AFCDB: L-Serine (FDB012739)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:20 UTC

Update date

2019-11-26 03:07:30 UTC

Primary ID

FDB012739

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Serine

Description

L-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 Number

56-45-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	480 g/L	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	9.45 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C3H7NO3

IUPAC name

2-amino-3-hydroxypropanoic acid

InChI Identifier

InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)

InChI Key

MTCFGRXMJLQNBG-UHFFFAOYSA-N

Isomeric SMILES

NC(CO)C(O)=O

Average Molecular Weight

105.0926

Monoisotopic Molecular Weight

105.042593095

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.

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino acid (CHEBI:17822 )
Amino fatty acids (LMFA01100045 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 34.29%; H 6.71%; N 13.33%; O 45.67%	DFC
Melting Point	Mp 228° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	425 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-3.07	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 9.34 (15°, 0.2M KNO3)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -69.5 (5M HCl)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0200-9000000000-dc5e2afcfab602641180	2014-09-20	View Spectrum
GC-MS	L-Serine, 2 TMS, GC-MS Spectrum	splash10-0159-1900000000-8e5f1894ee1cb3b7e3d9	Spectrum
GC-MS	L-Serine, 4 TMS, GC-MS Spectrum	splash10-03di-0930000000-4dc3077a90bf3daff5c4	Spectrum
GC-MS	L-Serine, non-derivatized, GC-MS Spectrum	splash10-0uxr-0960000000-72799edaa81cd10dc486	Spectrum
GC-MS	L-Serine, non-derivatized, GC-MS Spectrum	splash10-0159-0900000000-edb7de63d68f317dc1dd	Spectrum
Predicted GC-MS	L-Serine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-06sl-9000000000-23b7ff74f306e229e4ed	Spectrum
Predicted GC-MS	L-Serine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0089-9810000000-06fed7f6e260b107d95a	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-4900000000-3f93120669caa8042e73	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-9100000000-0f9a39d1f5d7189dbec0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-9000000000-948720369b4759232b19	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03dl-9000000000-ab6a722fc111a67e6756	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0900000000-20e689eb5cc63e11bd01	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0bti-9600000000-bc82bffef1dd9c4787b6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03dr-9000000000-f19f7b54ca6e6b6f90e1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4r-9700000000-18d2c402d240f6209b00	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01p9-9000000000-32aad5ff017e576a3cbe	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4r-9820000000-329e157e11708de1c960	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-06ri-9320000000-7aeaceb154912fab6e7c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03ds-9030000000-07bab791f412b5ef2968	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03ds-9120000000-81fcc8f743b2c1472458	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0900000000-3d77f3228dc2e322f724	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0bti-9700000000-71eff48f7fa6167dfe43	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01p9-9210000000-452ed7772dfc17d1f8b4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0bti-9500000000-03adc989c5c319caa262	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03ds-9040000000-d0ca4931687f595af73d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-0900000000-288773e12a924c5d1047	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06ri-9200000000-d1e0851b72d8c23ee443	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9000000000-4372abe1326c63681ba5	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-0d30b75120d259484b02	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-8900000000-a5181e1e27d9d858893e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fe0-9200000000-dd033f8c8aa0e218a707	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9000000000-c4cee4145392d8715828	2015-05-27	View Spectrum

NMR

Type	Description		View
1D NMR	¹³C NMR Spectrum (1D, 22.5 MHz, D₂O, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17115

Phenol-Explorer ID

Not Available

DrugBank ID

DB00133

HMDB ID

HMDB00187

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

L-Serine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Serine hydroxymethyltransferase, mitochondrial	SHMT2	P34897
Serine hydroxymethyltransferase, cytosolic	SHMT1	P34896
Serine palmitoyltransferase 1	SPTLC1	O15269
Phosphatidylserine synthase 1	PTDSS1	P48651
Phosphatidylserine synthase 2	PTDSS2	Q9BVG9
L-serine dehydratase/L-threonine deaminase	SDS	P20132
Serine dehydratase-like	SDSL	Q96GA7
Serine racemase	SRR	Q9GZT4
Serine--tRNA ligase, mitochondrial	SARS2	Q9NP81
Serine--tRNA ligase, cytoplasmic	SARS	P49591
Serine palmitoyltransferase 2	SPTLC2	O15270
Serine palmitoyltransferase 3	SPTLC3	Q9NUV7

Pathways

Name	SMPDB Link	KEGG Link
Ammonia Recycling	SMP00009	map00910
Glycine and Serine Metabolism	SMP00004	map00260
Homocysteine Degradation	SMP00455	Not Available
Methionine Metabolism	SMP00033	map00270
Sphingolipid Metabolism	SMP00034	map00500

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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).

L-Serine (FDB012739)

Structure for FDB012739 (L-Serine)