You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for Methionine sulfoxide (HMDB0002005)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:31 UTC
Update Date2021-09-14 15:46:58 UTC
HMDB IDHMDB0002005
Secondary Accession Numbers
  • HMDB02005
Metabolite Identification
Common NameMethionine sulfoxide
DescriptionMethionine sulfoxide 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. Methionine sulfoxide exists in all living species, ranging from bacteria to humans. Within humans, methionine sulfoxide participates in a number of enzymatic reactions. In particular, methionine sulfoxide can be biosynthesized from L-methionine through its interaction with the enzyme methionine-R-sulfoxide reductase B3. In addition, methionine sulfoxide can be biosynthesized from L-methionine through the action of the enzyme methionine-R-sulfoxide reductase b2, mitochondrial. In humans, methionine sulfoxide is involved in the metabolic disorder called hypermethioninemia.
Structure
Data?1582752222
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002005 (Methionine sulfoxide)


  Mrv1652305271900202D          

 10  9  0  0  0  0            999 V2000
10009.470810008.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10008.755210008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.040510008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.325410008.9496    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10006.606610008.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.325410009.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.184310008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.899910008.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.184310009.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.470810007.7121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
Download

3D MOL for HMDB0002005 (Methionine sulfoxide)

     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
    3.1694    0.3421    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2258   -0.9319    0.8605 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.3582   -2.2773    0.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5125   -0.3870    0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421   -0.1859   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844    0.2711   -0.3230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4810    1.5096    0.4273 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2828   -0.7807    0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3802   -1.9011   -0.2041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9274   -0.5243    1.5208 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496    1.2274   -0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6544   -0.0547   -0.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9765    0.6759    0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0651   -1.1248    1.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813    0.5742    1.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -1.1419   -1.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412    0.5850   -1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9124    0.5073   -1.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842    2.1296    0.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6137    2.0578    0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233   -0.5702    1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  6
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

3D SDF for HMDB0002005 (Methionine sulfoxide)


  Mrv1652305271900202D          

 10  9  0  0  0  0            999 V2000
10009.470810008.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10008.755210008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.040510008.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.325410008.9496    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10006.606610008.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.325410009.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.184310008.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.899910008.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.184310009.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.470810007.7121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002005

> <DATABASE_NAME>
hmdb

> <SMILES>
CS(=O)CC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
QEFRNWWLZKMPFJ-YGVKFDHGSA-N

> <FORMULA>
C5H11NO3S

> <MOLECULAR_WEIGHT>
165.21

> <EXACT_MASS>
165.045964392

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.984928749401364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-methanesulfinylbutanoic acid

> <ALOGPS_LOGP>
-2.40

> <JCHEM_LOGP>
-4.565261464903051

> <ALOGPS_LOGS>
-0.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7416965923493133

> <JCHEM_PKA_STRONGEST_BASIC>
9.11365628931558

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
39.3427

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-methionine sulfoxide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002005 (Methionine sulfoxide)

https://cactus.nci.nih.gov/chemical/structure/CS(=O)CC%5BC@H%5D(N)C(O)=O/file...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:20})
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.7991   -0.4386    0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    0.4948    0.0052 S   0  0  1  0  0  0  0  0  0  0  0  0
    2.5299    0.4149   -1.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -0.4080    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2895    0.2658    0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5293   -0.4957    0.4817 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5198   -0.5655    1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5243   -1.8464   -0.0958 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688    0.2366    0.0361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2023    1.3036    0.7256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3723   -0.1368   -0.9417 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7485    0.0214    0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6912   -0.4312    1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7764   -1.4672    0.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0144   -1.4372    0.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -0.4012    1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375    1.2951    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2525    0.2590   -1.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5328   -1.8086   -1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7362   -2.3800    0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0017    1.7405    0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  2  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 15  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  5 17  1  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  8 19  1  0  0  0  0
  8 20  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 21  1  0  0  0  0
M  END
$$$$
Download

PDB for HMDB0002005 (Methionine sulfoxide)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8684.3458682.603   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8683.0108683.373   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8681.6768682.603   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0    8680.3418683.373   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0    8678.9998682.600   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8680.3418684.912   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8685.6778683.373   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8687.0138682.603   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8685.6778684.912   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    8684.3458681.063   0.000  0.00  0.00           N+0
CONECT    1    2    7   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
Download

3D PDB for HMDB0002005 (Methionine sulfoxide)

COMPND    https://cactus.nci.nih.gov/chemical/structure/CS(=O)CC%5BC@H%5D(N)C(O)=O/file... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       3.799  -0.439   0.755  1.00  0.00           C  
HETATM    2  S   UNL     1       2.436   0.495   0.005  1.00  0.00           S  
HETATM    3  O   UNL     1       2.530   0.415  -1.410  1.00  0.00           O  
HETATM    4  C   UNL     1       0.966  -0.408   0.566  1.00  0.00           C  
HETATM    5  C   UNL     1      -0.289   0.266   0.009  1.00  0.00           C  
HETATM    6  CA  UNL     1      -1.529  -0.496   0.482  1.00  0.00           C  
HETATM    7  HA  UNL     1      -1.520  -0.566   1.569  1.00  0.00           H  
HETATM    8  N   UNL     1      -1.524  -1.846  -0.096  1.00  0.00           N  
HETATM    9  C   UNL     1      -2.769   0.237   0.036  1.00  0.00           C  
HETATM   10  O   UNL     1      -3.202   1.304   0.726  1.00  0.00           O  
HETATM   11  OXT UNL     1      -3.372  -0.137  -0.942  1.00  0.00           O  
HETATM   12  H   UNL     1       4.748   0.021   0.481  1.00  0.00           H  
HETATM   13  H   UNL     1       3.691  -0.431   1.840  1.00  0.00           H  
HETATM   14  H   UNL     1       3.776  -1.467   0.395  1.00  0.00           H  
HETATM   15  H   UNL     1       1.014  -1.437   0.210  1.00  0.00           H  
HETATM   16  H   UNL     1       0.929  -0.401   1.655  1.00  0.00           H  
HETATM   17  H   UNL     1      -0.338   1.295   0.364  1.00  0.00           H  
HETATM   18  H   UNL     1      -0.253   0.259  -1.081  1.00  0.00           H  
HETATM   19  H1  UNL     1      -1.533  -1.809  -1.104  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.736  -2.380   0.239  1.00  0.00           H  
HETATM   21  H   UNL     1      -4.002   1.740   0.401  1.00  0.00           H  
CONECT    1    2   12   13   14                                       
CONECT    2    1    3    3    4                                       
CONECT    3    2    2                                                 
CONECT    4    2    5   15   16                                       
CONECT    5    4    6   17   18                                       
CONECT    6    5    7    8    9                                       
CONECT    7    6                                                      
CONECT    8    6   19   20                                            
CONECT    9    6   10   11   11                                       
CONECT   10    9   21                                                 
CONECT   11    9    9                                                 
CONECT   12    1                                                      
CONECT   13    1                                                      
CONECT   14    1                                                      
CONECT   15    4                                                      
CONECT   16    4                                                      
CONECT   17    5                                                      
CONECT   18    5                                                      
CONECT   19    8                                                      
CONECT   20    8                                                      
CONECT   21   10                                                      
MASTER        0    0    0    0    0    0    0    0   21    0   21    0
END
Download

SMILES for HMDB0002005 (Methionine sulfoxide)

CS(=O)CC[C@H](N)C(O)=O
Download

INCHI for HMDB0002005 (Methionine sulfoxide)

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
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
L-Methionine sulfoxideChEBI
Methionine S-oxideChEBI
L-Methionine sulphoxideGenerator
Methionine sulphoxideGenerator
Methionine sulfoxide, (R-(r*,s*))-isomerHMDB
Methionine sulfoxide, 35S-labeled, (+-)-isomerHMDB
Methionine sulfoxide, (S-(r*,s*))-isomerHMDB
Methionine sulfoxide, (2S)-isomerHMDB
Methionine sulfoxide, (2R)-isomerHMDB
Methionine sulfoxide, (+-)-isomerHMDB
DL-Methionine sulfoxideHMDB
L-Methionine S-oxideHMDB
Methionine sulfoxideHMDB
Chemical FormulaC5H11NO3S
Average Molecular Weight165.21
Monoisotopic Molecular Weight165.045964392
IUPAC Name(2S)-2-amino-4-methanesulfinylbutanoic acid
Traditional NameL-methionine sulfoxide
CAS Registry Number3226-65-1
SMILES
CS(=O)CC[C@H](N)C(O)=O
InChI Identifier
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
InChI KeyQEFRNWWLZKMPFJ-YGVKFDHGSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Sulfoxide
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfinyl compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point232 - 234 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility54 g/LALOGPS
logP-2.4ALOGPS
logP-4.6ChemAxon
logS-0.49ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.34 m³·mol⁻¹ChemAxon
Polarizability15.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0900000000-6639ef576db5a01f8ee52019-05-22View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0910000000-4231d540eda02eebe8712019-05-22View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-004i-0900000000-f0849e8acf9a3e1e27632019-05-22View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-004i-1910000000-b7a64800b9e577e219d42019-05-22View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-1910000000-b7a64800b9e577e219d42019-05-22View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-a5138c4f03667c81645c2019-05-22View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0910000000-b8f17a35f754f6a2adff2019-05-22View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-004i-0900000000-40d23196cb4ee1cad23f2019-05-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0kmi-9300000000-40502e78936db0335f4a2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9400000000-cac8577601b69f1b723a2019-05-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-43361da834d0b07907fd2019-05-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-6090b56aa5a22d72fb4f2019-05-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9500000000-a4583e8c3a4365d330e22021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-433cb4a770ae8f69c6152021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ff3de228e84a6b4470bc2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9400000000-7375ade3d9a2e79890d42021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-9000000000-4fa3654466563449190c2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-375f7404d6c31bdf96b32021-09-07View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2019-05-22View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2019-05-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)2019-05-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2019-05-22View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.30-1.40 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.0 (3.0-5.0) uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified110 +/- 80 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified20 +/- 10 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified0.0444 +/- 0.0842 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.110 +/- 0.126 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified3.28 +/- 1.20 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified0.6418 +/- 0.4235 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
 details
UrineDetected and Quantified0.00-7.88 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
 details
UrineDetected and Quantified0.6-3.59 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
 details
UrineDetected and Quantified1.48 +/- 0.80 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
 details
UrineDetected and Quantified1.67 +/- 0.69 umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
 details
UrineDetected and Quantified< 0.132 umol/mmol creatinineAdult (>18 years old)BothNormal
      Not Available
 details
UrineDetected and Quantified0.31 (0.14-0.66) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified0.5038 +/- 0.5427 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
 details
UrineDetected and Quantified0.4259 +/- 0.5426 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022789
KNApSAcK IDNot Available
Chemspider ID139840
KEGG Compound IDC02989
BioCyc IDCPD0-1959
BiGG IDNot Available
Wikipedia LinkMethionine sulfoxide
METLIN ID6428
PubChem Compound158980
PDB IDNot Available
ChEBI ID17016
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schallreuter KU: Functioning methionine-S-sulfoxide reductases A and B are present in human skin. J Invest Dermatol. 2006 May;126(5):947-9. [PubMed:16619011 ]
  2. O'Donohue TL, Charlton CG, Thoa NB, Helke CJ, Moody TW, Pert A, Williams A, Miller RL, Jacobowitz DM: Release of alpha-melanocyte stimulating hormone into rat and human cerebrospinal fluid in vivo and from rat hypothalamus slices in vitro. Peptides. 1981 Spring;2(1):93-100. [PubMed:7243627 ]
  3. Boudier C, Cadene M, Bieth JG: Inhibition of neutrophil cathepsin G by oxidized mucus proteinase inhibitor. Effect of heparin. Biochemistry. 1999 Jun 29;38(26):8451-7. [PubMed:10387091 ]
  4. Mashima R, Nakanishi-Ueda T, Yamamoto Y: Simultaneous determination of methionine sulfoxide and methionine in blood plasma using gas chromatography-mass spectrometry. Anal Biochem. 2003 Feb 1;313(1):28-33. [PubMed:12576054 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details
1. Mitochondrial peptide methionine sulfoxide reductase
General function:
Involved in oxidoreductase activity, acting on a sulfur group of donors, disulfide as acceptor
Specific function:
Has an important function as a repair enzyme for proteins that have been inactivated by oxidation. Catalyzes the reversible oxidation-reduction of methionine sulfoxide in proteins to methionine.
Gene Name:
MSRA
Uniprot ID:
Q9UJ68
Molecular weight:
21737.41
Reactions
L-Methionine + thioredoxin disulfide + Water → Methionine sulfoxide + thioredoxindetails
Enzyme Details
2. Methionine-R-sulfoxide reductase B2, mitochondrial
General function:
Involved in peptide-methionine-(S)-S-oxide reductase activity
Specific function:
Catalyzes the reduction of free and protein-bound methionine sulfoxide to methionine (By similarity). Upon oxidative stress, may play a role in the preservation of mitochondrial integrity by decreasing the intracellular reactive oxygen species build-up through its scavenging role, hence contributing to cell survival and protein maintenance.
Gene Name:
MSRB2
Uniprot ID:
Q9Y3D2
Molecular weight:
19536.055
Enzyme Details
3. Methionine-R-sulfoxide reductase B3
General function:
Involved in peptide-methionine-(S)-S-oxide reductase activity
Specific function:
Catalyzes the reduction of free and protein-bound methionine sulfoxide to methionine. Isoform 2 is essential for hearing.
Gene Name:
MSRB3
Uniprot ID:
Q8IXL7
Molecular weight:
20010.23