (EXPT00624)
Type
Small Molecule
Groups
Experimental
Description

An amino acid formed in vivo by the degradation of dihydrouracil and carnosine. Since neuronal uptake and neuronal receptor sensitivity to beta-alanine have been demonstrated, the compound may be a false transmitter replacing GAMMA-AMINOBUTYRIC ACID. A rare genetic disorder, hyper-beta-alaninemia, has been reported. [PubChem]

Structure
Thumb
Synonyms
Not Available
External IDs
FEMA NO. 3252
Categories
UNII
11P2JDE17B
CAS number
107-95-9
Weight
Average: 89.0932
Monoisotopic: 89.047678473
Chemical Formula
C3H7NO2
InChI Key
UCMIRNVEIXFBKS-UHFFFAOYSA-N
InChI
InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
IUPAC Name
3-aminopropanoic acid
SMILES
NCCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPantothenate synthetaseNot AvailableMycobacterium tuberculosis
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
beta-Alanine MetabolismMetabolic
Histidine MetabolismMetabolic
Dihydropyrimidinase DeficiencyDisease
Aspartate MetabolismMetabolic
Propanoate MetabolismMetabolic
beta-Ureidopropionase DeficiencyDisease
Malonic AciduriaDisease
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Pantothenate and CoA BiosynthesisMetabolic
Pyrimidine MetabolismMetabolic
Aspartate MetabolismMetabolic
Methylmalonic Aciduria Due to Cobalamin-Related DisordersDisease
beta-Alanine MetabolismMetabolic
Propanoate MetabolismMetabolic
Canavan DiseaseDisease
HistidinemiaDisease
HypoacetylaspartiaDisease
UMP Synthase Deficiency (Orotic Aciduria)Disease
Malonyl-CoA Decarboxylase DeficiencyDisease
beta-Alanine MetabolismMetabolic
GABA-Transaminase DeficiencyDisease
Ureidopropionase DeficiencyDisease
Carnosinuria, CarnosinemiaDisease
Pantothenate and CoA Biosynthesis Metabolic
beta-Alanine MetabolismMetabolic
Histidine MetabolismMetabolic
Pyrimidine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Erwin Grill, Ernst-Ludwig Winnacker, Meinhart H. Zenk, "Cysteine-rich peptides having gamma-glutamic acid and beta-alanine units, a process for their preparation and their use." U.S. Patent US4883861, issued March, 1978.

