NAV

L-methionine (S)-S-oxide

Identification

Generic Name
L-methionine (S)-S-oxide
DrugBank Accession Number
DB02467
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 165.211
Monoisotopic: 165.045963913
Chemical Formula
C5H11NO3S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThymidylate synthaseNot AvailableEscherichia coli (strain K12)
UPossible cellulase CelA1 (Endoglucanase) (Endo-1,4-beta-glucanase) (FI-cmcase) (Carboxymethyl cellulase)Not AvailableMycobacterium tuberculosis
URas-related protein Rab-5ANot AvailableHumans
UCellulase BNot AvailableStreptomyces lividans
UAmicyaninNot AvailableParacoccus denitrificans
UAminopeptidase SNot AvailableStreptomyces griseus
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
Thia fatty acids / Sulfoxides / Amino acids / Sulfinyl compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 1 more
Substituents
Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Fatty acid / Fatty acyl / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
L-methionine S-oxide (CHEBI:49031)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QEFRNWWLZKMPFJ-MFXDVPHUSA-N
InChI
InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10-/m0/s1
IUPAC Name
(2S)-2-azaniumyl-4-[(S)-methanesulfinyl]butanoate
SMILES
[H]C([H])([H])[S@](=O)C([H])([H])C([H])([H])[C@@]([H])(C([O-])=O)[N+]([H])([H])[H]

References

General References
Not Available
KEGG Compound
C15999
PubChem Compound
10909908
PubChem Substance
46508428
ChemSpider
9085165
ChEBI
49031
ZINC
ZINC000003861729
PDBe Ligand
MHO
PDB Entries
1ek0 / 1f4g / 1nlr / 1sf5 / 1st2 / 1up0 / 1up2 / 1xjo / 2a9e / 2idt …
show 32 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 Solubility54.0 mg/mLALOGPS
logP-2.4ALOGPS
logP-4.6Chemaxon
logS-0.49ALOGPS
pKa (Strongest Acidic)1.74Chemaxon
pKa (Strongest Basic)9.11Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area84.84 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity61.47 m3·mol-1Chemaxon
Polarizability16.12 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ldi-7900000000-b574e929048d3aaeef74
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-b160851aeeb2c4661165
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9100000000-8045451136efeb91f8ca
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-9000000000-41c6e97be0fd719493ad
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-9000000000-2ccd8dfaf2edb4163f4f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-17a52aa5cc12fa96f595
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]-134.7151722
predicted
DarkChem Lite v0.1.0
[M-H]-128.14986
predicted
DeepCCS 1.0 (2019)
[M+H]+135.8216722
predicted
DarkChem Lite v0.1.0
[M+H]+131.8957
predicted
DeepCCS 1.0 (2019)
[M+Na]+134.5781722
predicted
DarkChem Lite v0.1.0
[M+Na]+141.05553
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thymidylate synthase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis. This protein also binds to its mRNA thus repressing its own translation.
Gene Name
thyA
Uniprot ID
P0A884
Uniprot Name
Thymidylate synthase
Molecular Weight
30479.475 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]
Details2. Possible cellulase CelA1 (Endoglucanase) (Endo-1,4-beta-glucanase) (FI-cmcase) (Carboxymethyl cellulase)
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Cellulase activity
Specific Function
Not Available
Gene Name
celA1
Uniprot ID
Q79G13
Uniprot Name
Possible cellulase CelA1 (Endoglucanase) (Endo-1,4-beta-glucanase) (FI-cmcase) (Carboxymethyl cellulase)
Molecular Weight
39973.515 Da
Details3. Ras-related protein Rab-5A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Gtpase activity
Specific Function
The small GTPases Rab are key regulators of intracellular membrane trafficking, from the formation of transport vesicles to their fusion with membranes. Rabs cycle between an inactive GDP-bound for...
Gene Name
RAB5A
Uniprot ID
P20339
Uniprot Name
Ras-related protein Rab-5A
Molecular Weight
23658.5 Da
References
  1. 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]
Details4. Cellulase B
Kind
Protein
Organism
Streptomyces lividans
Pharmacological action
Unknown
General Function
Polysaccharide binding
Specific Function
Not Available
Gene Name
celB
Uniprot ID
Q54331
Uniprot Name
Cellulase B
Molecular Weight
39239.03 Da
Details5. Amicyanin
Kind
Protein
Organism
Paracoccus denitrificans
Pharmacological action
Unknown
General Function
Electron carrier activity
Specific Function
Primary acceptor of electrons from methylamine dehydrogenase. Passes those electrons on either a soluble cytochrome c or to pseudoazurin.
Gene Name
mauC
Uniprot ID
P22364
Uniprot Name
Amicyanin
Molecular Weight
13983.11 Da
Details6. Aminopeptidase S
Kind
Protein
Organism
Streptomyces griseus
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
An exopeptidase specific for larger hydrophobic amino acids (especially leucine), no cleavage occurs if the next residue is proline (PubMed:8444149).
Gene Name
Not Available
Uniprot ID
P80561
Uniprot Name
Aminopeptidase S
Molecular Weight
45939.31 Da

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:17