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Showing metabocard for S-(1-Propenyl)-cysteine sulfoxide (HMDB0302221)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 16:05:43 UTC
Update Date2021-09-23 16:05:43 UTC
HMDB IDHMDB0302221
Secondary Accession NumbersNone
Metabolite Identification
Common NameS-(1-Propenyl)-cysteine sulfoxide
DescriptionS-(1-propenyl)-cysteine sulfoxide, also known as prensco, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. S-(1-propenyl)-cysteine sulfoxide is soluble (in water) and a moderately acidic compound (based on its pKa). S-(1-propenyl)-cysteine sulfoxide can be found in a number of food items such as babassu palm, spirulina, elderberry, and cassava, which makes S-(1-propenyl)-cysteine sulfoxide a potential biomarker for the consumption of these food products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0302221 (S-(1-Propenyl)-cysteine sulfoxide)

  Mrv0541 02241212382D          

 11 10  0  0  0  0            999 V2000
    4.6184    1.6164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.6164    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.6164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.8539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.7914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  1 11  1  1  0  0  0
M  END
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3D MOL for HMDB0302221 (S-(1-Propenyl)-cysteine sulfoxide)

HMDB0302221
     RDKit          3D
S-(1-Propenyl)-cysteine sulfoxide
 22 21  0  0  0  0  0  0  0  0999 V2000
   -4.3434   -0.1208   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508    0.1321    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480   -0.5079   -0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226   -0.1897    0.6154 S   0  0  0  0  0  4  0  0  0  0  0  0
   -0.5463    0.9512    1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285    0.2028   -0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1661    0.4874    0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1144    0.7926   -1.0042 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563   -0.6501    0.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9906   -1.0885    1.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8552   -1.2462    0.5043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042   -0.7992    0.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216    0.8258   -0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232   -0.5938   -1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9692    0.8502    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9624   -1.2300   -1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9138   -0.6581   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.1048   -1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411    1.3991    0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7811    0.0400   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6463    1.0599   -1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7620   -0.7615    0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  1
  8 20  1  0
  8 21  1  0
 11 22  1  0
M  END
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3D SDF for HMDB0302221 (S-(1-Propenyl)-cysteine sulfoxide)

  Mrv0541 02241212382D          

 11 10  0  0  0  0            999 V2000
    4.6184    1.6164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.6164    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.6164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    2.8539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.7914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  1 11  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302221

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C\S(=O)C[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2+/t5-,11?/m0/s1

> <INCHI_KEY>
OKYHUOHBRKWCQJ-FTJYXMLISA-N

> <FORMULA>
C6H11NO3S

> <MOLECULAR_WEIGHT>
177.221

> <EXACT_MASS>
177.045963913

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.223530761455088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-[(1E)-prop-1-ene-1-sulfinyl]propanoic acid

> <ALOGPS_LOGP>
-1.82

> <JCHEM_LOGP>
-3.5050341615732736

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8370753162837814

> <JCHEM_PKA_STRONGEST_BASIC>
8.437867218516812

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
43.9634

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-3-[(1E)-prop-1-ene-1-sulfinyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0302221 (S-(1-Propenyl)-cysteine sulfoxide)

HMDB0302221
     RDKit          3D
S-(1-Propenyl)-cysteine sulfoxide
 22 21  0  0  0  0  0  0  0  0999 V2000
   -4.3434   -0.1208   -0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508    0.1321    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9480   -0.5079   -0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226   -0.1897    0.6154 S   0  0  0  0  0  4  0  0  0  0  0  0
   -0.5463    0.9512    1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285    0.2028   -0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1661    0.4874    0.0402 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1144    0.7926   -1.0042 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563   -0.6501    0.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9906   -1.0885    1.7848 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8552   -1.2462    0.5043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042   -0.7992    0.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9216    0.8258   -0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232   -0.5938   -1.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9692    0.8502    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9624   -1.2300   -1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9138   -0.6581   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363    1.1048   -1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0411    1.3991    0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7811    0.0400   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6463    1.0599   -1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7620   -0.7615    0.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  1
  8 20  1  0
  8 21  1  0
 11 22  1  0
M  END
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PDB for HMDB0302221 (S-(1-Propenyl)-cysteine sulfoxide)

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  C   UNK     0       8.621   3.017   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.287   3.787   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       5.954   3.017   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0       5.954   1.477   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.620   3.787   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.286   3.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.953   3.787   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.955   3.787   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.288   3.017   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.955   5.327   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       8.621   1.477   0.000  0.00  0.00           N+0
CONECT    1    2    8   11                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0302221 (S-(1-Propenyl)-cysteine sulfoxide)

COMPND    HMDB0302221
HETATM    1  C1  UNL     1      -4.343  -0.121  -0.550  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.051   0.132   0.141  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.948  -0.508  -0.222  1.00  0.00           C  
HETATM    4  S1  UNL     1      -0.423  -0.190   0.615  1.00  0.00           S  
HETATM    5  O1  UNL     1      -0.546   0.951   1.587  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.829   0.203  -0.613  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.166   0.487   0.040  1.00  0.00           C  
HETATM    8  N1  UNL     1       3.114   0.793  -1.004  1.00  0.00           N  
HETATM    9  C6  UNL     1       2.656  -0.650   0.823  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.991  -1.089   1.785  1.00  0.00           O  
HETATM   11  O3  UNL     1       3.855  -1.246   0.504  1.00  0.00           O  
HETATM   12  H1  UNL     1      -5.004  -0.799   0.046  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.922   0.826  -0.672  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.123  -0.594  -1.527  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.969   0.850   0.967  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.962  -1.230  -1.031  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.914  -0.658  -1.304  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.536   1.105  -1.159  1.00  0.00           H  
HETATM   19  H8  UNL     1       2.041   1.399   0.662  1.00  0.00           H  
HETATM   20  H9  UNL     1       3.781   0.040  -1.203  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.646   1.060  -1.889  1.00  0.00           H  
HETATM   22  H11 UNL     1       4.762  -0.761   0.548  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   15
CONECT    3    4   16
CONECT    4    5    5    6
CONECT    6    7   17   18
CONECT    7    8    9   19
CONECT    8   20   21
CONECT    9   10   10   11
CONECT   11   22
END
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SMILES for HMDB0302221 (S-(1-Propenyl)-cysteine sulfoxide)

C\C=C\S(=O)C[C@H](N)C(O)=O
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INCHI for HMDB0302221 (S-(1-Propenyl)-cysteine sulfoxide)

InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2+/t5-,11?/m0/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(2R)-2-Amino-3-[(1E)-prop-1-ene-1-sulfinyl]propanoateGenerator
(2R)-2-Amino-3-[(1E)-prop-1-ene-1-sulphinyl]propanoateGenerator
(2R)-2-Amino-3-[(1E)-prop-1-ene-1-sulphinyl]propanoic acidGenerator
1-Propenyl-L-cysteine sulfoxideMeSH
1-Propenylcysteine sulfoxideMeSH
PRENCSOMeSH
S-(1-Propenyl)-cysteine sulphoxideGenerator
S-(1-Propenyl)-cysteine sulphoxideGenerator
S-(1-Propenyl)-cysteine sulphoxideGenerator
Chemical FormulaC6H11NO3S
Average Molecular Weight177.221
Monoisotopic Molecular Weight177.045963913
IUPAC Name(2R)-2-amino-3-[(1E)-prop-1-ene-1-sulfinyl]propanoic acid
Traditional Name(2R)-2-amino-3-[(1E)-prop-1-ene-1-sulfinyl]propanoic acid
CAS Registry NumberNot Available
SMILES
C\C=C\S(=O)C[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2-3,5H,4,7H2,1H3,(H,8,9)/b3-2+/t5-,11?/m0/s1
InChI KeyOKYHUOHBRKWCQJ-FTJYXMLISA-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
  • Sulfoxide
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfinyl compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007929
KNApSAcK IDC00001389
Chemspider ID4444557
KEGG Compound IDC08295
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available