Identification
- Generic Name
- D-Serine
- DrugBank Accession Number
- DB03929
- Background
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]
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for D-Serine (DB03929)
- Weight
- Average: 105.0926
Monoisotopic: 105.042593095 - Chemical Formula
- C3H7NO3
- Synonyms
- Not Available
- External IDs
- NSC-77689
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGlutamate receptor ionotropic, NMDA 1 Not Available Humans UGlycine receptor subunit alpha-1 Not Available Humans USerpin B3 Not Available Humans UHead decoration protein Not Available Bacteriophage 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- Alcohol / Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Beta-hydroxy acid / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- D-alpha-amino acid, serine (CHEBI:16523) / Other amino acids (C00740)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1K77H2Z9B1
- CAS number
- 312-84-5
- 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[C@H](CO)C(O)=O
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
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0003406
- KEGG Compound
- C00740
- PubChem Compound
- 71077
- PubChem Substance
- 46508200
- ChemSpider
- 64231
- BindingDB
- 23167
- 1742747
- ChEBI
- 16523
- ChEMBL
- CHEMBL285123
- ZINC
- ZINC000000895342
- Therapeutic Targets Database
- DCL000784
- PDBe Ligand
- DSN
- Wikipedia
- Serine
- PDB Entries
- 185d / 193d / 1bfw / 1cyn / 1pb8 / 1pfe / 1t5m / 1t5n / 1td4 / 1uhg … show 149 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Parkinson's Disease (PD) 1 4 Completed Treatment Gilles de la Tourette's Syndrome 1 3 Completed Treatment Schizoaffective Disorders / Schizophrenia 2 2 Completed Treatment Post Traumatic Stress Disorder (PTSD) 1 2 Completed Treatment Psychosis / Schizophrenia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 229 dec °C PhysProp water solubility 3.64E+005 mg/L (at 20 °C) BEILSTEIN - Predicted Properties
Property Value Source Water Solubility 480.0 mg/mL ALOGPS logP -3.4 ALOGPS logP -3.9 Chemaxon logS 0.66 ALOGPS pKa (Strongest Acidic) 2.03 Chemaxon pKa (Strongest Basic) 8.93 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 83.55 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 22.04 m3·mol-1 Chemaxon Polarizability 9.39 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9407 Blood Brain Barrier - 0.6529 Caco-2 permeable - 0.7839 P-glycoprotein substrate Non-substrate 0.7693 P-glycoprotein inhibitor I Non-inhibitor 0.9862 P-glycoprotein inhibitor II Non-inhibitor 0.9877 Renal organic cation transporter Non-inhibitor 0.9436 CYP450 2C9 substrate Non-substrate 0.8673 CYP450 2D6 substrate Non-substrate 0.846 CYP450 3A4 substrate Non-substrate 0.8389 CYP450 1A2 substrate Non-inhibitor 0.9087 CYP450 2C9 inhibitor Non-inhibitor 0.9512 CYP450 2D6 inhibitor Non-inhibitor 0.9349 CYP450 2C19 inhibitor Non-inhibitor 0.945 CYP450 3A4 inhibitor Non-inhibitor 0.908 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9914 Ames test Non AMES toxic 0.9088 Carcinogenicity Non-carcinogens 0.82 Biodegradation Ready biodegradable 0.9489 Rat acute toxicity 1.2700 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9923 hERG inhibition (predictor II) Non-inhibitor 0.9811
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 114.0066684 predictedDarkChem Lite v0.1.0 [M-H]- 113.9510684 predictedDarkChem Lite v0.1.0 [M-H]- 114.8380684 predictedDarkChem Lite v0.1.0 [M-H]- 115.068985 predictedDeepCCS 1.0 (2019) [M+H]+ 115.1920684 predictedDarkChem Lite v0.1.0 [M+H]+ 114.3997684 predictedDarkChem Lite v0.1.0 [M+H]+ 115.6429684 predictedDarkChem Lite v0.1.0 [M+H]+ 117.86859 predictedDeepCCS 1.0 (2019) [M+Na]+ 114.2710684 predictedDarkChem Lite v0.1.0 [M+Na]+ 113.8607684 predictedDarkChem Lite v0.1.0 [M+Na]+ 126.183334 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52