Record Information
Version1.0
Created at2020-04-17 18:54:27 UTC
Updated at2020-12-07 19:11:22 UTC
CannabisDB IDCDB004957
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameD-Serine
DescriptionD-Serine, also known as D-serin or DSN, 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. D-Serine is a very strong basic compound (based on its pKa). D-Serine exists in all living species, ranging from bacteria to humans. D-serine can be biosynthesized from L-serine through the action of the enzyme serine racemase. In humans, D-serine is involved in the metabolic disorder called non-ketotic hyperglycinemia. Outside of the human body, D-Serine has been detected, but not quantified in, several different foods, such as persian limes, mustard spinachs, black mulberries, epazotes, and wheats. This could make D-serine a potential biomarker for the consumption of these foods. The R-enantiomer of serine. D-Serine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
(2R)-2-Amino-3-hydroxypropanoic acidChEBI
(R)-2-Amino-3-hydroxy-propionic acidChEBI
(R)-2-Amino-3-hydroxypropanoic acidChEBI
D-SerinChEBI
DSNChEBI
(2R)-2-Amino-3-hydroxypropanoateGenerator
(R)-2-Amino-3-hydroxy-propionateGenerator
(R)-2-Amino-3-hydroxypropanoateGenerator
DL-SerineHMDB
Serine D-formHMDB
Chemical FormulaC3H7NO3
Average Molecular Weight105.09
Monoisotopic Molecular Weight105.0426
IUPAC Name(2R)-2-amino-3-hydroxypropanoic acid
Traditional NameD-serine
CAS Registry Number312-84-5
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-/m1/s1
InChI KeyMTCFGRXMJLQNBG-UWTATZPHSA-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
  • D-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 Point229 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility364 mg/mL at 20 °CNot Available
logPNot AvailableNot Available
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
TypeDescriptionSplash KeyView
Predicted GC-MSD-Serine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06sl-9000000000-033631650075b940e0e2Spectrum
Predicted GC-MSD-Serine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-9810000000-06fed7f6e260b107d95aSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-d33888cff00d0ade0ffeSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9000000000-f7e50afcb90768dce4a5Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-043951ed5540cce44f4eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08g0-9300000000-dab8446816db786db171Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-1a5aef91299ef3583ca2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b6cfe52e68c644cacfd7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-6900000000-ee98a5a83ffbd434740eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-9200000000-fa8d04d6ce99a290d187Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-001b18464fb313594decSpectrum
NMR
TypeDescriptionView
1D NMR1H 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
Phosphoserine phosphatasePSPH7p11.2P78330 details
Serine racemaseSRR17p13Q9GZT4 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Asc-type amino acid transporter 1SLC7A1019q13.1Q9NS82 details
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.55 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Sensi StarDetected and Quantified0.39 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Tangerine DreamDetected and Quantified0.62 mg/g dry wt
    • Jiamin Zheng, Yil...
details
HMDB IDHMDB0003406
DrugBank IDDB03929
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023164
KNApSAcK IDNot Available
Chemspider ID64231
KEGG Compound IDC00740
BioCyc IDD-SERINE
BiGG ID35846
Wikipedia LinkSerine
METLIN ID6920
PubChem Compound71077
PDB IDNot Available
ChEBI ID16523
References
General ReferencesNot Available

Enzymes

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 catalytic activity
Specific function:
Catalyzes the synthesis of D-serine from L-serine. D-serine is a key coagonist with glutamate at NMDA receptors. Has dehydratase activity towards both L-serine and D-serine.
Gene Name:
SRR
Uniprot ID:
Q9GZT4
Molecular weight:
36565.905

Transporters

General function:
Amino acid transport and metabolism
Specific function:
Sodium-independent, high affinity transport of small neutral D- and L-amino acids. May play a role in the modulation of glutamatergic transmission through mobilization of D-serine at the glutamatergic synapse
Gene Name:
SLC7A10
Uniprot ID:
Q9NS82
Molecular weight:
56797.4