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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:06 UTC

Update Date

2022-03-07 02:52:08 UTC

HMDB ID

HMDB0029386

Secondary Accession Numbers

HMDB29386

Metabolite Identification

Common Name

Indicaxanthin

Description

Indicaxanthin belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline 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 a significant number of articles have been published on Indicaxanthin.

Structure

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

HMDB0029386
     RDKit          3D
Indicaxanthin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.0016   -3.5207   -0.9468 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -2.3762   -0.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7291   -2.1466   -0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -1.2963   -0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -1.5452   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502   -0.4740   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -0.7485   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    0.3358   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648    0.0397   -0.2520 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.9423   -1.2583   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2773   -1.1558    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386    0.2352    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.9777   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2117    1.1422   -1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    0.5439   -1.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7130    2.0106   -2.3147 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.5311    0.9380   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    1.1798   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3393    2.2800    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036    2.1820    1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622    3.4819    0.4779 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    0.0131   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1339   -2.6016    0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123   -2.5337   -0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408   -1.7675   -0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683    1.3746   -0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.0942    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1947   -1.4427   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1181   -1.4000   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2835   -1.8580    1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8429    0.2631    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    0.6742    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1088    1.9523    0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439    1.2997    0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0356    1.5191   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050    1.5499   -1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557    4.1043   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6991    0.1223    0.4902 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
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22  4  1  0
 13  9  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 22 38  1  0
M  CHG  2   9   1  16  -1
M  END

  Mrv0541 02241218542D          

 22 23  0  0  0  0            999 V2000
   -0.3551   -0.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1461   -0.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3828   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1739   -1.4229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    0.0782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3828    0.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925    1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0397    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7506    0.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3042   -0.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -0.8694    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.2764   -1.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -2.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409   -1.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3320   -1.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267   -2.2132    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.7267    1.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9365    1.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6990    2.2132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267   -0.7907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9881   -2.0552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3 22  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 15  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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  2  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
M  CHG  2  11   1  17  -1
M  END
> <DATABASE_ID>
HMDB0029386

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1C\C(=C/C=[N+]2\CCCC2C([O-])=O)C=C(N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16N2O6/c17-12(18)9-6-8(7-10(15-9)13(19)20)3-5-16-4-1-2-11(16)14(21)22/h3,5-6,10-11H,1-2,4,7H2,(H3,17,18,19,20,21,22)

> <INCHI_KEY>
RJIIQBYZGJSODH-UHFFFAOYSA-N

> <FORMULA>
C14H16N2O6

> <MOLECULAR_WEIGHT>
308.2866

> <EXACT_MASS>
308.100836254

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
29.591575704560043

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1λ⁵-pyrrolidin-1-ylium-2-carboxylate

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-4.120196724471745

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6996592335930973

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1199313711687036

> <JCHEM_PKA_STRONGEST_BASIC>
0.08164305732449473

> <JCHEM_POLAR_SURFACE_AREA>
129.77

> <JCHEM_REFRACTIVITY>
98.05339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E)-1-{2-[(4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-1λ⁵-pyrrolidin-1-ylium-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029386
     RDKit          3D
Indicaxanthin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.0016   -3.5207   -0.9468 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -2.3762   -0.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7291   -2.1466   -0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -1.2963   -0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -1.5452   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502   -0.4740   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -0.7485   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    0.3358   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648    0.0397   -0.2520 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.9423   -1.2583   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2773   -1.1558    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386    0.2352    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.9777   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2117    1.1422   -1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    0.5439   -1.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7130    2.0106   -2.3147 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.5311    0.9380   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    1.1798   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3393    2.2800    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036    2.1820    1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622    3.4819    0.4779 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    0.0131   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1339   -2.6016    0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123   -2.5337   -0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408   -1.7675   -0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683    1.3746   -0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.0942    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1947   -1.4427   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1181   -1.4000   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2835   -1.8580    1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8429    0.2631    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    0.6742    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1088    1.9523    0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439    1.2997    0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0356    1.5191   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050    1.5499   -1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557    4.1043   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6991    0.1223    0.4902 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
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22  4  1  0
 13  9  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 22 38  1  0
M  CHG  2   9   1  16  -1
M  END

