NP-MRD: Showing NP-Card for Indole-3-carboxylic acid beta-D-glucopyranosyl ester (NP0055023)

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Record Information

Version

2.0

Created at

2022-04-28 01:11:33 UTC

Updated at

2022-04-28 01:11:34 UTC

NP-MRD ID

NP0055023

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Indole-3-carboxylic acid beta-D-glucopyranosyl ester

Description

SCHEMBL326630 belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole. Indole-3-carboxylic acid beta-D-glucopyranosyl ester is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on SCHEMBL326630.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    1.0369   -0.1767   -1.8318 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9519   -0.1002   -0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3319   -0.0085   -0.0554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -0.0001   -0.8745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0797    1.2328   -0.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0457    1.3443    0.2075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4881    1.3334    1.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087    2.3722    1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642    0.3533    0.0852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3437    0.9513   -0.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -0.7806   -0.8575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6807   -1.8624   -0.6269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911   -1.1592   -0.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0412   -2.2064   -1.4590 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360   -0.1075    0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097   -0.0314    1.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4843   -0.0677    2.0677 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2543   -0.1696    0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6191   -0.2437    0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1479   -0.3425   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3558   -0.3700   -1.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -0.2947   -1.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -0.1949   -0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290   -0.0792   -1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5122    2.3645    0.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9851    0.3522    1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2972    1.4153    2.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8807    2.1317    2.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4066   -0.0400    1.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3148    1.9387   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9207   -0.4209   -1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9660   -2.2014   -1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2783   -1.5700    0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1807   -1.9995   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202    0.0476    2.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518   -0.0279    3.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2391   -0.2219    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2465   -0.4002   -0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7955   -0.4481   -2.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3107   -0.3119   -2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  4 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  0
  9  6  1  0
 23 15  1  0
 23 18  1  0
  8 28  1  0
  7 26  1  0
  7 27  1  0
  6 25  1  6
  4 24  1  6
 16 35  1  0
 17 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 13 33  1  1
 14 34  1  0
 11 31  1  6
 12 32  1  0
  9 29  1  1
 10 30  1  0
M  END


  Mrv1652304282203112D          

 23 25  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    3.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    4.3727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3739    4.5442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1190    5.3289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6710    5.9420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4780    5.7704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7329    4.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300    6.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751    7.1682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    6.7266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880    5.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    3.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  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
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  1  0  0  0
 19 20  1  0  0  0  0
 16 21  1  6  0  0  0
 15 22  1  1  0  0  0
 14 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0055023

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC(=O)C2=CNC3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H17NO7/c17-6-10-11(18)12(19)13(20)15(22-10)23-14(21)8-5-16-9-4-2-1-3-7(8)9/h1-5,10-13,15-20H,6H2/t10-,11-,12+,13-,15+/m1/s1

> <INCHI_KEY>
OQZPHKHJQADXAS-VVSAWPALSA-N

> <FORMULA>
C15H17NO7

> <MOLECULAR_WEIGHT>
323.301

> <EXACT_MASS>
323.100501891

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.80858183376991

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.26

> <JCHEM_LOGP>
-0.3384773763333331

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.421545648767733

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.849579767817817

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938238994806

> <JCHEM_POLAR_SURFACE_AREA>
132.24

> <JCHEM_REFRACTIVITY>
76.8319

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 1H-indole-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.143   5.874   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.680   6.698   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.204   8.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.698   8.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.222   9.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.253  11.092   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.759  10.771   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.235   9.307   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.789  11.916   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.313  13.381   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.777  12.556   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.284  10.267   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.333   7.338   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   16                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₇NO₇

Average Mass

323.3010 Da

Monoisotopic Mass

323.10050 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC(=O)C2=CNC3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C15H17NO7/c17-6-10-11(18)12(19)13(20)15(22-10)23-14(21)8-5-16-9-4-2-1-3-7(8)9/h1-5,10-13,15-20H,6H2/t10-,11-,12+,13-,15+/m1/s1

InChI Key

OQZPHKHJQADXAS-VVSAWPALSA-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
Arabidopsis thaliana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-0.26	ALOGPS
logP	-0.34	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	11.85	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	4	ChemAxon
Refractivity	76.83 m³·mol⁻¹	ChemAxon
Polarizability	31.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

95502771

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45783237

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

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References

General References

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Showing NP-Card for Indole-3-carboxylic acid beta-D-glucopyranosyl ester (NP0055023)

MOL for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

3D MOL for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

3D SDF for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

3D-SDF for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

PDB for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

3D PDB for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

SMILES for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

INCHI for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

Structure for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)

3D Structure for NP0055023 (Indole-3-carboxylic acid beta-D-glucopyranosyl ester)