NP-MRD: Showing NP-Card for 4-O-(Indole-3-acetyl)-D-glucopyranose (NP0045533)

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Record Information

Version

2.0

Created at

2022-03-17 19:25:20 UTC

Updated at

2022-03-17 19:25:20 UTC

NP-MRD ID

NP0045533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-O-(Indole-3-acetyl)-D-glucopyranose

Description

4-O-(Indole-3-acetyl)-D-glucopyranose is found in Apis cerana and Arabidopsis thaliana.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212162D          

 24 26  0  0  0  0            999 V2000
   -0.0589   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -2.2687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857   -0.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825   -0.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7961   -1.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514    1.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514    1.9845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1659    2.3970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8804    1.9845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8804    1.1595    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1659    0.7470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1659   -0.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5948    0.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7370    2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1659    3.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5949    2.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7370    3.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  9  2  1  0  0  0  0
  2  3  1  0  0  0  0
  7  3  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  1  0  0  0  0
 11 12  2  0  0  0  0
 11 19  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 17 20  1  6  0  0  0
 14 21  1  1  0  0  0
 15 22  1  6  0  0  0
 16 23  1  1  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045533

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC(=O)CC2=CNC3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO7/c18-7-11-13(20)14(21)15(22)16(23-11)24-12(19)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-18,20-22H,5,7H2/t11-,13-,14+,15-,16+/m1/s1

> <INCHI_KEY>
HHDMMUWDSFASNB-JZYAIQKZSA-N

> <FORMULA>
C16H19NO7

> <MOLECULAR_WEIGHT>
337.3246

> <EXACT_MASS>
337.116151967

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.709777696358522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-(1H-indol-3-yl)acetate

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-0.5583119949999996

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.189115728526989

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195536206159124

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810936792926377

> <JCHEM_POLAR_SURFACE_AREA>
132.24

> <JCHEM_REFRACTIVITY>
80.88329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iaa-glucose

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.110  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.444  -1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.444  -3.465   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.110  -4.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.224  -3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.224  -1.925   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.777  -4.235   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.111  -3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.111  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.200  -0.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.687  -1.235   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.086  -2.722   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -6.443   2.164   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.443   3.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.776   4.474   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.110   3.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.110   2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.776   1.394   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.776  -0.146   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -10.444   1.394   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.109   4.474   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.776   6.014   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0     -10.444   4.474   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.109   6.014   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    9    3                                                  
CONECT    3    4    2    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    2    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11                                                            
CONECT   13   14   18                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   20                                                  
CONECT   18   13   17   19                                                  
CONECT   19   11   18                                                       
CONECT   20   17                                                            
CONECT   21   14   24                                                       
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
1-O-(indol-3-yl)Acetyl-beta-D-glucose	ChEBI
1-O-(Indole-3-acetyl)-beta-1-D-glucose	ChEBI
1-O-indol-3-Ylacetyl-beta-D-glucose	ChEBI
1-O-indol-3-Ylacetylglucose	ChEBI
beta-D-Glucopyranose, 1-(1H-indole-3-acetate)	ChEBI
Iaa-glucose	ChEBI
Indole-3-acetic acid beta-D-glucoside	ChEBI
Indole-3-acetyl-beta-1-D-glucose	ChEBI
Indole-3-acetyl-beta-1-D-glucoside	ChEBI
1-O-(indol-3-yl)Acetyl-b-D-glucose	Generator
1-O-(indol-3-yl)Acetyl-β-D-glucose	Generator
1-O-(Indole-3-acetyl)-b-1-D-glucose	Generator
1-O-(Indole-3-acetyl)-β-1-D-glucose	Generator
1-O-indol-3-Ylacetyl-b-D-glucose	Generator
1-O-indol-3-Ylacetyl-β-D-glucose	Generator
b-D-Glucopyranose, 1-(1H-indole-3-acetate)	Generator
b-D-Glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
beta-D-Glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
Β-D-glucopyranose, 1-(1H-indole-3-acetate)	Generator
Β-D-glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
Indole-3-acetate b-D-glucoside	Generator
Indole-3-acetate beta-D-glucoside	Generator
Indole-3-acetate β-D-glucoside	Generator
Indole-3-acetic acid b-D-glucoside	Generator
Indole-3-acetic acid β-D-glucoside	Generator
Indole-3-acetyl-b-1-D-glucose	Generator
Indole-3-acetyl-β-1-D-glucose	Generator
Indole-3-acetyl-b-1-D-glucoside	Generator
Indole-3-acetyl-β-1-D-glucoside	Generator

Chemical Formula

C₁₆H₁₉NO₇

Average Mass

337.3246 Da

Monoisotopic Mass

337.11615 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 2-(1H-indol-3-yl)acetate

Traditional Name

iaa-glucose

CAS Registry Number

52703-89-6

SMILES

OC[C@H]1O[C@@H](OC(=O)CC2=CNC3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C16H19NO7/c18-7-11-13(20)14(21)15(22)16(23-11)24-12(19)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-18,20-22H,5,7H2/t11-,13-,14+,15-,16+/m1/s1

InChI Key

HHDMMUWDSFASNB-JZYAIQKZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Arabidopsis thaliana	Plant	KNApSAcK
Zea mays L.	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
Hexose monosaccharide
3-alkylindole
Indole
Monosaccharide
Oxane
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Primary alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolyl carbohydrate (CHEBI:17990 )
indoleacetic acid ester conjugate (CHEBI:17990 )

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	0.02	ALOGPS
logP	-0.56	ChemAxon
logS	-1.7	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	132.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.88 m³·mol⁻¹	ChemAxon
Polarizability	31.71 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001408

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04197

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440255

PDB ID

Not Available

ChEBI ID

17990

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-O-(Indole-3-acetyl)-D-glucopyranose (NP0045533)

MOL for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D MOL for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D SDF for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D-SDF for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

PDB for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D PDB for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

SMILES for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

INCHI for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

Structure for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D Structure for NP0045533 (4-O-(Indole-3-acetyl)-D-glucopyranose)