Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2018-01-23 19:25:01 UTC
Primary IDFDB012739
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Serine
DescriptionDietary supplement. L-Serine is found in many foods, some of which are cold cut, mammee apple, coho salmon, and carrot.
CAS Number56-45-1
Structure
Thumb
Synonyms
SynonymSource
2-amino-3-Hydroxypropionic acidChEBI
3-HydroxyalanineChEBI
SerinChEBI
2-amino-3-HydroxypropionateGenerator
2-amino-3-HydroxypropanoateGenerator
(-)-serinebiospider
(2S)-2-amino-3-HydroxypropanoateGenerator
(2S)-2-amino-3-hydroxypropanoic acidbiospider
(s)-(-)-serinebiospider
(S)-2-amino-3-hydroxy-Propanoatebiospider
(S)-2-amino-3-hydroxy-Propanoic acidbiospider
(S)-2-Amino-3-hydroxypropanoatebiospider
(S)-2-Amino-3-hydroxypropanoic acidbiospider
(S)-2-Amino-3-hydroxypropionic acidbiospider
(s)-a-amino-b-hydroxypropionatebiospider
(s)-a-amino-b-hydroxypropionic acidbiospider
(s)-alpha-amino-beta-hydroxypropionatebiospider
(s)-alpha-amino-beta-hydroxypropionic acidbiospider
(S)-b-Amino-3-hydroxypropionatebiospider
(S)-b-Amino-3-hydroxypropionic acidbiospider
(S)-beta-Amino-3-hydroxypropionatebiospider
(S)-beta-Amino-3-hydroxypropionic acidbiospider
(s)-serinebiospider
(S)-α-amino-β-hydroxypropionateGenerator
(S)-α-amino-β-hydroxypropionic acidGenerator
2-amino-3-Hydroxypropanoic acidHMDB
3-hydroxy-L-Alaninebiospider
Alpha-amino-beta-hydroxypropionic acidbiospider
B-hydroxy-l-alaninebiospider
b-HydroxyalanineGenerator
Beta-hydroxy-l-alaninebiospider
Beta-hydroxyalaninebiospider
L-(-)-serinebiospider
l-2-Amino-3-hydroxy-propanoic acidbiospider
L-2-amino-3-HydroxypropionateGenerator
l-2-Amino-3-hydroxypropionic acidbiospider
L-3-Hydroxy-2-aminopropionatebiospider
L-3-Hydroxy-2-aminopropionic acidbiospider
L-3-Hydroxy-alaninebiospider
L-serbiospider
L-SerinChEBI
L-Serinebiospider
SChEBI
SerChEBI
SERINEChEBI
Serine; L-formdb_source
β-hydroxy-L-alanineGenerator
β-hydroxyalanineGenerator
Predicted Properties
PropertyValueSource
Water Solubility480 g/LALOGPS
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
Polarizability9.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC3H7NO3
IUPAC name2-amino-3-hydroxypropanoic acid
InChI IdentifierInChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)
InChI KeyMTCFGRXMJLQNBG-UHFFFAOYSA-N
Isomeric SMILESNC(CO)C(O)=O
Average Molecular Weight105.0926
Monoisotopic Molecular Weight105.042593095
Classification
DescriptionThis 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.
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
  • 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 34.29%; H 6.71%; N 13.33%; O 45.67%DFC
Melting PointMp 228° dec.DFC
Boiling PointNot Available
Experimental Water Solubility425 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.07HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.34 (15°, 0.2M KNO3)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -69.5 (5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0159-1900000000-8e5f1894ee1cb3b7e3d9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-03di-0930000000-4dc3077a90bf3daff5c4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0960000000-72799edaa81cd10dc486View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0900000000-edb7de63d68f317dc1ddView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06sl-9000000000-23b7ff74f306e229e4edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-9810000000-06fed7f6e260b107d95aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-4900000000-3f93120669caa8042e73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-9100000000-0f9a39d1f5d7189dbec0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-9000000000-948720369b4759232b19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03dl-9000000000-ab6a722fc111a67e6756View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-20e689eb5cc63e11bd01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bti-9600000000-bc82bffef1dd9c4787b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dr-9000000000-f19f7b54ca6e6b6f90e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4r-9700000000-18d2c402d240f6209b00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01p9-9000000000-32aad5ff017e576a3cbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4r-9820000000-329e157e11708de1c960View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06ri-9320000000-7aeaceb154912fab6e7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ds-9030000000-07bab791f412b5ef2968View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ds-9120000000-81fcc8f743b2c1472458View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-3d77f3228dc2e322f724View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bti-9700000000-71eff48f7fa6167dfe43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01p9-9210000000-452ed7772dfc17d1f8b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bti-9500000000-03adc989c5c319caa262View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ds-9040000000-d0ca4931687f595af73dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-288773e12a924c5d1047View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06ri-9200000000-d1e0851b72d8c23ee443View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-4372abe1326c63681ba5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0d30b75120d259484b02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-8900000000-a5181e1e27d9d858893eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fe0-9200000000-dd033f8c8aa0e218a707View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-c4cee4145392d8715828View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0200-9000000000-dc5e2afcfab602641180View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID5736
ChEMBL IDCHEMBL11298
KEGG Compound IDC00065
Pubchem Compound ID5951
Pubchem Substance IDNot Available
ChEBI ID17115
Phenol-Explorer IDNot Available
DrugBank IDDB00133
HMDB IDHMDB00187
CRC / DFC (Dictionary of Food Compounds) IDBCP29-I:HKL05-W
EAFUS ID3390
Dr. Duke IDSERINE
BIGG ID33717
KNApSAcK IDC00001393
HET IDSER
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDL-Serine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
Enzymes
NameGene NameUniProt ID
Serine hydroxymethyltransferase, mitochondrialSHMT2P34897
Serine hydroxymethyltransferase, cytosolicSHMT1P34896
Serine palmitoyltransferase 1SPTLC1O15269
Phosphatidylserine synthase 1PTDSS1P48651
Phosphatidylserine synthase 2PTDSS2Q9BVG9
L-serine dehydratase/L-threonine deaminaseSDSP20132
Serine dehydratase-likeSDSLQ96GA7
Serine racemaseSRRQ9GZT4
Serine--tRNA ligase, mitochondrialSARS2Q9NP81
Serine--tRNA ligase, cytoplasmicSARSP49591
Serine palmitoyltransferase 2SPTLC2O15270
Serine palmitoyltransferase 3SPTLC3Q9NUV7
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Glycine and Serine MetabolismSMP00004 map00260
Homocysteine DegradationSMP00455 Not Available
Methionine MetabolismSMP00033 map00270
Sphingolipid MetabolismSMP00034 map00500
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).