US4883861
General References
Not Available
External Links
Human Metabolome Database
HMDB0000056
KEGG Compound
C00099
PubChem Compound
239
PubChem Substance
46507739
ChemSpider
234
BindingDB
50000102
ChEBI
57966
ChEMBL
CHEMBL297569
Therapeutic Targets Database
DNC000556
IUPHAR
2365
Guide to Pharmacology
GtP Drug Page
HET
BAL
Wikipedia
%CE%92-Alanine
PDB Entries
1efr / 1m19 / 1m1a / 1mcd / 1mce / 1mcf / 1mch / 1n2j / 1n2o / 1rgr
show 30 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)200 dec °CPhysProp
water solubility5.45E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.05TSAI,RS ET AL. (1991)
pKa3.63 (at 5 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility494.0 mg/mLALOGPS
logP-3.3ALOGPS
logP-3.2ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
pKa (Strongest Basic)10.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.7 m3·mol-1ChemAxon
Polarizability8.62 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9004
Blood Brain Barrier+0.7989
Caco-2 permeable-0.5996
P-glycoprotein substrateNon-substrate0.7836
P-glycoprotein inhibitor INon-inhibitor0.9654
P-glycoprotein inhibitor IINon-inhibitor0.9572
Renal organic cation transporterNon-inhibitor0.8567
CYP450 2C9 substrateNon-substrate0.8728
CYP450 2D6 substrateNon-substrate0.7638
CYP450 3A4 substrateNon-substrate0.7882
CYP450 1A2 substrateNon-inhibitor0.9235
CYP450 2C9 inhibitorNon-inhibitor0.9508
CYP450 2D6 inhibitorNon-inhibitor0.9696
CYP450 2C19 inhibitorNon-inhibitor0.9761
CYP450 3A4 inhibitorNon-inhibitor0.9583
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9847
Ames testNon AMES toxic0.8267
CarcinogenicityNon-carcinogens0.7603
BiodegradationReady biodegradable0.9607
Rat acute toxicity1.1302 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9149
hERG inhibition (predictor II)Non-inhibitor0.9221
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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-007k-1920000000-9389ee061bd6e9ae3b22
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0fdt-2930000000-5799fddb7fac04d22372
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-006t-1940000000-49f1b7c80f35cbcf102e
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-006t-2920000000-c701f2e5652fa4f35e50
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-8930000000-c4f8138d4cb7f1ea851a
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-014i-2900000000-c54f1d5878600393dca7
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0udi-1900000000-2f55a09bba074034dee7
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-00ds-2940000000-4192453eaba2cbecf800
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-006t-1960000000-665868f9adaa275dbdb3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-007k-1920000000-9389ee061bd6e9ae3b22
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fdt-2930000000-5799fddb7fac04d22372
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-006t-1940000000-49f1b7c80f35cbcf102e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-006t-2920000000-c701f2e5652fa4f35e50
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-8930000000-c4f8138d4cb7f1ea851a
GC-MS Spectrum - GC-MSGC-MSsplash10-00ds-2940000000-4192453eaba2cbecf800
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-2900000000-c54f1d5878600393dca7
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-1900000000-2f55a09bba074034dee7
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0900000000-efc0822e26bcf842e232
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0072-2920000000-284cff207c712b6698d6
Mass Spectrum (Electron Ionization)MSsplash10-001i-9000000000-be815b0a56f225da04d8
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00dl-9000000000-c30cc77c93e4ec09265a
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000j-9000000000-540a52fcec629c0a0647
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-000b-9000000000-531b17f8e16896225186
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-9000000000-61740a52186a51b8543c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-000i-9000000000-1bdf967935160468d550
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-000i-9000000000-0ba5264cfc5ec108718b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0006-9000000000-c6a2c78d322328400127
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-9000000000-d5f47100c42e7777802e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-001i-9000000000-e8f43be75c153e5be3cc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-1004-9000100000-ccb09493216d97165c8d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-00l7-9230000000-644b1dbe52c5f07e285a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0006-9000000000-ff4a990aa1fb1b7cc33d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-3ac278f3f0cfc3d50ebf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-9000000000-6d6e140cf4317b214296
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05dl-9000000000-ead5967d7f21631b6fc6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-91312dd333b1413fa045
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-007c-9000000000-caef7f2a75815a584747
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fdo-9000000000-5642be49ea98b530ff09
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-3ac278f3f0cfc3d50ebf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-9000000000-6d6e140cf4317b214296
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05dl-9000000000-ead5967d7f21631b6fc6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-9000000000-91312dd333b1413fa045
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-007c-9000000000-caef7f2a75815a584747
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fdo-9000000000-5642be49ea98b530ff09
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-61740a52186a51b8543c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-1bdf967935160468d550
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-0ba5264cfc5ec108718b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-c6a2c78d322328400127
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-9000000000-d5f47100c42e7777802e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-e8f43be75c153e5be3cc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-1004-9000100000-ccb09493216d97165c8d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00l7-9230000000-644b1dbe52c5f07e285a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-9000000000-ff4a990aa1fb1b7cc33d
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta 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
Beta amino acids and derivatives
Alternative Parents
Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Beta amino acid or derivatives / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Amine / Organic oxide / Hydrocarbon derivative / Primary amine / Organooxygen compound / Organonitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
beta-amino acid (CHEBI:16958) / Other amino acids, Biogenic amines (C00099)

Targets

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the condensation of pantoate with beta-alanine in an ATP-dependent reaction via a pantoyl-adenylate intermediate.
Specific Function
Atp binding
Gene Name
panC
Uniprot ID
P9WIL5
Uniprot Name
Pantothenate synthetase
Molecular Weight
32677.14 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. [PubMed:17139284]
  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. [PubMed:17016423]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:29