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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 07:47:23 UTC

Update Date

2021-09-24 07:47:23 UTC

HMDB ID

HMDB0304176

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-hydroxy-2-nonenal-[L-Cys] conjugate

Description

4-hydroxy-2-nonenal-[l-cys] conjugate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 4-hydroxy-2-nonenal-[l-cys] conjugate can be found in a number of food items such as ginkgo nuts, sweet orange, taro, and black crowberry, which makes 4-hydroxy-2-nonenal-[l-cys] conjugate a potential biomarker for the consumption of these food products.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0304176
     RDKit          3D
4-hydroxy-2-nonenal-[L-Cys] conjugate
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.6877    0.7366    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -0.2798   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -0.7424    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770    0.4209    0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076   -0.0312    1.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -1.0433    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -1.4045    1.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.5666   -0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.5251   -1.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9823   -2.8190   -1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521   -3.0972   -1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5378    1.0413   -0.6083 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0919    0.8856    0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024    2.2214    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417    3.1748    1.0762 N   0  0  0  0  0  1  0  0  0  0  0  0
   -4.0953    2.7614   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    2.2999   -2.0146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9434    3.8566   -1.0315 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.6833    0.4696    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    1.7722   -0.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212    0.6873   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4956    0.1507   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5016   -1.1381   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466   -1.5201   -0.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -1.1980    1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923    1.1466    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    0.9397   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514    0.8362    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0454   -0.5559    2.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936   -1.9394    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -1.7459    2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2050   -0.3944   -1.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815   -1.6973   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -1.0668   -2.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697   -3.5511   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    0.1860   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158    0.5688    1.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7466    2.1603    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
M  CHG  2  15   1  18  -1
M  RAD  1  15   2
M  END


  Mrv1533005141521402D          

 18 17  0  0  0  0            999 V2000
    3.5211    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    1.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    4.0954    0.0000 N   0  3  0  0  0  1  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  5  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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  CHG  2  15   1  18  -1
M  RAD  1  15   2
M  END
> <DATABASE_ID>
HMDB0304176

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(O)C(CC=O)SCC([N+])C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO4S/c1-2-3-4-5-10(15)11(6-7-14)18-8-9(13)12(16)17/h7,9-11,15H,2-6,8H2,1H3,(H,16,17)/q+1/p-1

> <INCHI_KEY>
XJUXNVLIARNBIH-UHFFFAOYSA-M

> <FORMULA>
C12H20NO4S

> <MOLECULAR_WEIGHT>
274.36

> <EXACT_MASS>
274.111304302

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.975908980023593

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{1-carboxylato-2-[(4-hydroxy-1-oxononan-3-yl)sulfanyl]ethyl}azaniumyl

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-0.12209822320927818

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.479823301592454

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9524394918603711

> <JCHEM_PKA_STRONGEST_BASIC>
-2.974955149226732

> <JCHEM_POLAR_SURFACE_AREA>
100.49000000000001

> <JCHEM_REFRACTIVITY>
80.9319

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{1-carboxylato-2-[(4-hydroxy-1-oxononan-3-yl)sulfanyl]ethyl}ammonio

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304176
     RDKit          3D
4-hydroxy-2-nonenal-[L-Cys] conjugate
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.6877    0.7366    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -0.2798   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -0.7424    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770    0.4209    0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076   -0.0312    1.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -1.0433    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -1.4045    1.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.5666   -0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.5251   -1.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9823   -2.8190   -1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521   -3.0972   -1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5378    1.0413   -0.6083 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0919    0.8856    0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024    2.2214    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417    3.1748    1.0762 N   0  0  0  0  0  1  0  0  0  0  0  0
   -4.0953    2.7614   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    2.2999   -2.0146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9434    3.8566   -1.0315 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.6833    0.4696    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    1.7722   -0.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212    0.6873   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4956    0.1507   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5016   -1.1381   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466   -1.5201   -0.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -1.1980    1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923    1.1466    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    0.9397   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514    0.8362    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0454   -0.5559    2.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936   -1.9394    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -1.7459    2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2050   -0.3944   -1.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815   -1.6973   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -1.0668   -2.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697   -3.5511   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    0.1860   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158    0.5688    1.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7466    2.1603    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
M  CHG  2  15   1  18  -1
M  RAD  1  15   2
M  END

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0       6.573   5.335   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.906   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.574   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.241   6.105   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.241   7.645   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.575   3.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.908   3.025   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.908   1.485   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0      15.908   6.105   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      18.576   7.645   0.000  0.00  0.00           N+1
HETATM   16  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0304176
HETATM    1  C1  UNL     1       4.688   0.737   0.059  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.848  -0.280  -0.681  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.676  -0.742   0.161  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.777   0.421   0.529  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.608  -0.031   1.367  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.251  -1.043   0.642  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.300  -1.404   1.472  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.714  -0.567  -0.691  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.565  -1.525  -1.438  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.982  -2.819  -1.767  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.152  -3.097  -1.457  1.00  0.00           O  
HETATM   12  S1  UNL     1      -1.538   1.041  -0.608  1.00  0.00           S  
HETATM   13  C10 UNL     1      -3.092   0.886   0.323  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.802   2.221   0.405  1.00  0.00           C  
HETATM   15  N1  UNL     1      -2.942   3.175   1.076  1.00  0.00           N1+
HETATM   16  C12 UNL     1      -4.095   2.761  -0.944  1.00  0.00           C  
HETATM   17  O3  UNL     1      -3.632   2.300  -2.015  1.00  0.00           O  
HETATM   18  O4  UNL     1      -4.943   3.857  -1.032  1.00  0.00           O1-
HETATM   19  H1  UNL     1       4.683   0.470   1.135  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.290   1.772  -0.116  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.721   0.687  -0.297  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.496   0.151  -1.622  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.502  -1.138  -0.911  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.147  -1.520  -0.421  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.032  -1.198   1.104  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.392   1.147   1.100  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.449   0.940  -0.400  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.051   0.836   1.733  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.045  -0.556   2.258  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.394  -1.939   0.531  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.979  -1.746   2.332  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.205  -0.394  -1.329  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.482  -1.697  -0.832  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.918  -1.067  -2.407  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.570  -3.551  -2.300  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.788   0.186  -0.178  1.00  0.00           H  
HETATM   37  H19 UNL     1      -2.816   0.569   1.350  1.00  0.00           H  
HETATM   38  H20 UNL     1      -4.747   2.160   0.959  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7    8   30
CONECT    7   31
CONECT    8    9   12   32
CONECT    9   10   33   34
CONECT   10   11   11   35
CONECT   12   13
CONECT   13   14   36   37
CONECT   14   15   16   38
CONECT   16   17   17   18
END

HMDB0304176
     RDKit          3D
4-hydroxy-2-nonenal-[L-Cys] conjugate
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.6877    0.7366    0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -0.2798   -0.6813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763   -0.7424    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770    0.4209    0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076   -0.0312    1.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -1.0433    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -1.4045    1.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.5666   -0.6912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.5251   -1.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9823   -2.8190   -1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521   -3.0972   -1.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5378    1.0413   -0.6083 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0919    0.8856    0.3228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8024    2.2214    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417    3.1748    1.0762 N   0  0  0  0  0  1  0  0  0  0  0  0
   -4.0953    2.7614   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    2.2999   -2.0146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9434    3.8566   -1.0315 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.6833    0.4696    1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2896    1.7722   -0.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212    0.6873   -0.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4956    0.1507   -1.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5016   -1.1381   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466   -1.5201   -0.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -1.1980    1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3923    1.1466    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495    0.9397   -0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514    0.8362    1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0454   -0.5559    2.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936   -1.9394    0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792   -1.7459    2.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2050   -0.3944   -1.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4815   -1.6973   -0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -1.0668   -2.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5697   -3.5511   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7875    0.1860   -0.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8158    0.5688    1.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7466    2.1603    0.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
M  CHG  2  15   1  18  -1
M  RAD  1  15   2
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-2-nonenal-[L-cys] conjugic acid	Generator

Chemical Formula

C₁₂H₂₀NO₄S

Average Molecular Weight

274.36

Monoisotopic Molecular Weight

274.111304302

IUPAC Name

{1-carboxylato-2-[(4-hydroxy-1-oxononan-3-yl)sulfanyl]ethyl}azaniumyl

Traditional Name

{1-carboxylato-2-[(4-hydroxy-1-oxononan-3-yl)sulfanyl]ethyl}ammonio

CAS Registry Number

Not Available

SMILES

CCCCCC(O)C(CC=O)SCC([N+])C([O-])=O

InChI Identifier

InChI=1S/C12H21NO4S/c1-2-3-4-5-10(15)11(6-7-14)18-8-9(13)12(16)17/h7,9-11,15H,2-6,8H2,1H3,(H,16,17)/q+1/p-1

InChI Key

XJUXNVLIARNBIH-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
Thia fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Alpha-hydrogen aldehyde
Secondary alcohol
Carboxylic acid salt
Dialkylthioether
Sulfenyl compound
Thioether
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.54	ALOGPS
logP	-0.12	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	1.95	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.49 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	80.93 m³·mol⁻¹	ChemAxon
Polarizability	28.98 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	162.708	32859911
AllCCS	[M+H-H2O]+	159.724	32859911
AllCCS	[M+Na]+	166.263	32859911
AllCCS	[M+NH4]+	165.47	32859911
AllCCS	[M-H]-	165.03	32859911
AllCCS	[M+Na-2H]-	165.552	32859911
AllCCS	[M+HCOO]-	166.244	32859911
DeepCCS	[M+H]+	160.456	30932474
DeepCCS	[M-H]-	157.004	30932474
DeepCCS	[M-2H]-	192.347	30932474
DeepCCS	[M+Na]+	168.638	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(CC=O)SCC([N+])C(=O)[O-]	2174.8	Semi standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(CC=O)SCC([N+])C(=O)[O-]	2120.4	Standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(CC=O)SCC([N+])C(=O)[O-]	2795.2	Standard polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TMS,isomer #2	CCCCCC(O)C(C=CO[Si](C)(C)C)SCC([N+])C(=O)[O-]	2277.0	Semi standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TMS,isomer #2	CCCCCC(O)C(C=CO[Si](C)(C)C)SCC([N+])C(=O)[O-]	2152.6	Standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TMS,isomer #2	CCCCCC(O)C(C=CO[Si](C)(C)C)SCC([N+])C(=O)[O-]	2947.0	Standard polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,2TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(C=CO[Si](C)(C)C)SCC([N+])C(=O)[O-]	2310.5	Semi standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,2TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(C=CO[Si](C)(C)C)SCC([N+])C(=O)[O-]	2240.4	Standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,2TMS,isomer #1	CCCCCC(O[Si](C)(C)C)C(C=CO[Si](C)(C)C)SCC([N+])C(=O)[O-]	2694.3	Standard polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(CC=O)SCC([N+])C(=O)[O-]	2422.4	Semi standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(CC=O)SCC([N+])C(=O)[O-]	2327.2	Standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(CC=O)SCC([N+])C(=O)[O-]	2877.9	Standard polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TBDMS,isomer #2	CCCCCC(O)C(C=CO[Si](C)(C)C(C)(C)C)SCC([N+])C(=O)[O-]	2499.5	Semi standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TBDMS,isomer #2	CCCCCC(O)C(C=CO[Si](C)(C)C(C)(C)C)SCC([N+])C(=O)[O-]	2370.5	Standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,1TBDMS,isomer #2	CCCCCC(O)C(C=CO[Si](C)(C)C(C)(C)C)SCC([N+])C(=O)[O-]	3024.0	Standard polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,2TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(C=CO[Si](C)(C)C(C)(C)C)SCC([N+])C(=O)[O-]	2757.6	Semi standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,2TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(C=CO[Si](C)(C)C(C)(C)C)SCC([N+])C(=O)[O-]	2666.2	Standard non polar	33892256
4-hydroxy-2-nonenal-[L-Cys] conjugate,2TBDMS,isomer #1	CCCCCC(O[Si](C)(C)C(C)(C)C)C(C=CO[Si](C)(C)C(C)(C)C)SCC([N+])C(=O)[O-]	2864.8	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-2-nonenal-[L-Cys] conjugate 10V, Positive-QTOF	splash10-03di-1290000000-5ea8ffbb0c40b55c6584	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-2-nonenal-[L-Cys] conjugate 20V, Positive-QTOF	splash10-0006-9210000000-43aaecd701be2c3cbc34	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-2-nonenal-[L-Cys] conjugate 40V, Positive-QTOF	splash10-00di-9200000000-475b49c21aa0600f8867	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-2-nonenal-[L-Cys] conjugate 10V, Negative-QTOF	splash10-0a4i-1390000000-438b9d740f72fb58671d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-2-nonenal-[L-Cys] conjugate 20V, Negative-QTOF	splash10-0079-4930000000-f84fdc65cbd8b7e6c047	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-2-nonenal-[L-Cys] conjugate 40V, Negative-QTOF	splash10-000f-9200000000-eb8f75742f7c9135358e	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030497

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 4-hydroxy-2-nonenal-[L-Cys] conjugate (HMDB0304176)

MOL for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

3D MOL for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

3D SDF for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

3D-SDF for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

PDB for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

3D PDB for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

SMILES for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

INCHI for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

Structure for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

3D Structure for HMDB0304176 (4-hydroxy-2-nonenal-[L-Cys] conjugate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra