You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameD-Serine
Accession NumberDB03929  (EXPT01275)
TypeSmall Molecule
GroupsExperimental
DescriptionA 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
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII1K77H2Z9B1
CAS number312-84-5
WeightAverage: 105.0926
Monoisotopic: 105.042593095
Chemical FormulaC3H7NO3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Tobramycin Action PathwayDrug actionSMP00711
Arbekacin Action PathwayDrug actionSMP00713
Methacycline Action PathwayDrug actionSMP00727
Amikacin Action PathwayDrug actionSMP00253
Spectinomycin Action PathwayDrug actionSMP00258
Hyperglycinemia, non-ketoticDiseaseSMP00485
Clindamycin Action PathwayDrug actionSMP00249
Gentamicin Action PathwayDrug actionSMP00254
Netilmicin Action PathwayDrug actionSMP00257
Doxycycline Action PathwayDrug actionSMP00291
Minocycline Action PathwayDrug actionSMP00292
Lymecycline Action PathwayDrug actionSMP00295
Tigecycline Action PathwayDrug actionSMP00712
3-Phosphoglycerate dehydrogenase deficiencyDiseaseSMP00721
Non Ketotic HyperglycinemiaDiseaseSMP00223
Clarithromycin Action PathwayDrug actionSMP00248
Erythromycin Action PathwayDrug actionSMP00250
Roxithromycin Action PathwayDrug actionSMP00251
Kanamycin Action PathwayDrug actionSMP00255
Neomycin Action PathwayDrug actionSMP00256
Clomocycline Action PathwayDrug actionSMP00262
Dimethylglycine Dehydrogenase DeficiencyDiseaseSMP00484
Paromomycin Action PathwayDrug actionSMP00714
Rolitetracycline Action PathwayDrug actionSMP00726
Chloramphenicol Action PathwayDrug actionSMP00729
Glycine and Serine MetabolismMetabolicSMP00004
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)DiseaseSMP00179
Dimethylglycine Dehydrogenase DeficiencyDiseaseSMP00242
SarcosinemiaDiseaseSMP00244
Azithromycin Action PathwayDrug actionSMP00247
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point229 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-d33888cff00d0ade0ffeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9000000000-f7e50afcb90768dce4a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-043951ed5540cce44f4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 plasticity, synaptogenesis, excitotoxicity, memory acquisition and learning. It mediates neuronal functions in glutamate neurotransmission. Is involved in the cell surface targeting of NMDA receptors (...
Gene Name:
GRIN1
Uniprot ID:
Q05586
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
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 of c-Jun NH(2)-terminal kinase (JNK1).
Gene Name:
SERPINB3
Uniprot ID:
P29508
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
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
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
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23