O-acetyl-L-serine

Identification

Generic Name
O-acetyl-L-serine
DrugBank Accession Number
DB01837
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 147.1293
Monoisotopic: 147.053157781
Chemical Formula
C5H9NO4
Synonyms
  • L-Serine, acetate (ester)
  • O3-acetyl-L-serine
External IDs
  • NSC-226230

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProstaglandin G/H synthase 1Not AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Carboxylic acid ester / Dicarboxylic acid or derivatives / Hydrocarbon derivative / L-alpha-amino acid / Organic nitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
acetate ester, acetyl-L-serine (CHEBI:17981)
Affected organisms
Not Available

Chemical Identifiers

UNII
G05L7T7ZEQ
CAS number
5147-00-2
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

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
Human Metabolome Database
HMDB0003011
KEGG Compound
C00979
PubChem Compound
99478
PubChem Substance
46507422
ChemSpider
89874
ChEBI
17981
ChEMBL
CHEMBL1234916
ZINC
ZINC000000895446
PDBe Ligand
OAS
Wikipedia
O-Acetylserine
PDB Entries
1ebv / 2c58 / 2vav / 2vax / 3fyu / 3n8y / 3vsd / 4cqm / 4lq2 / 4lq5
show 16 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-0006-9000000000-1a24fb3faa274e72fcc5
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-052r-9700000000-798191f65808f670b0b8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9500000000-c190d16c705c1fd2b587
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-1ff5128772e970df3b63
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-992edd9a671914fdaa4a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-9100000000-a80a7a2a0fb27afd7f5f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-83186f964537081b52ba
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-eaf9d5d02a9bac29e251
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-130.5560365
predicted
DarkChem Lite v0.1.0
[M-H]-120.91009
predicted
DeepCCS 1.0 (2019)
[M+H]+131.1619365
predicted
DarkChem Lite v0.1.0
[M+H]+124.7315
predicted
DeepCCS 1.0 (2019)
[M+Na]+130.1915365
predicted
DarkChem Lite v0.1.0
[M+Na]+133.6791
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52