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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 12:01:19 UTC

Update Date

2021-09-24 12:01:19 UTC

HMDB ID

HMDB0304734

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Sitostanol-beta

Description

(2S)-4-[(2Z)-2-{[(1S)-1-carboxy-2-hydroxyethyl]imino}ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on (2S)-4-[(2Z)-2-{[(1S)-1-carboxy-2-hydroxyethyl]imino}ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid.

Structure

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

HMDB0304734
     RDKit          3D
Sitostanol-beta
 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.8065   -2.6958   -0.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -2.6656   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -3.7078   -0.8657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -1.5529    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -1.5194    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -0.3903    0.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5082   -0.2051    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410    0.8879    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4860    1.0427    1.0304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    0.1812    0.1602 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9532    0.6811   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -0.0758   -2.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    0.3944    0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5728   -0.2219   -0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0638    1.3245    1.3251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763    0.4607    1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809    0.7745    1.0925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6019    1.2572   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471    0.6065   -1.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414    2.4596   -0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -0.4938    0.9741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045   -4.1827   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239   -2.3187   -0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9503   -0.9222    0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351    1.6234    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -0.8949    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    0.7657   -1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3830    1.7265   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    0.3995   -2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6893    2.1022    1.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8920   -0.1935    2.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200    1.3408    2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911    1.5044    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2891    3.1420   -1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -0.6343    1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 21  4  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  6
 11 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  1
 20 34  1  0
 21 35  1  0
M  END

  Mrv1652304022019523D          

 21 21  0  0  0  0            999 V2000
   -0.4633    0.0390   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -0.9398   -1.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    1.1445    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8524   -0.7395   -0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3393    1.2452   -1.2799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    0.1224   -0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    0.9567    1.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6967   -1.3419    0.4237 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1613   -0.0766   -0.5521 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1492    1.9302    2.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6976   -2.2703   -0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5454   -0.6774   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3112   -0.9787   -1.2522 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2930   -0.2253    1.1327 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1663    2.0943   -0.5677 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2774    1.7129    2.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4924    3.1031    2.6806 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9410   -2.1250    0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2762   -3.3887   -0.8128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7037   -1.7857   -1.0816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6064   -0.0511    0.0797 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2 13  2  0  0  0  0
  3  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  9  5  1  6  0  0  0
  5 15  1  0  0  0  0
  7 10  1  0  0  0  0
  7 14  1  0  0  0  0
  8 11  1  6  0  0  0
  8 14  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 10 16  2  0  0  0  0
 10 17  1  0  0  0  0
 11 18  2  0  0  0  0
 11 19  1  0  0  0  0
 12 20  2  0  0  0  0
 12 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304734

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H](\N=C/C=C1\C[C@H](NC(=C1)C(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O7/c15-5-9(12(20)21)13-2-1-6-3-7(10(16)17)14-8(4-6)11(18)19/h1-3,8-9,14-15H,4-5H2,(H,16,17)(H,18,19)(H,20,21)/b6-1-,13-2-/t8-,9-/m0/s1

> <INCHI_KEY>
FPSPMXPRFYBHKR-UQXOTDKOSA-N

> <FORMULA>
C12H14N2O7

> <MOLECULAR_WEIGHT>
298.251

> <EXACT_MASS>
298.080100799

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.103526645335293

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4E)-4-[(2Z)-2-{[(1S)-1-carboxy-2-hydroxyethyl]imino}ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-4.4464825250609765

