O-acetyl-L-serine

Identification

Name
O-acetyl-L-serine
Accession Number
DB01837  (EXPT02411)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • L-Serine, acetate (ester)
  • O3-acetyl-L-serine
External IDs
NSC-226230
Categories
Not Available
UNII
G05L7T7ZEQ
CAS number
5147-00-2
Weight
Average: 147.1293
Monoisotopic: 147.053157781
Chemical Formula
C5H9NO4
InChI Key
VZXPDPZARILFQX-BYPYZUCNSA-N
InChI
InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
IUPAC Name
(2S)-3-(acetyloxy)-2-aminopropanoic acid
SMILES
CC(=O)OC[C@H](N)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProstaglandin G/H synthase 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Walfred Leinfelder, Peter Heinrich, "Process for preparing O-acetylserine, L-cysteine and L-cysteine-related products." U.S. Patent US6218168, issued October, 1990.

US6218168
General References
Not Available
External Links
Human Metabolome Database
HMDB0003011
KEGG Compound
C00979
PubChem Compound
99478
PubChem Substance
46507422
ChemSpider
89874
ChEBI
17981
HET
OAS
Wikipedia
O-Acetylserine
PDB Entries
1ebv / 2c58 / 2vav / 2vax / 3fyu / 3n8y / 3vsd / 4cqm / 4lq2 / 4lq5
show 14 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility174.0 mg/mLALOGPS
logP-2.8ALOGPS
logP-3.4ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.62 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.19 m3·mol-1ChemAxon
Polarizability13.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8137
Blood Brain Barrier-0.5401
Caco-2 permeable-0.833
P-glycoprotein substrateNon-substrate0.5694
P-glycoprotein inhibitor INon-inhibitor0.9679
P-glycoprotein inhibitor IINon-inhibitor0.9795
Renal organic cation transporterNon-inhibitor0.9342
CYP450 2C9 substrateNon-substrate0.8498
CYP450 2D6 substrateNon-substrate0.8515
CYP450 3A4 substrateNon-substrate0.7801
CYP450 1A2 substrateNon-inhibitor0.8483
CYP450 2C9 inhibitorNon-inhibitor0.9369
CYP450 2D6 inhibitorNon-inhibitor0.9132
CYP450 2C19 inhibitorNon-inhibitor0.9515
CYP450 3A4 inhibitorNon-inhibitor0.8822
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9947
Ames testNon AMES toxic0.7432
CarcinogenicityNon-carcinogens0.8485
BiodegradationReady biodegradable0.8016
Rat acute toxicity1.5968 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.993
hERG inhibition (predictor II)Non-inhibitor0.9838
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-01c0-0900000000-cbac2ae436dcca0d0251
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-01c0-0900000000-7c5ef6cc55e1a01984af
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-6900000000-f2863fb0291664c5ca21
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00yi-0910000000-4eb5131c64279fbabbfb
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-01c0-0900000000-cbac2ae436dcca0d0251
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-01c0-0900000000-7c5ef6cc55e1a01984af
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-6900000000-f2863fb0291664c5ca21
GC-MS Spectrum - GC-MSGC-MSsplash10-00yi-0910000000-4eb5131c64279fbabbfb
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-052r-9700000000-798191f65808f670b0b8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052r-9700000000-798191f65808f670b0b8
1H NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound 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
Dicarboxylic acids and derivatives / Carboxylic acid esters / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
acetate ester, acetyl-L-serine (CHEBI:17981)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:07