Identification
- Generic Name
- O-acetyl-L-serine
- DrugBank Accession Number
- DB01837
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for O-acetyl-L-serine (DB01837)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UProstaglandin G/H synthase 1 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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
- External Links
- 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 15 more
Clinical Trials
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
Property Value Source Water Solubility 174.0 mg/mL ALOGPS logP -2.8 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 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8137 Blood Brain Barrier - 0.5401 Caco-2 permeable - 0.833 P-glycoprotein substrate Non-substrate 0.5694 P-glycoprotein inhibitor I Non-inhibitor 0.9679 P-glycoprotein inhibitor II Non-inhibitor 0.9795 Renal organic cation transporter Non-inhibitor 0.9342 CYP450 2C9 substrate Non-substrate 0.8498 CYP450 2D6 substrate Non-substrate 0.8515 CYP450 3A4 substrate Non-substrate 0.7801 CYP450 1A2 substrate Non-inhibitor 0.8483 CYP450 2C9 inhibitor Non-inhibitor 0.9369 CYP450 2D6 inhibitor Non-inhibitor 0.9132 CYP450 2C19 inhibitor Non-inhibitor 0.9515 CYP450 3A4 inhibitor Non-inhibitor 0.8822 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9947 Ames test Non AMES toxic 0.7432 Carcinogenicity Non-carcinogens 0.8485 Biodegradation Ready biodegradable 0.8016 Rat acute toxicity 1.5968 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.993 hERG inhibition (predictor II) Non-inhibitor 0.9838
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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