Record Information
Version1.0
Created at2020-03-18 23:25:49 UTC
Updated at2020-12-07 19:07:08 UTC
CannabisDB IDCDB000128
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Alanine
DescriptionL-Alanine or Alanine, abbreviated Ala or A, is a non-essential amino acid made in the body from either the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. L-Alanine has been found to be associated with glucagon deficiency, which is an inborn error of metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. L-alanine is also found in Cannabis plants (PMID: 6991645 ).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Aminopropanoic acidChEBI
(S)-2-Aminopropanoic acidChEBI
(S)-AlanineChEBI
AChEBI
AlaChEBI
ALANINEChEBI
L-2-Aminopropionic acidChEBI
L-AlaninChEBI
L-alpha-AlanineChEBI
(2S)-2-AminopropanoateGenerator
(S)-2-AminopropanoateGenerator
L-2-AminopropionateGenerator
L-a-AlanineGenerator
L-Α-alanineGenerator
(S)-(+)-AlanineHMDB
(S)-2-Amino-propanoateHMDB
(S)-2-Amino-propanoic acidHMDB
2-AminopropanoateHMDB
2-Aminopropanoic acidHMDB
2-AminopropionateHMDB
2-Aminopropionic acidHMDB
2-AmmoniopropanoateHMDB
2-Ammoniopropanoic acidHMDB
a-AlanineHMDB
a-AminopropionateHMDB
a-Aminopropionic acidHMDB
alpha-AlanineHMDB
alpha-AminopropanoateHMDB
alpha-Aminopropanoic acidHMDB
alpha-AminopropionateHMDB
alpha-Aminopropionic acidHMDB
L-(+)-AlanineHMDB
L-2-AminopropanoateHMDB
L-2-Aminopropanoic acidHMDB
L-a-AminopropionateHMDB
L-a-Aminopropionic acidHMDB
L-alpha-AminopropionateHMDB
L-alpha-Aminopropionic acidHMDB
AbufèneHMDB
Alanine doms-adrian brandHMDB
Alanine, L-isomerHMDB
Doms-adrian brand OF alanineHMDB
Doms adrian brand OF alanineHMDB
L-Isomer alanineHMDB
Alanine, L isomerHMDB
L AlanineHMDB
Chemical FormulaC3H7NO2
Average Molecular Weight89.09
Monoisotopic Molecular Weight89.0477
IUPAC Name(2S)-2-aminopropanoic acid
Traditional NameL-alanine
CAS Registry Number115967-49-2
SMILES
C[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
InChI KeyQNAYBMKLOCPYGJ-REOHCLBHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlanine and derivatives
Alternative Parents
Substituents
  • Alanine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility204 mg/mLHuman Metabolome Project
logP-2.85SANGSTER (1994)
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-2.8ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.5 m³·mol⁻¹ChemAxon
Polarizability8.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Alanine, 1 TMS, GC-MS Spectrumsplash10-014i-0900000000-c7f6dbace291e8305a4eSpectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-381ddf4d9ea77be0b8a5Spectrum
GC-MSL-Alanine, 3 TMS, GC-MS Spectrumsplash10-01b9-6900000000-6a7c1bb2915e5dd0791fSpectrum
GC-MSL-Alanine, 2 TMS, GC-MS Spectrumsplash10-014i-1900000000-84b389f82562c29a8148Spectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-00kf-9000000000-b2f7507be509a85d821bSpectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-941672891ab94cf5015dSpectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-0f79-0910000000-47bd3e3aa274a653a64eSpectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-c7f6dbace291e8305a4eSpectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-381ddf4d9ea77be0b8a5Spectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-0a4i-1940000000-5def9f7c902aaf1ef607Spectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-01b9-6900000000-6a7c1bb2915e5dd0791fSpectrum
GC-MSL-Alanine, non-derivatized, GC-MS Spectrumsplash10-014i-1900000000-84b389f82562c29a8148Spectrum
Predicted GC-MSL-Alanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-d31f7a2ed8284a740b59Spectrum
Predicted GC-MSL-Alanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-ab365202f52df8e6d401Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-96b54b269c91ab21be08Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-a8008305399aa1097e1aSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-7253c912562200edc231Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-00kf-9000000000-72694f3a1a5de3b49790Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-55d0139f513946f76461Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-5b0dff13a98daf782205Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-37db595fcf7364600bc9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-5129e160acf979ac549eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-11c20eba8c5ad41d806cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-df7c7d6a6ae2d6bccefeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-32477244247613182214Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000f-9002000000-4873ce0cdcac54d68186Spectrum
MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0006-9000000000-8193842b36c819ca3ec6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-55d0139f513946f76461Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-5b0dff13a98daf782205Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-37db595fcf7364600bc9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-fefc31c264a2f0fcf6d0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-ba42bcd60aa9182a780eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-df7c7d6a6ae2d6bccefeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-080ffbbf05d95b7bcfe6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-0dfcc5cb0b7d9f01e04aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-130c999fe6b63419cfa1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2ddc0bb04bae8f928a23Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-98c403c9cd494594babfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-38a12affa4e4f4e91626Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
4-aminobutyrate aminotransferase, mitochondrialABAT16p13.2P80404 details
KynureninaseKYNU2q22.2Q16719 details
Alanine--glyoxylate aminotransferase 2, mitochondrialAGXT25p13Q9BYV1 details
Alanine--tRNA ligase, cytoplasmicAARS16q22P49588 details
Serine--pyruvate aminotransferaseAGXT2q37.3P21549 details
Alanine aminotransferase 1GPT8q24.3P24298 details
Peptidoglycan recognition protein 1PGLYRP1O75594 details
Cysteine desulfurase, mitochondrialNFS120q11.22Q9Y697 details
Alanine aminotransferase 2GPT216q12.1Q8TD30 details
Selenocysteine lyaseSCLY2q37.3Q96I15 details
5-phosphohydroxy-L-lysine phospho-lyaseAGXT2L25q35.3Q8IUZ5 details
Molybdenum cofactor sulfuraseMOCOS18q12Q96EN8 details
Peptidoglycan recognition protein 3PGLYRP3Q96LB9 details
Peptidoglycan recognition protein 4PGLYRP4Q96LB8 details
Alanine--tRNA ligase, mitochondrialAARS26p21.1Q5JTZ9 details
N-acetylmuramoyl-L-alanine amidasePGLYRP2Q96PD5 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Large neutral amino acids transporter small subunit 2SLC7A814q11.2Q9UHI5 details
Sodium-coupled neutral amino acid transporter 3SLC38A33p21.3Q99624 details
Neutral amino acid transporter ASLC1A42p15-p13P43007 details
Proton-coupled amino acid transporter 1SLC36A15q33.1Q7Z2H8 details
Monocarboxylate transporter 10SLC16A106q21-q22Q8TF71 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Alanine--tRNA ligase, cytoplasmicAARS16q22P49588 details
Molybdenum cofactor sulfuraseMOCOS18q12Q96EN8 details
Alanine--tRNA ligase, mitochondrialAARS26p21.1Q5JTZ9 details
N-acetylmuramoyl-L-alanine amidasePGLYRP2Q96PD5 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Peptidoglycan recognition protein 1PGLYRP1O75594 details
Peptidoglycan recognition protein 3PGLYRP3Q96LB9 details
Peptidoglycan recognition protein 4PGLYRP4Q96LB8 details
N-acetylmuramoyl-L-alanine amidasePGLYRP2Q96PD5 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified3.19 mg/g dry wt
    • Jiamin Zheng, Yil...
details
GabriolaDetected and Quantified3.78 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Island HoneyDetected and Quantified5.19 mg/g dry wt
    • Jiamin Zheng, Yil...
details
QuadraDetected and Quantified3.54 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Sensi StarDetected and Quantified5.07 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Tangerine DreamDetected and Quantified4.85 mg/g dry wt
    • Jiamin Zheng, Yil...
details
HMDB IDHMDB0000161
DrugBank IDDB00160
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000556
KNApSAcK IDC00001332
Chemspider ID5735
KEGG Compound IDC00041
BioCyc IDL-ALPHA-ALANINE
BiGG ID33629
Wikipedia LinkAlanine
METLIN IDNot Available
PubChem Compound5950
PDB IDNot Available
ChEBI ID16977
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Only showing the first 10 proteins. There are 29 proteins in total.

