Showing Compound O-acetyl-L-serine (FDB031064)

Record Information

Version

1.0

Creation date

2015-05-07 20:55:50 UTC

Update date

2019-11-26 03:22:07 UTC

Primary ID

FDB031064

Secondary Accession Numbers

FDB004955
FDB023094

Chemical Information

FooDB Name

O-acetyl-L-serine

Description

O-acetyl-l-serine, also known as L-serine, acetate (ester) or (2s)-3-acetyloxy-2-aminopropanoate, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. O-acetyl-l-serine is soluble (in water) and a moderately acidic compound (based on its pKa). O-acetyl-l-serine can be found in a number of food items such as sorrel, summer savory, purslane, and cherimoya, which makes O-acetyl-l-serine a potential biomarker for the consumption of these food products. O-acetyl-l-serine can be found primarily in blood and urine, as well as in human prostate tissue. O-acetyl-l-serine exists in all living species, ranging from bacteria to humans.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
L-Serine, acetate (ester)	ChEBI
O3-Acetyl-L-serine	ChEBI
L-Serine, acetic acid (ester)	Generator
O-Acetyl-L-serine	HMDB
O-Acetyl-serine	HMDB
O-Acetylserine hydrobromide, (D)-isomer	HMDB
O-Acetylserine, (L)-isomer	HMDB
Serine acetate ester	HMDB
O-Acetylserine	MeSH

Predicted Properties

Property	Value	Source
Water Solubility	174 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-3.4	ChemAxon
logS	0.07	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	8.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.19 m³·mol⁻¹	ChemAxon
Polarizability	13.44 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

C5H9NO4

IUPAC name

(2S)-3-(acetyloxy)-2-aminopropanoic acid

InChI Identifier

InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1

InChI Key

VZXPDPZARILFQX-BYPYZUCNSA-N

Isomeric SMILES

CC(=O)OC[C@H](N)C(O)=O

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

Classification

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Amino acid
Carboxylic acid
Hydrocarbon derivative
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acetate ester (CHEBI:17981 )
acetyl-L-serine (CHEBI:17981 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Prostate

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	O-Acetyl-serine, 2 TMS, GC-MS Spectrum	splash10-01c0-0900000000-cbac2ae436dcca0d0251	Spectrum
GC-MS	O-Acetyl-serine, 2 TMS, GC-MS Spectrum	splash10-01c0-0900000000-7c5ef6cc55e1a01984af	Spectrum
GC-MS	O-Acetyl-serine, 2 TMS, GC-MS Spectrum	splash10-00di-6900000000-f2863fb0291664c5ca21	Spectrum
GC-MS	O-Acetyl-serine, 2 TMS, GC-MS Spectrum	splash10-00yi-0910000000-4eb5131c64279fbabbfb	Spectrum
GC-MS	O-Acetyl-serine, non-derivatized, GC-MS Spectrum	splash10-01c0-0900000000-cbac2ae436dcca0d0251	Spectrum
GC-MS	O-Acetyl-serine, non-derivatized, GC-MS Spectrum	splash10-01c0-0900000000-7c5ef6cc55e1a01984af	Spectrum
GC-MS	O-Acetyl-serine, non-derivatized, GC-MS Spectrum	splash10-00di-6900000000-f2863fb0291664c5ca21	Spectrum
GC-MS	O-Acetyl-serine, non-derivatized, GC-MS Spectrum	splash10-00yi-0910000000-4eb5131c64279fbabbfb	Spectrum
Predicted GC-MS	O-Acetyl-serine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-1a24fb3faa274e72fcc5	Spectrum
Predicted GC-MS	O-Acetyl-serine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-9300000000-048d27b5feab5a974f8d	Spectrum
Predicted GC-MS	O-Acetyl-serine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-052r-9700000000-798191f65808f670b0b8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-052r-9700000000-798191f65808f670b0b8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-0ai0-9000000000-48b5a588a0a890044838	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9400000000-6ea6ba6b54ea90c56416	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-05gj-9400000000-32253d09352cdfb8c318	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-022l-9000000000-155f852f94fd442482f2	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-e88b0e868a77f604b59c	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0089-9100000000-c7a43c74f2dde018ff1b	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00dj-9600000000-304c64ed85255dae12e8	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0btl-9400000000-7aa1b76f2e2dc6086311	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-fd8ce6d36426fce8d343	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-01bc-9000000000-abc90d9cacd4b889cd96	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-2900000000-d04884f0db647a14fc8d	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-052r-8900000000-c8515198104000e95777	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-4900000000-1942c426e3cf9c8b41c6	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-9400000000-8d3a49712627498e2c9b	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-052r-9700000000-cf8d37dfdbdee7d76628	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-052r-9700000000-32279928e0b151d0e1da	Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-6900000000-cb1c33a71a73963cf0c1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uea-3900000000-ef46289d46aa69d40d48	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-9700000000-221b830dc83fdf079527	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-52a79cff992a3a467f06	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-6900000000-4e0de865dfcc2446fe14	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9300000000-5a3f4b66b56fbaca505c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-123b2507eee8f6a9f064	Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound O-acetyl-L-serine (FDB031064)

Structure for FDB031064 (O-acetyl-L-serine)