Identification

Name
D-Serine
Accession Number
DB03929  (EXPT01275)
Type
Small Molecule
Groups
Experimental, Investigational
Description

A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids. [PubChem]

Structure
Thumb
Synonyms
Not Available
External IDs
NSC-77689
Categories
Not Available
UNII
1K77H2Z9B1
CAS number
312-84-5
Weight
Average: 105.0926
Monoisotopic: 105.042593095
Chemical Formula
C3H7NO3
InChI Key
MTCFGRXMJLQNBG-UWTATZPHSA-N
InChI
InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1
IUPAC Name
(2R)-2-amino-3-hydroxypropanoic acid
SMILES
N[[email protected]](CO)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutamate receptor ionotropic, NMDA 1Not AvailableHuman
UGlycine receptor subunit alpha-1Not AvailableHuman
USerpin B3Not AvailableHuman
UHead decoration proteinNot AvailableBacteriophage 21
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
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
Hyperglycinemia, non-ketoticDisease
Tobramycin Action PathwayDrug action
Arbekacin Action PathwayDrug action
Methacycline Action PathwayDrug action
Clindamycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Netilmicin Action PathwayDrug action
Doxycycline Action PathwayDrug action
Minocycline Action PathwayDrug action
Lymecycline Action PathwayDrug action
Tigecycline Action PathwayDrug action
3-Phosphoglycerate dehydrogenase deficiencyDisease
Non Ketotic HyperglycinemiaDisease
Clarithromycin Action PathwayDrug action
Erythromycin Action PathwayDrug action
Roxithromycin Action PathwayDrug action
Kanamycin Action PathwayDrug action
Neomycin Action PathwayDrug action
Clomocycline Action PathwayDrug action
Dimethylglycine Dehydrogenase DeficiencyDisease
Paromomycin Action PathwayDrug action
Rolitetracycline Action PathwayDrug action
Chloramphenicol Action PathwayDrug action
Glycine and Serine MetabolismMetabolic
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)Disease
Dimethylglycine Dehydrogenase DeficiencyDisease
SarcosinemiaDisease
Azithromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Edward J. J. Grabowski, Paul J. Reider, "Preparation of 2-Deutero-D-serine." U.S. Patent US4582931, issued June, 1978.

US4582931
General References
  1. Hatanaka T, Huang W, Nakanishi T, Bridges CC, Smith SB, Prasad PD, Ganapathy ME, Ganapathy V: Transport of D-serine via the amino acid transporter ATB(0,+) expressed in the colon. Biochem Biophys Res Commun. 2002 Feb 22;291(2):291-5. [PubMed:11846403]
External Links
Human Metabolome Database
HMDB03406
KEGG Compound
C00740
PubChem Compound
71077
PubChem Substance
46508200
ChemSpider
64231
BindingDB
23167
ChEBI
16523
ChEMBL
CHEMBL285123
Therapeutic Targets Database
DCL000784
HET
DSN
PDB Entries
185d / 193d / 1bfw / 1cyn / 1pb8 / 1pfe / 1t5m / 1t5n / 1td4 / 1uhg
show 91 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentPosttraumatic Stress Disorders1
2CompletedTreatmentPsychosis / Psychotic Disorder NOS / Schizophrenias / Schizophrenic Disorders1
2CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2CompletedTreatmentSchizophrenia Prodrome1
2CompletedTreatmentSchizophrenic Disorders1
2Unknown StatusTreatmentSchizoaffective Disorders / Schizophrenic Disorders2
2Unknown StatusTreatmentSchizophrenic Disorders3
2WithdrawnTreatmentDependence, Cocaine1
3CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
3Unknown StatusTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
4CompletedNot AvailableParkinson's Disease (PD)1
4CompletedTreatmentGilles de la Tourette's Syndrome1

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)229 dec °CPhysProp
water solubility3.64E+005 mg/L (at 20 °C)BEILSTEIN
Predicted Properties
PropertyValueSource
Water Solubility480.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.04 m3·mol-1ChemAxon
Polarizability9.39 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9407
Blood Brain Barrier-0.6529
Caco-2 permeable-0.7839
P-glycoprotein substrateNon-substrate0.7693
P-glycoprotein inhibitor INon-inhibitor0.9862
P-glycoprotein inhibitor IINon-inhibitor0.9877
Renal organic cation transporterNon-inhibitor0.9436
CYP450 2C9 substrateNon-substrate0.8673
CYP450 2D6 substrateNon-substrate0.846
CYP450 3A4 substrateNon-substrate0.8389
CYP450 1A2 substrateNon-inhibitor0.9087
CYP450 2C9 inhibitorNon-inhibitor0.9512
CYP450 2D6 inhibitorNon-inhibitor0.9349
CYP450 2C19 inhibitorNon-inhibitor0.945
CYP450 3A4 inhibitorNon-inhibitor0.908
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9914
Ames testNon AMES toxic0.9088
CarcinogenicityNon-carcinogens0.82
BiodegradationReady biodegradable0.9489
Rat acute toxicity1.2700 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9923
hERG inhibition (predictor II)Non-inhibitor0.9811
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-03di-9000000000-d33888cff00d0ade0ffe
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-03di-9000000000-f7e50afcb90768dce4a5
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-043951ed5540cce44f4e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H 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 serine and derivatives. These 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Serine and derivatives
Alternative Parents
D-alpha-amino acids / Beta hydroxy acids and derivatives / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Primary alcohols / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 1 more
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
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-alpha-amino acid, serine (CHEBI:16523) / Other amino acids (C00740)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Voltage-gated cation channel activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Gene Name
GRIN1
Uniprot ID
Q05586
Uniprot Name
Glutamate receptor ionotropic, NMDA 1
Molecular Weight
105371.945 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transmitter-gated ion channel activity
Specific Function
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name
GLRA1
Uniprot ID
P23415
Uniprot Name
Glycine receptor subunit alpha-1
Molecular Weight
52623.35 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
May act as a papain-like cysteine protease inhibitor to modulate the host immune response against tumor cells. Also functions as an inhibitor of UV-induced apoptosis via suppression of the activity...
Gene Name
SERPINB3
Uniprot ID
P29508
Uniprot Name
Serpin B3
Molecular Weight
44564.315 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Bacteriophage 21
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Stabilizes the head shell following the rearrangement of the gp7 subunits of the head shell lattice that accompanies expansion of the head.
Gene Name
shp
Uniprot ID
P36275
Uniprot Name
Head decoration protein
Molecular Weight
11976.39 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Neurotransmitter:sodium symporter activity
Specific Function
Mediates the uptake of a broad range of neutral and cationic amino acids (with the exception of proline) in a Na(+)/Cl(-)-dependent manner.
Gene Name
SLC6A14
Uniprot ID
Q9UN76
Uniprot Name
Sodium- and chloride-dependent neutral and basic amino acid transporter B(0+)
Molecular Weight
72152.145 Da
References
  1. Hatanaka T, Huang W, Nakanishi T, Bridges CC, Smith SB, Prasad PD, Ganapathy ME, Ganapathy V: Transport of D-serine via the amino acid transporter ATB(0,+) expressed in the colon. Biochem Biophys Res Commun. 2002 Feb 22;291(2):291-5. [PubMed:11846403]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:34