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.339762539125597

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5090439158853606

> <JCHEM_PKA_STRONGEST_BASIC>
7.762511363167673

> <JCHEM_POLAR_SURFACE_AREA>
156.52

> <JCHEM_REFRACTIVITY>
69.85600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4E)-4-[(2Z)-2-{[(1S)-1-carboxy-2-hydroxyethyl]imino}ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304734
     RDKit          3D
Sitostanol-beta
 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.8065   -2.6958   -0.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -2.6656   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -3.7078   -0.8657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -1.5529    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -1.5194    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -0.3903    0.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5082   -0.2051    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410    0.8879    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4860    1.0427    1.0304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    0.1812    0.1602 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9532    0.6811   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -0.0758   -2.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    0.3944    0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5728   -0.2219   -0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0638    1.3245    1.3251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763    0.4607    1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809    0.7745    1.0925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6019    1.2572   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471    0.6065   -1.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414    2.4596   -0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -0.4938    0.9741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045   -4.1827   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239   -2.3187   -0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9503   -0.9222    0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351    1.6234    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -0.8949    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    0.7657   -1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3830    1.7265   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    0.3995   -2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6893    2.1022    1.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8920   -0.1935    2.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200    1.3408    2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911    1.5044    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2891    3.1420   -1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -0.6343    1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 21  4  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  6
 11 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  1
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      -0.463   0.039  -0.221  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.040  -0.940  -1.109  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.398   1.145   0.887  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.852  -0.740  -0.694  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.339   1.245  -1.280  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.849   0.122  -0.037  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.580   0.957   1.438  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.697  -1.342   0.424  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.161  -0.077  -0.552  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.149   1.930   2.344  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.698  -2.270  -0.109  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.545  -0.677  -0.525  0.00  0.00           C+0
HETATM   13  N   UNK     0      -2.311  -0.979  -1.252  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.293  -0.225   1.133  0.00  0.00           N+0
HETATM   15  O   UNK     0      -4.166   2.094  -0.568  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.277   1.713   2.846  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.492   3.103   2.681  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.941  -2.125   0.027  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.276  -3.389  -0.813  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.704  -1.786  -1.082  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.606  -0.051   0.080  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1   13                                                       
CONECT    3    6    7                                                       
CONECT    4    6    8                                                       
CONECT    5    9   15                                                       
CONECT    6    1    3    4                                                  
CONECT    7    3   10   14                                                  
CONECT    8    4   11   14                                                  
CONECT    9    5   12   13                                                  
CONECT   10    7   16   17                                                  
CONECT   11    8   18   19                                                  
CONECT   12    9   20   21                                                  
CONECT   13    2    9                                                       
CONECT   14    7    8                                                       
CONECT   15    5                                                            
CONECT   16   10                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   12                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0304734
HETATM    1  O1  UNL     1      -4.807  -2.696  -0.241  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.566  -2.666  -0.257  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.884  -3.708  -0.866  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.836  -1.553   0.354  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.512  -1.519   0.338  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.778  -0.390   0.959  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.508  -0.205   0.703  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.241   0.888   1.297  1.00  0.00           C  
HETATM    9  N1  UNL     1       2.486   1.043   1.030  1.00  0.00           N  
HETATM   10  C7  UNL     1       3.217   0.181   0.160  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.953   0.681  -1.269  1.00  0.00           C  
HETATM   12  O3  UNL     1       3.608  -0.076  -2.210  1.00  0.00           O  
HETATM   13  C9  UNL     1       4.669   0.394   0.381  1.00  0.00           C  
HETATM   14  O4  UNL     1       5.573  -0.222  -0.240  1.00  0.00           O  
HETATM   15  O5  UNL     1       5.064   1.325   1.325  1.00  0.00           O  
HETATM   16  C10 UNL     1      -1.576   0.461   1.841  1.00  0.00           C  
HETATM   17  C11 UNL     1      -2.881   0.775   1.093  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.602   1.257  -0.281  1.00  0.00           C  
HETATM   19  O6  UNL     1      -2.947   0.607  -1.297  1.00  0.00           O  
HETATM   20  O7  UNL     1      -1.941   2.460  -0.486  1.00  0.00           O  
HETATM   21  N2  UNL     1      -3.574  -0.494   0.974  1.00  0.00           N  
HETATM   22  H1  UNL     1      -3.205  -4.183  -1.684  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.924  -2.319  -0.131  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.950  -0.922   0.030  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.835   1.623   1.973  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.954  -0.895   0.246  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.875   0.766  -1.388  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.383   1.727  -1.269  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.374   0.399  -2.594  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.689   2.102   1.078  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.892  -0.193   2.708  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.120   1.341   2.255  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.491   1.504   1.664  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.289   3.142  -1.162  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.556  -0.634   1.319  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   22
CONECT    4    5    5   21
CONECT    5    6   23
CONECT    6    7    7   16
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10
CONECT   10   11   13   26
CONECT   11   12   27   28
CONECT   12   29
CONECT   13   14   14   15
CONECT   15   30
CONECT   16   17   31   32
CONECT   17   18   21   33
CONECT   18   19   19   20
CONECT   20   34
CONECT   21   35
END