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      -0.663  -0.592   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.139  -1.033   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.581  -2.508   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.058  -2.656   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -3.171   0.146   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.581   1.474   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.106   1.918   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.074   0.736   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.401   1.031   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.435  -0.149   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.991  -1.623   0.000  0.00  0.00           N+1
HETATM   12  C   UNK     0       0.516  -2.066   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.516  -3.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.991  -3.985   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.876  -2.804   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.353  -2.804   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.090  -4.131   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      -5.090   2.360   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.615   2.655   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.171   4.131   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.090  -1.476   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.844  -3.836   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    5                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    1    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   11   14   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16                                                            
CONECT   18   19                                                            
CONECT   19    6   18   20                                                  
CONECT   20   19                                                            
CONECT   21   16                                                            
CONECT   22    3                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0029386
HETATM    1  O1  UNL     1       4.002  -3.521  -0.947  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.377  -2.376  -0.600  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.729  -2.147  -0.392  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.404  -1.296  -0.416  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.122  -1.545  -0.621  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.150  -0.474  -0.439  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.163  -0.749  -0.435  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.125   0.336  -0.252  1.00  0.00           C  
HETATM    9  N1  UNL     1      -2.365   0.040  -0.252  1.00  0.00           N1+
HETATM   10  C7  UNL     1      -2.942  -1.258  -0.414  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.277  -1.156   0.332  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.339   0.235   0.880  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.443   0.978  -0.090  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.212   1.142  -1.355  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.281   0.544  -1.602  1.00  0.00           O  
HETATM   16  O4  UNL     1      -3.713   2.011  -2.315  1.00  0.00           O1-
HETATM   17  C12 UNL     1       1.531   0.938  -0.253  1.00  0.00           C  
HETATM   18  C13 UNL     1       2.998   1.180  -0.323  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.339   2.280   0.615  1.00  0.00           C  
HETATM   20  O5  UNL     1       4.204   2.182   1.520  1.00  0.00           O  
HETATM   21  O6  UNL     1       2.662   3.482   0.478  1.00  0.00           O  
HETATM   22  N2  UNL     1       3.808   0.013  -0.021  1.00  0.00           N  
HETATM   23  H1  UNL     1       6.134  -2.602   0.428  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.812  -2.534  -0.919  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.441  -1.768  -0.570  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.768   1.375  -0.118  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.344  -2.094   0.009  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.195  -1.443  -1.486  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.118  -1.400  -0.315  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.284  -1.858   1.188  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.843   0.263   1.877  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.350   0.674   0.885  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.109   1.952   0.316  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.144   1.300   0.710  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.036   1.519  -1.057  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.305   1.550  -1.343  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.856   4.104  -0.304  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.699   0.122   0.490  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5    5   22
CONECT    5    6   24
CONECT    6    7    7   17
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10   13
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   33
CONECT   14   15   15   16
CONECT   17   18   34   35
CONECT   18   19   22   36
CONECT   19   20   20   21
CONECT   21   37
CONECT   22   38
END

HMDB0029386
     RDKit          3D
Indicaxanthin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.0016   -3.5207   -0.9468 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -2.3762   -0.5998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7291   -2.1466   -0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4038   -1.2963   -0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1221   -1.5452   -0.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1502   -0.4740   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631   -0.7485   -0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    0.3358   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648    0.0397   -0.2520 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.9423   -1.2583   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2773   -1.1558    0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386    0.2352    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.9777   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2117    1.1422   -1.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    0.5439   -1.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7130    2.0106   -2.3147 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.5311    0.9380   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9975    1.1798   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3393    2.2800    0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2036    2.1820    1.5201 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6622    3.4819    0.4779 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    0.0131   -0.0214 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1339   -2.6016    0.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8123   -2.5337   -0.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408   -1.7675   -0.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683    1.3746   -0.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.0942    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1947   -1.4427   -1.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1181   -1.4000   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2835   -1.8580    1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8429    0.2631    1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3502    0.6742    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1088    1.9523    0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1439    1.2997    0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0356    1.5191   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3050    1.5499   -1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557    4.1043   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6991    0.1223    0.4902 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
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22  4  1  0
 13  9  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 22 38  1  0
M  CHG  2   9   1  16  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-[2-(2-Carboxy-1-pyrrolidinyl)ethenyl]-2,3-dihydro-2,6-pyridinedicarboxylic acid, 9ci	HMDB

