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Record Information
StatusDetected and Quantified
Creation Date2006-08-12 20:15:26 UTC
Update Date2020-10-09 21:03:09 UTC
Secondary Accession Numbers
  • HMDB03406
Metabolite Identification
Common NameD-Serine
DescriptionD-serine is a stereo-isomer of the common amino acid, L-serine. D-serine was only thought to exist in bacteria until relatively recently. D-serine was the second D amino acid discovered to naturally exist in humans. The first one was D-aspartate. D-serine is synthesized from L-serine by serine racemase (SRR), and it is degraded by D-amino acid oxidase (DAO). It is found in high abundance in the brain. D-serine acts on the glycine binding site of the N-methyl-D-aspartate receptor (NMDAR) and modulates glutamate-mediated receptor activation. For the receptor to open, glutamate and either glycine or D-serine must bind to it. In fact, D-serine is a more potent agonist at the glycine site on the NMDAR than glycine itself. The importance of D-serine in mammalian brain function is apparent from extensive investigations reported and reviewed over the past decade, including roles in synaptic plasticity and memory. D-serine is also implicated in the pathophysiology and therapy of several psychiatric and neurological conditions including schizophrenia and glioma. In schizophrenia, there is evidence that D-serine levels are decreased, a deficiency that may contribute to the proposed NMDAR hypofunction of the disorder and that has led to D-serine replenishment as a novel therapeutic strategy.
(2R)-2-Amino-3-hydroxypropanoic acidChEBI
(R)-2-Amino-3-hydroxy-propionic acidChEBI
(R)-2-Amino-3-hydroxypropanoic acidChEBI
Serine D-formHMDB
Chemical FormulaC3H7NO3
Average Molecular Weight105.0926
Monoisotopic Molecular Weight105.042593095
IUPAC Name(2R)-2-amino-3-hydroxypropanoic acid
Traditional NameD-serine
CAS Registry Number312-84-5
InChI Identifier
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
  • 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
Physiological effect

Health effect:


Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting Point229 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility364 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility480 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06sl-9000000000-033631650075b940e0e2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-9810000000-06fed7f6e260b107d95aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-d33888cff00d0ade0ffeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9000000000-f7e50afcb90768dce4a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-043951ed5540cce44f4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08g0-9300000000-dab8446816db786db171Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-1a5aef91299ef3583ca2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b6cfe52e68c644cacfd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-6900000000-ee98a5a83ffbd434740eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-9200000000-fa8d04d6ce99a290d187Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-001b18464fb313594decSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Lung
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
Normal Concentrations
BloodDetected and Quantified1.88 +/- 0.07 uMAdult (>18 years old)Both
BloodDetected and Quantified2.28 +/- 0.59 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.6 +/- 2.2 uMAdult (>18 years old)MaleNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
UrineDetected and Quantified0.0021 - 10.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified1.57 +/- 0.07 uMAdult (>18 years old)Both
BloodDetected and Quantified1.86 +/- 0.53 uMAdult (>18 years old)BothSchizophrenia details
UrineDetected and Quantified0.0041 - 0.0122 umol/mmol creatinineAdult (>18 years old)BothADPKD details
Associated Disorders and Diseases
Disease References
  1. Hashimoto K, Fukushima T, Shimizu E, Komatsu N, Watanabe H, Shinoda N, Nakazato M, Kumakiri C, Okada S, Hasegawa H, Imai K, Iyo M: Decreased serum levels of D-serine in patients with schizophrenia: evidence in support of the N-methyl-D-aspartate receptor hypofunction hypothesis of schizophrenia. Arch Gen Psychiatry. 2003 Jun;60(6):572-6. [PubMed:12796220 ]
  2. Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Associated OMIM IDs
  • 181500 (Schizophrenia)
  • 601313 (Autosomal dominant polycystic kidney disease)
DrugBank IDDB03929
Phenol Explorer Compound IDNot Available
FooDB IDFDB023164
KNApSAcK IDNot Available
Chemspider ID64231
KEGG Compound IDC00740
BiGG ID35846
Wikipedia LinkSerine
PubChem Compound71077
PDB IDNot Available
ChEBI ID16523
Food Biomarker OntologyNot Available
MarkerDB IDMDB00000423
Synthesis ReferenceZhu, Yanxin; Yuan, Minglong; Yuan, Mingwei; Du, Bilin; Zheng, Ling. Preparation of D-serine from acetylglycine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 4pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  11. Hooper JD, Nicol DL, Dickinson JL, Eyre HJ, Scarman AL, Normyle JF, Stuttgen MA, Douglas ML, Loveland KA, Sutherland GR, Antalis TM: Testisin, a new human serine proteinase expressed by premeiotic testicular germ cells and lost in testicular germ cell tumors. Cancer Res. 1999 Jul 1;59(13):3199-205. [PubMed:10397266 ]
  12. Ishida-Takahashi R, Rosario F, Gong Y, Kopp K, Stancheva Z, Chen X, Feener EP, Myers MG Jr: Phosphorylation of Jak2 on Ser(523) inhibits Jak2-dependent leptin receptor signaling. Mol Cell Biol. 2006 Jun;26(11):4063-73. [PubMed:16705160 ]
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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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
L-Serine → D-Serinedetails
D-Serine → Pyruvic acid + Ammoniadetails