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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2014-09-22 19:36:58 UTC

Update Date

2021-09-14 15:44:45 UTC

HMDB ID

HMDB0061755

Secondary Accession Numbers

HMDB61755

Metabolite Identification

Common Name

Indican

Description

Indican is a colourless, water-soluble organic compound consisting of an indole ring conjugated to glucose. It is an indole glycoside. Its hydrolysis yields β-D-glucose and indoxyl. Indoles are compounds which consist of a pyrrole ring fused to benzene to form 2,3-benzopyrrole. The oxidation of indican by a mild oxidizing agent, e.g. atmospheric oxygen or CYP450 enzymes, yields indigo dye which is blue in colour. Indican is a substance occurring naturally in the urine of humans and mammals and also in blood plasma as a normal metabolite of tryptophan. Tryptophan is first converted to indole by gut bacteria. Following absorption from the gut, indole is converted to 3-hydroxyindole (indoxyl or indican) in the liver, where it is again then conjugated with sulfuric acid or glucoronic acid through normal xenobiotic metabolism pathways. It is then transported to the kidneys for excretion. In individuals affected by the blue diaper syndrome (a rare, autosomal recessive metabolic disorder characterized in infants by bluish urine-stained diapers), the patients exhibit a defect in tryptophan metabolism, leading to an increase in indican synthesis. Indican is then excreted into the urine and from there into the diaper where, upon exposure to air, it is converted to indigo blue dye due to oxidation by atmospheric oxygen. An increased urinary excretion of indican is seen in Hartnup disease from the bacterial degradation of unabsorbed tryptophan (PMID: 19967017 ). Hartnup disease is an autosomal recessive metabolic disorder affecting the absorption of nonpolar amino acids (particularly tryptophan), which leads to excessive bacterial fermentation of tryptophan (to indole) in the gut. Indican has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). Its excretion is decreased by the presence of Lactobacillus bacteria in the gut (PMID: 6785555 ).

Structure

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

HMDB0061755
     RDKit          3D
Indican
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.8978    2.7705    0.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530    2.1745   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.9090   -0.2756 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5752    0.3162   -1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496   -0.4350   -0.3930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.8563   -1.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457   -0.7572   -1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -1.4193   -2.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8451   -1.1165   -1.7976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430   -0.2939   -0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0367    0.2850   -0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8514    1.1099    0.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    1.3450    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    0.7734    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671   -0.0570   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377   -1.6086    0.2230 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5408   -2.2210    1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343   -1.1442    0.9778 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4398   -2.2079    1.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -0.1193    0.1509 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4722    0.3891    0.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    3.7165   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    2.9099   -1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851    1.9208   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.2012    0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766    0.2446    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1746   -2.0548   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039   -1.4498   -2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0389    0.0974   -0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7093    1.5742    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    1.9982    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4789    0.9739    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -2.3326   -0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0645   -2.7806    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -0.6411    1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9079   -3.0070    1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6835   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313    0.4762    1.8449 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
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 15  7  1  0
 15 10  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  1
  5 26  1  1
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  6
 17 34  1  0
 18 35  1  1
 19 36  1  0
 20 37  1  6
 21 38  1  0
M  END

      ChEBI
  Mrv1652306021801022D          

 21 23  0  0  1  0            999 V2000
   14.7243   -6.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4387   -6.6551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7243   -7.8927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7243   -8.7177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0098   -6.6551    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.2953   -6.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4387   -7.4801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1530   -7.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0098   -7.4801    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2953   -7.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1530   -6.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8677   -6.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6726   -6.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0936   -7.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7911   -7.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5487   -7.8034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0766   -5.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9017   -5.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9185   -7.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3226   -6.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5808   -6.6551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  2  1  0  0  0  0
  5  9  1  0  0  0  0
  9  3  1  0  0  0  0
  3  7  1  0  0  0  0
  7  2  1  0  0  0  0
  2 11  1  1  0  0  0
  3  4  1  1  0  0  0
  5  6  1  1  0  0  0
  7  8  1  6  0  0  0
  9 10  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  0  0  0  0
 15 12  2  0  0  0  0
 17 13  1  0  0  0  0
 14 13  2  0  0  0  0
 16 14  1  0  0  0  0
 19 14  1  0  0  0  0
 16 15  1  0  0  0  0
 18 17  2  0  0  0  0
 20 18  1  0  0  0  0
 20 19  2  0  0  0  0
  6 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061755

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@@H](OC2=CNC3=C2C=CC=C3)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1

> <INCHI_KEY>
XVARCVCWNFACQC-RKQHYHRCSA-N

> <FORMULA>
C14H17NO6

> <MOLECULAR_WEIGHT>
295.291

> <EXACT_MASS>
295.105587271

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.69420178511018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-0.49962560599999967

> <ALOGPS_LOGS>
-1.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.194893469520824

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199910755914217

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092351788609

> <JCHEM_POLAR_SURFACE_AREA>
115.17000000000002

> <JCHEM_REFRACTIVITY>
71.2698

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061755
     RDKit          3D
Indican
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.8978    2.7705    0.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530    2.1745   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.9090   -0.2756 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5752    0.3162   -1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496   -0.4350   -0.3930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.8563   -1.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457   -0.7572   -1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -1.4193   -2.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8451   -1.1165   -1.7976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430   -0.2939   -0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0367    0.2850   -0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8514    1.1099    0.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    1.3450    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    0.7734    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671   -0.0570   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377   -1.6086    0.2230 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5408   -2.2210    1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343   -1.1442    0.9778 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4398   -2.2079    1.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -0.1193    0.1509 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4722    0.3891    0.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    3.7165   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    2.9099   -1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851    1.9208   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.2012    0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766    0.2446    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1746   -2.0548   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039   -1.4498   -2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0389    0.0974   -0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7093    1.5742    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    1.9982    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4789    0.9739    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -2.3326   -0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0645   -2.7806    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -0.6411    1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9079   -3.0070    1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6835   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313    0.4762    1.8449 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
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 15  7  1  0
 15 10  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  1
  5 26  1  1
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  6
 17 34  1  0
 18 35  1  1
 19 36  1  0
 20 37  1  6
 21 38  1  0
M  END

HEADER    PROTEIN                                 02-JUN-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:       ChEBI                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-JUN-18         0                                  
HETATM    1  O   UNK     0      27.485 -11.653   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      28.819 -12.423   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.485 -14.733   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.485 -16.273   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      26.152 -12.423   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.818 -11.653   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.819 -13.963   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      30.152 -14.733   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      26.152 -13.963   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      24.818 -14.733   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      30.152 -11.653   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      31.486 -12.423   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.989 -12.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.775 -13.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.343 -13.957   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      32.758 -14.566   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      33.743 -10.742   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.283 -10.724   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.315 -13.391   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.069 -12.048   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      23.484 -12.423   0.000  0.00  0.00           O+0
CONECT    1    5    2                                                       
CONECT    2    1    7   11                                                  
CONECT    3    9    7    4                                                  
CONECT    4    3                                                            
CONECT    5    1    9    6                                                  
CONECT    6    5   21                                                       
CONECT    7    3    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5    3   10                                                  
CONECT   10    9                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   17   14                                                  
CONECT   14   13   16   19                                                  
CONECT   15   12   16                                                       
CONECT   16   14   15                                                       
CONECT   17   13   18                                                       
CONECT   18   17   20                                                       
CONECT   19   14   20                                                       
CONECT   20   18   19                                                       
CONECT   21    6                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0061755
HETATM    1  O1  UNL     1       3.898   2.771   0.111  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.053   2.174  -0.793  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.426   0.909  -0.276  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.575   0.316  -1.198  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.650  -0.435  -0.393  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.410  -0.856  -1.058  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.746  -0.757  -1.089  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.577  -1.419  -2.036  1.00  0.00           C  
HETATM    9  N1  UNL     1      -3.845  -1.116  -1.798  1.00  0.00           N  
HETATM   10  C6  UNL     1      -3.943  -0.294  -0.755  1.00  0.00           C  
HETATM   11  C7  UNL     1      -5.037   0.285  -0.142  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.851   1.110   0.937  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.584   1.345   1.388  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.463   0.773   0.788  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.667  -0.057  -0.300  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.438  -1.609   0.223  1.00  0.00           C  
HETATM   17  O4  UNL     1       0.541  -2.221   1.113  1.00  0.00           O  
HETATM   18  C13 UNL     1       2.634  -1.144   0.978  1.00  0.00           C  
HETATM   19  O5  UNL     1       3.440  -2.208   1.321  1.00  0.00           O  
HETATM   20  C14 UNL     1       3.425  -0.119   0.151  1.00  0.00           C  
HETATM   21  O6  UNL     1       4.472   0.389   0.897  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.023   3.716  -0.173  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.265   2.910  -1.053  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.585   1.921  -1.734  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.847   1.201   0.649  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.477   0.245   0.458  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.175  -2.055  -2.803  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.704  -1.450  -2.326  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.039   0.097  -0.501  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.709   1.574   1.431  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.407   1.998   2.247  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.479   0.974   1.161  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.713  -2.333  -0.545  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.065  -2.781   0.555  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.305  -0.641   1.912  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.908  -3.007   1.541  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.794  -0.683  -0.733  1.00  0.00           H  
HETATM   38  H17 UNL     1       4.231   0.476   1.845  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3   23   24
CONECT    3    4   20   25
CONECT    4    5
CONECT    5    6   16   26
CONECT    6    7
CONECT    7    8    8   15
CONECT    8    9   27
CONECT    9   10   28
CONECT   10   11   11   15
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   16   17   18   33
CONECT   17   34
CONECT   18   19   20   35
CONECT   19   36
CONECT   20   21   37
CONECT   21   38
END

HMDB0061755
     RDKit          3D
Indican
 38 40  0  0  0  0  0  0  0  0999 V2000
    3.8978    2.7705    0.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0530    2.1745   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.9090   -0.2756 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5752    0.3162   -1.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6496   -0.4350   -0.3930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.8563   -1.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457   -0.7572   -1.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5768   -1.4193   -2.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8451   -1.1165   -1.7976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9430   -0.2939   -0.7547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0367    0.2850   -0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8514    1.1099    0.9374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5840    1.3450    1.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    0.7734    0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671   -0.0570   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377   -1.6086    0.2230 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5408   -2.2210    1.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6343   -1.1442    0.9778 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4398   -2.2079    1.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251   -0.1193    0.1509 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4722    0.3891    0.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    3.7165   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    2.9099   -1.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851    1.9208   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.2012    0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4766    0.2446    0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1746   -2.0548   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7039   -1.4498   -2.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0389    0.0974   -0.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7093    1.5742    1.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4072    1.9982    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4789    0.9739    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133   -2.3326   -0.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0645   -2.7806    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -0.6411    1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9079   -3.0070    1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6835   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2313    0.4762    1.8449 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
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  5 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  3  1  0
 15  7  1  0
 15 10  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  1
  5 26  1  1
  8 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  6
 17 34  1  0
 18 35  1  1
 19 36  1  0
 20 37  1  6
 21 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Indican, plant	ChEBI
1H-indol-3-yl beta-Glucopyranoside	HMDB
1H-indol-3-yl Β-D-glucopyranoside	HMDB
Indoxyl-β-D-glucoside	HMDB
1H-indol-3-yl beta-D-Glucopyranoside	HMDB
Indoxyl-beta-D-glucoside	HMDB
3-(Glucosyloxy)indole	HMDB
Uroxanthin	HMDB

Chemical Formula

C₁₄H₁₇NO₆

Average Molecular Weight

295.291

Monoisotopic Molecular Weight

295.105587271

IUPAC Name

(2R,3S,4S,5R)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol

CAS Registry Number

487-60-5

SMILES

OC[C@H]1O[C@@H](OC2=CNC3=C2C=CC=C3)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1

InChI Key

XVARCVCWNFACQC-RKQHYHRCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Indole
Indole or derivatives
Monosaccharide
Oxane
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Secondary alcohol
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:16700 )
indolyl carbohydrate (CHEBI:16700 )
exopolysaccharide (CHEBI:16700 )

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	-0.33	ALOGPS
logP	-0.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	115.17 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.27 m³·mol⁻¹	ChemAxon
Polarizability	28.69 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	166.302	31661259
DarkChem	[M-H]-	165.079	31661259
DeepCCS	[M+H]+	166.077	30932474
DeepCCS	[M-H]-	163.681	30932474
DeepCCS	[M-2H]-	197.884	30932474
DeepCCS	[M+Na]+	172.885	30932474
AllCCS	[M+H]+	170.1	32859911
AllCCS	[M+H-H2O]+	166.7	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.2	32859911
AllCCS	[M-H]-	167.1	32859911
AllCCS	[M+Na-2H]-	166.8	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indican	OC[C@H]1O[C@@H](OC2=CNC3=C2C=CC=C3)[C@H](O)[C@@H](O)[C@@H]1O	3905.3	Standard polar	33892256
Indican	OC[C@H]1O[C@@H](OC2=CNC3=C2C=CC=C3)[C@H](O)[C@@H](O)[C@@H]1O	2898.4	Standard non polar	33892256
Indican	OC[C@H]1O[C@@H](OC2=CNC3=C2C=CC=C3)[C@H](O)[C@@H](O)[C@@H]1O	3001.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indican,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	2735.4	Semi standard non polar	33892256
Indican,1TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@H](CO)[C@@H](O)[C@@H]1O	2717.8	Semi standard non polar	33892256
Indican,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@H](CO)[C@H]1O	2708.1	Semi standard non polar	33892256
Indican,1TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O	2710.8	Semi standard non polar	33892256
Indican,1TMS,isomer #5	C[Si](C)(C)N1C=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C21	2752.4	Semi standard non polar	33892256
Indican,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	2701.2	Semi standard non polar	33892256
Indican,2TMS,isomer #10	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O	2733.2	Semi standard non polar	33892256
Indican,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	2705.6	Semi standard non polar	33892256
Indican,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	2693.8	Semi standard non polar	33892256
Indican,2TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	2715.2	Semi standard non polar	33892256
Indican,2TMS,isomer #5	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@@H]1CO	2729.9	Semi standard non polar	33892256
Indican,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@H](CO)[C@H]1O	2737.1	Semi standard non polar	33892256
Indican,2TMS,isomer #7	C[Si](C)(C)O[C@H]1[C@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)O[C@H](CO)[C@@H](O)[C@@H]1O	2730.9	Semi standard non polar	33892256
Indican,2TMS,isomer #8	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C	2721.5	Semi standard non polar	33892256
Indican,2TMS,isomer #9	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)O[C@H](CO)[C@H]1O	2727.2	Semi standard non polar	33892256
Indican,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2767.3	Semi standard non polar	33892256
Indican,3TMS,isomer #10	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C	2758.5	Semi standard non polar	33892256
Indican,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2770.4	Semi standard non polar	33892256
Indican,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	2734.4	Semi standard non polar	33892256
Indican,3TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2759.0	Semi standard non polar	33892256
Indican,3TMS,isomer #5	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	2742.8	Semi standard non polar	33892256
Indican,3TMS,isomer #6	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	2735.5	Semi standard non polar	33892256
Indican,3TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@H](CO)[C@H]1O[Si](C)(C)C	2800.6	Semi standard non polar	33892256
Indican,3TMS,isomer #8	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)O[C@@H]1CO	2760.9	Semi standard non polar	33892256
Indican,3TMS,isomer #9	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)O[C@H](CO)[C@H]1O	2771.7	Semi standard non polar	33892256
Indican,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2848.0	Semi standard non polar	33892256
Indican,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2808.3	Semi standard non polar	33892256
Indican,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2813.9	Semi standard non polar	33892256
Indican,4TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2803.0	Semi standard non polar	33892256
Indican,4TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)O[C@H](CO)[C@H]1O[Si](C)(C)C	2834.9	Semi standard non polar	33892256
Indican,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2887.6	Semi standard non polar	33892256
Indican,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2813.9	Standard non polar	33892256
Indican,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2922.3	Standard polar	33892256
Indican,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3008.8	Semi standard non polar	33892256
Indican,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@H](CO)[C@@H](O)[C@@H]1O	3009.0	Semi standard non polar	33892256
Indican,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@H](CO)[C@H]1O	2990.7	Semi standard non polar	33892256
Indican,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O	2990.8	Semi standard non polar	33892256
Indican,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N1C=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C21	3007.4	Semi standard non polar	33892256
Indican,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3268.7	Semi standard non polar	33892256
Indican,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O	3212.1	Semi standard non polar	33892256
Indican,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3263.7	Semi standard non polar	33892256
Indican,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3258.3	Semi standard non polar	33892256
Indican,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3198.9	Semi standard non polar	33892256
Indican,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@@H]1CO	3264.5	Semi standard non polar	33892256
Indican,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@H](CO)[C@H]1O	3263.3	Semi standard non polar	33892256
Indican,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)O[C@H](CO)[C@@H](O)[C@@H]1O	3225.8	Semi standard non polar	33892256
Indican,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3248.3	Semi standard non polar	33892256
Indican,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)O[C@H](CO)[C@H]1O	3207.4	Semi standard non polar	33892256
Indican,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3485.7	Semi standard non polar	33892256
Indican,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3414.6	Semi standard non polar	33892256
Indican,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3512.0	Semi standard non polar	33892256
Indican,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3408.1	Semi standard non polar	33892256
Indican,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3489.0	Semi standard non polar	33892256
Indican,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3405.5	Semi standard non polar	33892256
Indican,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3403.9	Semi standard non polar	33892256
Indican,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=C[NH]C3=CC=CC=C23)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C	3496.4	Semi standard non polar	33892256
Indican,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)O[C@@H]1CO	3426.9	Semi standard non polar	33892256
Indican,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)O[C@H](CO)[C@H]1O	3429.4	Semi standard non polar	33892256
Indican,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3725.0	Semi standard non polar	33892256
Indican,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3574.2	Semi standard non polar	33892256
Indican,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3616.6	Semi standard non polar	33892256
Indican,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3579.3	Semi standard non polar	33892256
Indican,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C	3594.5	Semi standard non polar	33892256
Indican,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3789.6	Semi standard non polar	33892256
Indican,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3656.0	Standard non polar	33892256
Indican,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3368.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indican GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indican 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 - Indican 10V, Positive-QTOF	splash10-001j-0970000000-7aced476e9b336ccabe1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 20V, Positive-QTOF	splash10-001i-0900000000-a7c5e604d3a530d54d50	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 40V, Positive-QTOF	splash10-001i-2900000000-2b1f1110128789c271b7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 10V, Negative-QTOF	splash10-000x-0790000000-1818b20ca7f0bf93e1b0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 20V, Negative-QTOF	splash10-001i-0910000000-ad78f9fbe343f0a32dce	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 40V, Negative-QTOF	splash10-0f89-2900000000-b7c9419dfcdc464baae3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 10V, Negative-QTOF	splash10-000x-0950000000-394b329d78ea1225cebb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 20V, Negative-QTOF	splash10-001i-2910000000-e0db1f842a7808101d62	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 40V, Negative-QTOF	splash10-001i-5900000000-31d334dd93190a572458	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 10V, Positive-QTOF	splash10-001j-0950000000-3a223b0b909951116c0e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 20V, Positive-QTOF	splash10-001i-0980000000-3911da154bca34692f99	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indican 40V, Positive-QTOF	splash10-014i-6910000000-d730ad1f7964f451245f	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	39.79 +/- 1.59 uM	Adult (>18 years old)	Both	Normal	22626821	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	92.51 +/- 45.07 uM	Adult (>18 years old)	Both	uremia	22626821	details

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

Not Available

KNApSAcK ID

C00001541

Chemspider ID

390239

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Indican

METLIN ID

Not Available

PubChem Compound

441564

PDB ID

Not Available

ChEBI ID

16700

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

Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Mayer PJ, Beeken WL: The role of urinary indican as a predictor of bacterial colonization in the human jejunum. Am J Dig Dis. 1975 Nov;20(11):1003-9. [PubMed:1199990 ]
Tohyama K, Kobayashi Y, Kan T, Yazawa K, Terashima T, Mutai M: Effect of lactobacilli on urinary indican excretion in gnotobiotic rats and in man. Microbiol Immunol. 1981;25(2):101-12. [PubMed:6785555 ]
Patel AB, Prabhu AS: Hartnup disease. Indian J Dermatol. 2008 Jan;53(1):31-2. doi: 10.4103/0019-5154.39740. [PubMed:19967017 ]

Showing metabocard for Indican (HMDB0061755)

MOL for HMDB0061755 (Indican)

3D MOL for HMDB0061755 (Indican)

3D SDF for HMDB0061755 (Indican)

3D-SDF for HMDB0061755 (Indican)

PDB for HMDB0061755 (Indican)

3D PDB for HMDB0061755 (Indican)

SMILES for HMDB0061755 (Indican)

INCHI for HMDB0061755 (Indican)

Structure for HMDB0061755 (Indican)

3D Structure for HMDB0061755 (Indican)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra