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Record Information
Version1.0
Created at2020-03-18 23:25:56 UTC
Updated at2022-12-13 23:36:22 UTC
CannabisDB IDCDB000131
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Serine
Description
Structure
Thumb
Synonyms
Chemical FormulaC3H7NO3
Average Molecular Weight105.09
Monoisotopic Molecular Weight105.0426
IUPAC Name(2S)-2-amino-3-hydroxypropanoic acid
Traditional NameL-serine
CAS Registry Number6898-95-9
SMILES
N[C@@H](CO)C(O)=O
InChI Identifier
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1
InChI KeyMTCFGRXMJLQNBG-REOHCLBHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine 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 ParentSerine and derivatives
Alternative Parents
Substituents
  • Serine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • 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 Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility425 mg/mLNot Available
logP-3.07HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-3.4ALOGPS
logP-3.9ChemAxon
logS0.66ALOGPS
pKa (Strongest Acidic)2.03ChemAxon
pKa (Strongest Basic)8.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.04 m³·mol⁻¹ChemAxon
Polarizability9.39 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Serine--tRNA ligase, mitochondrialSARS219q13.2Q9NP81 details
Serine--tRNA ligase, cytoplasmicSARS1p13.3P49591 details
L-serine dehydratase/L-threonine deaminaseSDS12q24.13P20132 details
Cystathionine beta-synthaseCBS21q22.3P35520 details
Serine--pyruvate aminotransferaseAGXT2q37.3P21549 details
Serine hydroxymethyltransferase, mitochondrialSHMT212q12-q14P34897 details
Serine hydroxymethyltransferase, cytosolicSHMT117p11.2P34896 details
Serine palmitoyltransferase 1SPTLC19q22.2O15269 details
Phosphoserine phosphatasePSPH7p11.2P78330 details
Serine palmitoyltransferase 2SPTLC214q24.3O15270 details
Phosphatidylserine synthase 1PTDSS18q22P48651 details
Phosphatidylserine synthase 2PTDSS211p15.5Q9BVG9 details
Serine dehydratase-likeSDSL12q24.13Q96GA7 details
Serine palmitoyltransferase 3SPTLC320p12.1Q9NUV7 details
Serine racemaseSRR17p13Q9GZT4 details
Serine hydroxymethyltransferaseSHMT117p11.2A8MYA6 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Neutral amino acid transporter ASLC1A42p15-p13P43007 details
Monocarboxylate transporter 10SLC16A106q21-q22Q8TF71 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cystathionine beta-synthaseCBS21q22.3P35520 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.637 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified0.372 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified0.511 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified0.404 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.386 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified0.587 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0000187
DrugBank IDDB00133
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012739
KNApSAcK IDC00001393
Chemspider ID5736
KEGG Compound IDC00065
BioCyc IDSER
BiGG ID33717
Wikipedia LinkL-serine
METLIN ID5203
PubChem Compound5951
PDB IDNot Available
ChEBI ID17115
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 ]
  2. de Koning TJ, Snell K, Duran M, Berger R, Poll-The BT, Surtees R: L-serine in disease and development. Biochem J. 2003 May 1;371(Pt 3):653-61. doi: 10.1042/BJ20021785. [PubMed:12534373 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Catalyzes the attachment of serine to tRNA(Ser). Is also able to aminoacylate tRNA(Sec) with serine, to form the misacylated tRNA L-seryl-tRNA(Sec), which will be further converted into selenocysteinyl-tRNA(Sec) (By similarity).
Gene Name:
SARS2
Uniprot ID:
Q9NP81
Molecular weight:
58029.805
General function:
Involved in nucleotide binding
Specific function:
Catalyzes the attachment of serine to tRNA(Ser). Is also probably able to aminoacylate tRNA(Sec) with serine, to form the misacylated tRNA L-seryl-tRNA(Sec), which will be further converted into selenocysteinyl-tRNA(Sec).
Gene Name:
SARS
Uniprot ID:
P49591
Molecular weight:
58776.785
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
SDS
Uniprot ID:
P20132
Molecular weight:
34625.105
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
Only known pyridoxal phosphate-dependent enzyme that contains heme. Important regulator of hydrogen sulfide, especially in the brain, utilizing cysteine instead of serine to catalyze the formation of hydrogen sulfide. Hydrogen sulfide is a gastratransmitter with signaling and cytoprotective effects such as acting as a neuromodulator in the brain to protect neurons against hypoxic injury (By similarity).
Gene Name:
CBS
Uniprot ID:
P35520
Molecular weight:
60586.05
General function:
Involved in metabolic process
Specific function:
Not Available
Gene Name:
AGXT
Uniprot ID:
P21549
Molecular weight:
43009.535
General function:
Involved in catalytic activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Required to prevent uracil accumulation in mtDNA. Interconversion of serine and glycine. Associates with mitochondrial DNA.
Gene Name:
SHMT2
Uniprot ID:
P34897
Molecular weight:
54862.125
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine.
Gene Name:
SHMT1
Uniprot ID:
P34896
Molecular weight:
53082.18
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Serine palmitoyltransferase (SPT). The heterodimer formed with SPTLC2 or SPTLC3 constitutes the catalytic core. The composition of the serine palmitoyltransferase (SPT) complex determines the substrate preference. The SPTLC1-SPTLC2-SPTSSA complex shows a strong preference for C16-CoA substrate, while the SPTLC1-SPTLC3-SPTSSA isozyme uses both C14-CoA and C16-CoA as substrates, with a slight preference for C14-CoA. The SPTLC1-SPTLC2-SPTSSB complex shows a strong preference for C18-CoA substrate, while the SPTLC1-SPTLC3-SPTSSB isozyme displays an ability to use a broader range of acyl-CoAs, without apparent preference.
Gene Name:
SPTLC1
Uniprot ID:
O15269
Molecular weight:
52743.41
General function:
Involved in catalytic activity
Specific function:
Catalyzes the last step in the biosynthesis of serine from carbohydrates. The reaction mechanism proceeds via the formation of a phosphoryl-enzyme intermediates.
Gene Name:
PSPH
Uniprot ID:
P78330
Molecular weight:
25007.49
General function:
Involved in transferase activity
Specific function:
Serine palmitoyltransferase (SPT). The heterodimer formed with LCB1/SPTLC1 constitutes the catalytic core. The composition of the serine palmitoyltransferase (SPT) complex determines the substrate preference. The SPTLC1-SPTLC2-SPTSSA complex shows a strong preference for C16-CoA substrate, while the SPTLC1-SPTLC2-SPTSSB complex displays a preference for C18-CoA substrate.
Gene Name:
SPTLC2
Uniprot ID:
O15270
Molecular weight:
62923.765

Transporters

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:
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 19 proteins in total.