HMDB0304734
     RDKit          3D
Sitostanol-beta
 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.8065   -2.6958   -0.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -2.6656   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8840   -3.7078   -0.8657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8364   -1.5529    0.3545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5117   -1.5194    0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7780   -0.3903    0.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5082   -0.2051    0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410    0.8879    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4860    1.0427    1.0304 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    0.1812    0.1602 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9532    0.6811   -1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -0.0758   -2.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    0.3944    0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5728   -0.2219   -0.2400 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0638    1.3245    1.3251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763    0.4607    1.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809    0.7745    1.0925 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6019    1.2572   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471    0.6065   -1.2971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414    2.4596   -0.4858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5741   -0.4938    0.9741 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045   -4.1827   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9239   -2.3187   -0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9503   -0.9222    0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351    1.6234    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -0.8949    0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    0.7657   -1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3830    1.7265   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    0.3995   -2.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6893    2.1022    1.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8920   -0.1935    2.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200    1.3408    2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4911    1.5044    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2891    3.1420   -1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -0.6343    1.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 21  4  1  0
  3 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  6
 11 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 17 33  1  1
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S)-4-[(2Z)-2-{[(1S)-1-carboxy-2-hydroxyethyl]imino}ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylate	Generator

Chemical Formula

C₁₂H₁₄N₂O₇

Average Molecular Weight

298.251

Monoisotopic Molecular Weight

298.080100799

IUPAC Name

(2S,4E)-4-[(2Z)-2-{[(1S)-1-carboxy-2-hydroxyethyl]imino}ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

Traditional Name

(2S,4E)-4-[(2Z)-2-{[(1S)-1-carboxy-2-hydroxyethyl]imino}ethylidene]-2,3-dihydro-1H-pyridine-2,6-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

OC[C@H](\N=C/C=C1\C[C@H](NC(=C1)C(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C12H14N2O7/c15-5-9(12(20)21)13-2-1-6-3-7(10(16)17)14-8(4-6)11(18)19/h1-3,8-9,14-15H,4-5H2,(H,16,17)(H,18,19)(H,20,21)/b6-1-,13-2-/t8-,9-/m0/s1

InChI Key

FPSPMXPRFYBHKR-UQXOTDKOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serine and derivatives. Serine and derivatives are compounds containing serine or a derivative thereof resulting from reaction of serine 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

Serine and derivatives

Alternative Parents

Substituents

Serine or derivatives
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Tetrahydropyridine
Hydropyridine
Hydroxy acid
Amino acid
Shiff base
Aldimine
Carboxylic acid
Secondary aliphatic amine
Enamine
Secondary amine
Azacycle
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Imine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary alcohol
Amine
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0304734)

Celeriac (FooDB: FOOD00214)

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Cocoa and cocoa product

Cocoa product

Chocolate (FooDB: FOOD00687)

Herb and spice

Oilseed crop

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cereal and cereal product

Cereal

Common wheat (FooDB: FOOD00187)

Process

Not Available

Role

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	-0.2	ALOGPS
logP	-4.4	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	7.76	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	69.86 m³·mol⁻¹	ChemAxon
Polarizability	28.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	165.598	32859911
AllCCS	[M+H-H2O]+	162.412	32859911
AllCCS	[M+Na]+	169.395	32859911
AllCCS	[M+NH4]+	168.548	32859911
AllCCS	[M-H]-	163.729	32859911
AllCCS	[M+Na-2H]-	163.662	32859911
AllCCS	[M+HCOO]-	163.707	32859911
DeepCCS	[M+H]+	165.127	30932474
DeepCCS	[M-H]-	162.769	30932474
DeepCCS	[M-2H]-	196.893	30932474
DeepCCS	[M+Na]+	172.812	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sitostanol-beta,5TMS,isomer #1	C[Si](C)(C)OC[C@H](/N=C\C=C1\C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[C@H](C(=O)O[Si](C)(C)C)C1)C(=O)O[Si](C)(C)C	2706.2	Semi standard non polar	33892256
Sitostanol-beta,5TMS,isomer #1	C[Si](C)(C)OC[C@H](/N=C\C=C1\C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[C@H](C(=O)O[Si](C)(C)C)C1)C(=O)O[Si](C)(C)C	2540.0	Standard non polar	33892256
Sitostanol-beta,5TMS,isomer #1	C[Si](C)(C)OC[C@H](/N=C\C=C1\C=C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[C@H](C(=O)O[Si](C)(C)C)C1)C(=O)O[Si](C)(C)C	3209.6	Standard polar	33892256
Sitostanol-beta,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](/N=C\C=C1\C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C1)C(=O)O[Si](C)(C)C(C)(C)C	3706.7	Semi standard non polar	33892256
Sitostanol-beta,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](/N=C\C=C1\C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C1)C(=O)O[Si](C)(C)C(C)(C)C	3229.5	Standard non polar	33892256
Sitostanol-beta,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](/N=C\C=C1\C=C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C1)C(=O)O[Si](C)(C)C(C)(C)C	3492.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sitostanol-beta GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-1490000000-3c22140d1da3272c6dae	2017-07-27	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 10V, Positive-QTOF	splash10-0f7k-0190000000-891cbd6568bec5ec9b09	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 20V, Positive-QTOF	splash10-0udu-1980000000-84bfd80483a537025549	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 40V, Positive-QTOF	splash10-052r-5930000000-6899a678a46288a97242	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 10V, Negative-QTOF	splash10-0f6t-0190000000-8d6fa0ac7f6c09bd8f64	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 20V, Negative-QTOF	splash10-0zmr-0190000000-52c1e495957c560b455e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 40V, Negative-QTOF	splash10-0pi0-9410000000-bd3e0864b1ae42728950	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 10V, Positive-QTOF	splash10-0002-0090000000-f94d809317c83eb11226	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 20V, Positive-QTOF	splash10-0uki-0390000000-27f44964e64ba1f824c1	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 40V, Positive-QTOF	splash10-0frb-0930000000-588eea5836c73c8daceb	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 10V, Negative-QTOF	splash10-0uds-0090000000-98f872aceeb68d83c8dc	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 20V, Negative-QTOF	splash10-000i-0960000000-c3de269174be36a285bd	2021-10-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sitostanol-beta 40V, Negative-QTOF	splash10-0k9i-1940000000-9fa3e1af1874be0ad36e	2021-10-22	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

FDB097360

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 Sitostanol-beta (HMDB0304734)

MOL for HMDB0304734 (Sitostanol-beta)

3D MOL for HMDB0304734 (Sitostanol-beta)

3D SDF for HMDB0304734 (Sitostanol-beta)

3D-SDF for HMDB0304734 (Sitostanol-beta)

PDB for HMDB0304734 (Sitostanol-beta)

3D PDB for HMDB0304734 (Sitostanol-beta)

SMILES for HMDB0304734 (Sitostanol-beta)

INCHI for HMDB0304734 (Sitostanol-beta)

Structure for HMDB0304734 (Sitostanol-beta)

3D Structure for HMDB0304734 (Sitostanol-beta)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra