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Showing NP-Card for methionine sulfoximine (NP0274339)

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Record Information
Version2.0
Created at2022-09-08 21:41:47 UTC
Updated at2022-09-08 21:41:47 UTC
NP-MRD IDNP0274339
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethionine sulfoximine
DescriptionMethionine sulfoximine, also known as methionine analog, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). methionine sulfoximine is found in Cnestis polyphylla. Methionine sulfoximine is a very strong basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0274339 (methionine sulfoximine)


  Mrv0541 02241217342D          

 11 10  0  0  0  0            999 V2000
    1.8425   -1.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886   -0.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4184   -1.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3347    0.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4184    0.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425    0.4184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8425    0.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886    0.5022    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074   -0.2509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535    1.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  2  0  0  0  0
M  END
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3D MOL for NP0274339 (methionine sulfoximine)

     RDKit          3D

 23 22  0  0  0  0  0  0  0  0999 V2000
   -2.5030    1.2154   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0240   -0.4987   -0.2031 S   0  0  2  0  0  6  0  0  0  0  0  0
   -2.7027   -1.1823   -1.4252 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102   -1.2025    1.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2722   -0.6293   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    0.0723    0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -0.0680    0.4710 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3474   -1.4669    0.4328 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2930    0.5724   -0.8095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8483   -0.1018   -1.7384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0248    1.9131   -1.0451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5350    1.3008    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816    1.7280    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4303    1.6455   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6451   -1.5457   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392   -0.1211   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0158   -1.6963   -0.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1487   -0.4169    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131    1.1461    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532    0.4555    1.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0049   -1.9749    1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3655   -1.5122    0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3117    2.3676   -0.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  1
  8 21  1  0
  8 22  1  0
 11 23  1  0
M  END
Download

3D SDF for NP0274339 (methionine sulfoximine)


  Mrv0541 02241217342D          

 11 10  0  0  0  0            999 V2000
    1.8425   -1.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886   -0.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4184   -1.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3347    0.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4184    0.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0886   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425    0.4184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8425    0.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0886    0.5022    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074   -0.2509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7535    1.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0274339

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS(=N)(=O)CCC(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)

> <INCHI_KEY>
SXTAYKAGBXMACB-UHFFFAOYSA-N

> <FORMULA>
C5H12N2O3S

> <MOLECULAR_WEIGHT>
180.225

> <EXACT_MASS>
180.05686295

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
17.31236187347113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[imino(methyl)oxo-λ⁶-sulfanyl]butanoic acid

> <ALOGPS_LOGP>
-2.97

> <JCHEM_LOGP>
-4.446533138197991

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8865595865396934

> <JCHEM_PKA_STRONGEST_BASIC>
9.091048462528423

> <JCHEM_POLAR_SURFACE_AREA>
104.23999999999998

> <JCHEM_REFRACTIVITY>
40.216800000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methionine sulfoximine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0274339 (methionine sulfoximine)

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PDB for NP0274339 (methionine sulfoximine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.439  -2.345   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.032  -1.563   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.781  -2.345   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.625   0.156   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.781   0.781   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.032  -0.001   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.439   0.781   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -3.439   1.563   0.000  0.00  0.00           C+0
HETATM    9  S   UNK     0      -2.032   0.937   0.000  0.00  0.00           S+0
HETATM   10  N   UNK     0      -2.814  -0.468   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -1.407   2.345   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2                                                            
CONECT    4    5    9                                                       
CONECT    5    4    6                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    4    8   10   11                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0274339 (methionine sulfoximine)
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SMILES for NP0274339 (methionine sulfoximine)
CS(=N)(=O)CCC(N)C(O)=O
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INCHI for NP0274339 (methionine sulfoximine)
InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
2-Amino-4-(S-methylsulphonimidoyl)butyric acidChEBI
2-Amino-4-(S-methylsulfonimidoyl)butyrateGenerator
2-Amino-4-(S-methylsulfonimidoyl)butyric acidGenerator
2-Amino-4-(S-methylsulphonimidoyl)butyrateGenerator
Methionine sulphoximineGenerator
2-Amino-4-(S-methylsulfonimidoyl)-butanoic acidHMDB
2-Amino-4-(S-methylsulfonimidoyl)butanoic acidHMDB
Butanoic acid, 2-amino-4-(S-methylsulfonimidoyl)- (9ci)HMDB
DL-(3-Amino-3-carboxypropyl) methyl sulfoximineHMDB
DL-Methionine DL-sulfoximineHMDB
DL-Methionine sulfoximineHMDB
DL-Methionine-DL-sulfoximineHMDB
L -S-(3-Amino-3-carboxypropyl)-S-methylsulfoximineHMDB
L-Methionine sulfoximineHMDB
L-Methionine-RS-sulfoximineHMDB
Methionine analogHMDB
S-(3-Amino-3-carboxypropyl)-S-methyl-DL-sulfoximineHMDB
S-(3-Amino-3-carboxypropyl)-S-methylsulfoximine, 9ciHMDB
Chemical FormulaC5H12N2O3S
Average Mass180.2250 Da
Monoisotopic Mass180.05686 Da
IUPAC Name2-amino-4-[imino(methyl)oxo-λ⁶-sulfanyl]butanoic acid
Traditional Namemethionine sulfoximine
CAS Registry NumberNot Available
SMILES
CS(=N)(=O)CCC(N)C(O)=O
InChI Identifier
InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)
InChI KeySXTAYKAGBXMACB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cnestis polyphyllaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • Thia fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Carbo-azosulfone
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Primary amine
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-4.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.24 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity40.22 m³·mol⁻¹ChemAxon
Polarizability17.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029430  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000532  
KNApSAcK IDNot Available
Chemspider ID15302  
KEGG Compound IDC03510  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethionine sulfoximine  
METLIN IDNot Available
PubChem Compound16118  
PDB IDNot Available
ChEBI ID47833  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]