Back to Compounds

Showing Compound L-Serine (FDB012739)

Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2019-11-26 03:07:30 UTC
Primary IDFDB012739
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Serine
DescriptionL-Serine, also known as 3-hydroxyalanine or serin, 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. Thus, L-serine is considered to be a fatty acid lipid molecule. L-Serine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. L-Serine is found, on average, in the highest concentration within a few different foods, such as caseins, red bell peppers, and milk (cow) and in a lower concentration in yellow wax beans, butternut squash, and swiss chards. L-Serine has also been detected, but not quantified in, several different foods, such as cascade huckleberries, rocket salad (ssp.), alaska wild rhubarbs, climbing beans, and liquorices. This could make L-serine a potential biomarker for the consumption of these foods.
CAS Number56-45-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Amino-3-hydroxypropanoic acidChEBI
2-Amino-3-hydroxypropionic acidChEBI
3-HydroxyalanineChEBI
SerinChEBI
2-Amino-3-hydroxypropanoateGenerator
2-Amino-3-hydroxypropionateGenerator
(-)-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-HydroxypropanoateHMDB
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0200-9000000000-dc5e2afcfab6026411802014-09-20View Spectrum
GC-MSL-Serine, 2 TMS, GC-MS Spectrumsplash10-0159-1900000000-8e5f1894ee1cb3b7e3d9Spectrum
GC-MSL-Serine, 4 TMS, GC-MS Spectrumsplash10-03di-0930000000-4dc3077a90bf3daff5c4Spectrum
GC-MSL-Serine, non-derivatized, GC-MS Spectrumsplash10-0uxr-0960000000-72799edaa81cd10dc486Spectrum
GC-MSL-Serine, non-derivatized, GC-MS Spectrumsplash10-0159-0900000000-edb7de63d68f317dc1ddSpectrum
Predicted GC-MSL-Serine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06sl-9000000000-23b7ff74f306e229e4edSpectrum
Predicted GC-MSL-Serine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0089-9810000000-06fed7f6e260b107d95aSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-4900000000-3f93120669caa8042e732017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-9100000000-0f9a39d1f5d7189dbec02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-9000000000-948720369b4759232b192017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03dl-9000000000-ab6a722fc111a67e67562017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-20e689eb5cc63e11bd012017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bti-9600000000-bc82bffef1dd9c4787b62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dr-9000000000-f19f7b54ca6e6b6f90e12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4r-9700000000-18d2c402d240f6209b002017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01p9-9000000000-32aad5ff017e576a3cbe2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4r-9820000000-329e157e11708de1c9602017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06ri-9320000000-7aeaceb154912fab6e7c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ds-9030000000-07bab791f412b5ef29682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ds-9120000000-81fcc8f743b2c14724582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-3d77f3228dc2e322f7242017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bti-9700000000-71eff48f7fa6167dfe432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01p9-9210000000-452ed7772dfc17d1f8b42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0bti-9500000000-03adc989c5c319caa2622017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03ds-9040000000-d0ca4931687f595af73d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-288773e12a924c5d10472017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06ri-9200000000-d1e0851b72d8c23ee4432015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-4372abe1326c63681ba52015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-0d30b75120d259484b022015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-8900000000-a5181e1e27d9d858893e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fe0-9200000000-dd033f8c8aa0e218a7072015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-c4cee4145392d87158282015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 22.5 MHz, D2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.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).