Chemical Formula

C₁₄H₁₆N₂O₆

Average Molecular Weight

308.2866

Monoisotopic Molecular Weight

308.100836254

IUPAC Name

(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1λ⁵-pyrrolidin-1-ylium-2-carboxylate

Traditional Name

(1E)-1-{2-[(4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-1λ⁵-pyrrolidin-1-ylium-2-carboxylate

CAS Registry Number

2181-75-1

SMILES

OC(=O)C1C\C(=C/C=[N+]2\CCCC2C([O-])=O)C=C(N1)C(O)=O

InChI Identifier

InChI=1S/C14H16N2O6/c17-12(18)9-6-8(7-10(15-9)13(19)20)3-5-16-4-1-2-11(16)14(21)22/h3,5-6,10-11H,1-2,4,7H2,(H3,17,18,19,20,21,22)

InChI Key

RJIIQBYZGJSODH-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
Tricarboxylic acid or derivatives
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Tetrahydropyridine
Hydropyridine
Pyrrolidine
Carboxylic acid salt
Amino acid
Shiff base
Carboxylic acid
Secondary aliphatic amine
Enamine
Azacycle
Secondary amine
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic salt
Organic nitrogen compound
Organic zwitterion
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029386)
Cytoplasm (HMDB: HMDB0029386)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029386)

Source

Endogenous

Endogenous (HMDB: HMDB0029386)

Plant

Plant (HMDB: HMDB0029386)

Exogenous

Food

Food (HMDB: HMDB0029386)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0029386)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	160 - 162 °C	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
Water Solubility	0.21 g/L	ALOGPS
logP	-1	ALOGPS
logP	-4.1	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	2.12	ChemAxon
pKa (Strongest Basic)	0.082	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	129.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.05 m³·mol⁻¹	ChemAxon
Polarizability	29.59 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	168.876	30932474
DeepCCS	[M-H]-	166.517	30932474
DeepCCS	[M-2H]-	200.315	30932474
DeepCCS	[M+Na]+	176.238	30932474
AllCCS	[M+H]+	167.6	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	170.6	32859911
AllCCS	[M+Na]+	171.5	32859911
AllCCS	[M-H]-	168.0	32859911
AllCCS	[M+Na-2H]-	167.3	32859911
AllCCS	[M+HCOO]-	166.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indicaxanthin	OC(=O)C1C\C(=C/C=[N+]2\CCCC2C([O-])=O)C=C(N1)C(O)=O	4325.6	Standard polar	33892256
Indicaxanthin	OC(=O)C1C\C(=C/C=[N+]2\CCCC2C([O-])=O)C=C(N1)C(O)=O	2387.1	Standard non polar	33892256
Indicaxanthin	OC(=O)C1C\C(=C/C=[N+]2\CCCC2C([O-])=O)C=C(N1)C(O)=O	3145.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indicaxanthin,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1C/C(=C\C=[N+]2/CCCC2C(=O)[O-])C=C(C(=O)O)N1	2895.2	Semi standard non polar	33892256
Indicaxanthin,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O)N1	2877.2	Semi standard non polar	33892256
Indicaxanthin,1TMS,isomer #3	C[Si](C)(C)N1C(C(=O)O)=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC1C(=O)O	2928.6	Semi standard non polar	33892256
Indicaxanthin,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O[Si](C)(C)C)N1	2876.6	Semi standard non polar	33892256
Indicaxanthin,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1C/C(=C\C=[N+]2/CCCC2C(=O)[O-])C=C(C(=O)O)N1[Si](C)(C)C	2886.4	Semi standard non polar	33892256
Indicaxanthin,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O)N1[Si](C)(C)C	2889.0	Semi standard non polar	33892256
Indicaxanthin,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C	2882.3	Semi standard non polar	33892256
Indicaxanthin,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O[Si](C)(C)C)N1[Si](C)(C)C	2707.4	Standard non polar	33892256
Indicaxanthin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1C/C(=C\C=[N+]2/CCCC2C(=O)[O-])C=C(C(=O)O)N1	3141.4	Semi standard non polar	33892256
Indicaxanthin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O)N1	3134.7	Semi standard non polar	33892256
Indicaxanthin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(C(=O)O)=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC1C(=O)O	3197.7	Semi standard non polar	33892256
Indicaxanthin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O[Si](C)(C)C(C)(C)C)N1	3342.5	Semi standard non polar	33892256
Indicaxanthin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1C/C(=C\C=[N+]2/CCCC2C(=O)[O-])C=C(C(=O)O)N1[Si](C)(C)C(C)(C)C	3402.6	Semi standard non polar	33892256
Indicaxanthin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O)N1[Si](C)(C)C(C)(C)C	3391.6	Semi standard non polar	33892256
Indicaxanthin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	3585.7	Semi standard non polar	33892256
Indicaxanthin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=C/C(=C/C=[N+]2\CCCC2C(=O)[O-])CC(C(=O)O[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	3188.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indicaxanthin GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-7290000000-7ffcbaaf53f96bacbfeb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indicaxanthin GC-MS (2 TMS) - 70eV, Positive	splash10-0006-9216600000-5c7537c320eb3fa5273f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indicaxanthin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - Indicaxanthin 10V, Positive-QTOF	splash10-0a4i-0009000000-9feac245c349b86acfbe	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 20V, Positive-QTOF	splash10-0pb9-2149000000-f009e6e3d83207c817e5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 40V, Positive-QTOF	splash10-014l-9520000000-6fe77bacdc1a667882d2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 10V, Negative-QTOF	splash10-0a4i-0009000000-15475f2f29d9e72bd37a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 20V, Negative-QTOF	splash10-0a4i-3519000000-b7a59996da8ff927fe2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 40V, Negative-QTOF	splash10-0006-9000000000-b27a56182a0b0077d1c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 10V, Positive-QTOF	splash10-0cdi-0094000000-416c7fdd4bed5d0b1793	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 20V, Positive-QTOF	splash10-02ta-0291000000-9f20205d3bdcf262a322	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 40V, Positive-QTOF	splash10-014i-1790000000-5ebc7d7e721609dddc61	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 10V, Negative-QTOF	splash10-03di-0093000000-76ae0d7f1373a94f4074	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 20V, Negative-QTOF	splash10-014r-0961000000-06cf4162e90d887a66c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indicaxanthin 40V, Negative-QTOF	splash10-03du-5930000000-9f3008f89fd7dc45776b	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indicaxanthin

METLIN ID

Not Available

PubChem Compound

12310796

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Indicaxanthin (HMDB0029386)

MOL for HMDB0029386 (Indicaxanthin)

3D MOL for HMDB0029386 (Indicaxanthin)

3D SDF for HMDB0029386 (Indicaxanthin)

3D-SDF for HMDB0029386 (Indicaxanthin)

PDB for HMDB0029386 (Indicaxanthin)

3D PDB for HMDB0029386 (Indicaxanthin)

SMILES for HMDB0029386 (Indicaxanthin)

INCHI for HMDB0029386 (Indicaxanthin)

Structure for HMDB0029386 (Indicaxanthin)

3D Structure for HMDB0029386 (Indicaxanthin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra