NP-MRD: Showing NP-Card for Indican glucoside (NP0050715)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:03:15 UTC

Updated at

2022-04-27 22:03:15 UTC

NP-MRD ID

NP0050715

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Indican glucoside

Description

Indican, also known as indican, plant or uroxanthin, 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. Indican is an extremely weak basic (essentially neutral) compound (based on its pKa). Indican is a colourless organic compound, soluble in water, naturally occurring in Indigofera plants. Indican interferes with many commercial procedures for measuring total bilirubin which can be a problem for renal failure patients where blood indican levels are raised. Tryptophan is first converted to indole (excreted in faeces), then to indican by bacteria in the gut. The enzyme "indoxyl esterase" has been found in humans and is involved in another pathway of chemical reactions involving indoxyl. A reaction, similar to the above-mentioned is seen in the normal population, who excrete small amounts of the chemical in their urine. Indican glucoside is found in Calanthe discolor, Celosia argentea, Indigofera spp. , Indigofera suffruticosa, Indigofera tinctoria , Isatis indigotica , Polygonum perfoliatum, Polygonum tinctorium, Polygonum tinctorum and Strobilanthes cusia. Indican glucoside was first documented in 1975 (PMID: 1199990). Common and significant reactions involving indican are as follows:Indican is a glycoside.

Structure

MOL SDF PDB SMILES InChI

      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>
NP0050715

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

295.2910 Da

Monoisotopic Mass

295.10559 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Calanthe discolor	LOTUS Database	35616633
Celosia argentea	LOTUS Database	35616633
Indigofera spp.	Plant	KNApSAcK
Indigofera suffruticosa	LOTUS Database	35616633
Indigofera tinctoria	Plant	KNApSAcK
Isatis tinctoria	Plant	KNApSAcK
Polygonum perfoliatum	Plant	KNApSAcK
Polygonum tinctorium	Plant	KNApSAcK
Polygonum tinctorum	Plant	KNApSAcK
Strobilanthes cusia	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0061755

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

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. doi: 10.1007/BF01071187. [PubMed:1199990 ]

Showing NP-Card for Indican glucoside (NP0050715)

MOL for NP0050715 (Indican glucoside)

3D MOL for NP0050715 (Indican glucoside)

3D SDF for NP0050715 (Indican glucoside)

3D-SDF for NP0050715 (Indican glucoside)

PDB for NP0050715 (Indican glucoside)

3D PDB for NP0050715 (Indican glucoside)

SMILES for NP0050715 (Indican glucoside)

INCHI for NP0050715 (Indican glucoside)

Structure for NP0050715 (Indican glucoside)

3D Structure for NP0050715 (Indican glucoside)