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Showing NP-Card for Methionine sulfoxide (NP0000509)

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Record Information
Version2.0
Created at2006-05-22 14:17:31 UTC
Updated at2021-06-29 00:47:18 UTC
NP-MRD IDNP0000509
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000509 (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 NP0000509 (Methionine sulfoxide)

HMDB0002005
     RDKit          3D
Methionine sulfoxide
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.3419   -0.3882    0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6547   -0.6708    0.2572 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.4267   -1.9791   -0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224    0.7273   -0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.4930   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3102    0.2136    0.2766 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7349   -0.9661    0.8927 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293    0.0009    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2824   -1.0837    0.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160    0.9766   -0.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    0.6935    0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0641   -0.8159    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266   -0.8473    1.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032    1.0327   -1.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9762    1.5937    0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232    1.3797   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6219   -0.3701   -1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618    1.0814    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -1.7915    0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -1.0219    1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808    1.7419   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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  1
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

3D SDF for NP0000509 (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>
NP0000509

> <DATABASE_NAME>
NP-MRD

> <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 NP0000509 (Methionine sulfoxide)

HMDB0002005
     RDKit          3D
Methionine sulfoxide
 21 20  0  0  0  0  0  0  0  0999 V2000
    3.3419   -0.3882    0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6547   -0.6708    0.2572 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.4267   -1.9791   -0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9224    0.7273   -0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.4930   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3102    0.2136    0.2766 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7349   -0.9661    0.8927 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7293    0.0009    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2824   -1.0837    0.3086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160    0.9766   -0.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    0.6935    0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0641   -0.8159    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266   -0.8473    1.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032    1.0327   -1.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9762    1.5937    0.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232    1.3797   -1.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6219   -0.3701   -1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618    1.0814    0.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864   -1.7915    0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -1.0219    1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8808    1.7419   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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  1
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

PDB for NP0000509 (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
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3D PDB for NP0000509 (Methionine sulfoxide)

COMPND    HMDB0002005
HETATM    1  C1  UNL     1       3.342  -0.388   0.728  1.00  0.00           C  
HETATM    2  S1  UNL     1       1.655  -0.671   0.257  1.00  0.00           S  
HETATM    3  O1  UNL     1       1.427  -1.979  -0.446  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.922   0.727  -0.581  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.500   0.493  -0.980  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.310   0.214   0.277  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.735  -0.966   0.893  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.729   0.001   0.010  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.282  -1.084   0.309  1.00  0.00           O  
HETATM   10  O3  UNL     1      -3.516   0.977  -0.576  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.568   0.694   0.798  1.00  0.00           H  
HETATM   12  H2  UNL     1       4.064  -0.816   0.000  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.527  -0.847   1.728  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.503   1.033  -1.494  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.976   1.594   0.110  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.923   1.380  -1.476  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.622  -0.370  -1.638  1.00  0.00           H  
HETATM   18  H8  UNL     1      -1.162   1.081   0.973  1.00  0.00           H  
HETATM   19  H9  UNL     1      -1.186  -1.791   0.396  1.00  0.00           H  
HETATM   20  H10 UNL     1      -1.137  -1.022   1.873  1.00  0.00           H  
HETATM   21  H11 UNL     1      -3.881   1.742  -0.013  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7    8   18
CONECT    7   19   20
CONECT    8    9    9   10
CONECT   10   21
END
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SMILES for NP0000509 (Methionine sulfoxide)

CS(=O)CC[C@H](N)C(O)=O
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INCHI for NP0000509 (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
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View in JSmol
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, MeSH
Chemical FormulaC5H11NO3S
Average Mass165.2100 Da
Monoisotopic Mass165.04596 Da
IUPAC Name(2S)-2-amino-4-methanesulfinylbutanoic acid
Traditional NameL-methionine sulfoxide
CAS Registry Number62697-73-8
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Daphnia pulexLOTUS Database
Daucus carota ssp. sativusFooDB
    • David M. Alabran, and Ahmed F. Mabrouk. Carrot flavor. Sugars and free nitrogenous compounds in f...
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Species Where Detected
Species NameSourceReference
Bombyx moriKNApSAcK Database
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
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
HMDB IDHMDB0002005
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022789
KNApSAcK IDC00051545
Chemspider ID139840
KEGG Compound IDC02989
BioCyc IDCPD0-1959
BiGG IDNot Available
Wikipedia LinkMethionine sulfoxide
METLIN ID6428
PubChem Compound158980
PDB IDNot Available
ChEBI ID17016
Good Scents IDNot Available
References
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 ]
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