Enzymes

General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405
General function:
Involved in metabolic process
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
Q16719
Molecular weight:
34634.47
General function:
Involved in transaminase activity
Specific function:
Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:
AGXT2
Uniprot ID:
Q9BYV1
Molecular weight:
57155.905
General function:
Involved in nucleotide binding
Specific function:
Catalyzes the attachment of alanine to tRNA(Ala) in a two-step reaction: alanine is first activated by ATP to form Ala-AMP and then transferred to the acceptor end of tRNA(Ala). Also edits incorrectly charged tRNA(Ala) via its editing domain (By similarity).
Gene Name:
AARS
Uniprot ID:
P49588
Molecular weight:
106809.525
General function:
Involved in metabolic process
Specific function:
Not Available
Gene Name:
AGXT
Uniprot ID:
P21549
Molecular weight:
43009.535
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate. Participates in cellular nitrogen metabolism and also in liver gluconeogenesis starting with precursors transported from skeletal muscles (By similarity).
Gene Name:
GPT
Uniprot ID:
P24298
Molecular weight:
54636.415
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Pattern receptor that binds to murein peptidoglycans (PGN) of Gram-positive bacteria. Has bactericidal activity towards Gram-positive bacteria. May kill Gram-positive bacteria by interfering with peptidoglycan biosynthesis. Binds also to Gram-negative bacteria, and has bacteriostatic activity towards Gram-negative bacteria. Plays a role in innate immunity.
Gene Name:
PGLYRP1
Uniprot ID:
O75594
Molecular weight:
Not Available
General function:
Involved in metabolic process
Specific function:
Catalyzes the removal of elemental sulfur from cysteine to produce alanine. It supplies the inorganic sulfur for iron-sulfur (Fe-S) clusters. May be involved in the biosynthesis of molybdenum cofactor.
Gene Name:
NFS1
Uniprot ID:
Q9Y697
Molecular weight:
44361.485
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate.
Gene Name:
GPT2
Uniprot ID:
Q8TD30
Molecular weight:
46982.6
General function:
Involved in metabolic process
Specific function:
Catalyzes the decomposition of L-selenocysteine to L-alanine and elemental selenium (By similarity).
Gene Name:
SCLY
Uniprot ID:
Q96I15
Molecular weight:
48793.15

Transporters

General function:
Involved in transport
Specific function:
Sodium-independent, high-affinity transport of small and large neutral amino acids such as alanine, serine, threonine, cysteine, phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Acts as an amino acid exchanger. Has higher affinity for L-phenylalanine than LAT1 but lower affinity for glutamine and serine. L-alanine is transported at physiological concentrations. Plays a role in basolateral (re)absorption of neutral amino acids. Involved in the uptake of methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes, and hence plays a role in metal ion homeostasis and toxicity. Involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L-nitrosocysteine (L-CNSO) across the transmembrane. Plays an essential role in the reabsorption of neutral amino acids from the epithelial cells to the bloodstream in the kidney
Gene Name:
SLC7A8
Uniprot ID:
Q9UHI5
Molecular weight:
58381.1
General function:
Amino acid transport and metabolism
Specific function:
Sodium-dependent amino acid/proton antiporter. Mediates electrogenic cotransport of glutamine and sodium ions in exchange for protons. Also recognizes histidine, asparagine and alanine. May mediate amino acid transport in either direction under physiological conditions. May play a role in nitrogen metabolism and synaptic transmission
Gene Name:
SLC38A3
Uniprot ID:
Q99624
Molecular weight:
55772.4
General function:
Involved in sodium:dicarboxylate symporter activity
Specific function:
Transporter for alanine, serine, cysteine, and threonine. Exhibits sodium dependence
Gene Name:
SLC1A4
Uniprot ID:
P43007
Molecular weight:
55722.5
General function:
Amino acid transport and metabolism
Specific function:
Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid
Gene Name:
SLC36A1
Uniprot ID:
Q7Z2H8
Molecular weight:
53075.0
General function:
Involved in transmembrane transport
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
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular weight:
55492.1

Only showing the first 10 proteins. There are 29 proteins in total.