NP-MRD: Showing NP-Card for indole-3-acetyl-β-4-D-glucose (NP0339914)

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Record Information

Version

2.0

Created at

2024-09-12 00:11:26 UTC

Updated at

2024-09-12 00:11:26 UTC

NP-MRD ID

NP0339914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

indole-3-acetyl-β-4-D-glucose

Description

Indole-3-acetyl-β-4-D-glucose 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. Based on a literature review very few articles have been published on indole-3-acetyl-β-4-D-glucose.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272302432D          

 24 26  0  0  0  0            999 V2000
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8194    1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263    1.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1784    0.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8813    2.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882    2.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    2.8379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702    3.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633    3.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 17  1  0  0  0  0
  7 20  2  0  0  0  0
  1  5  2  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339914

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(O)C(O)C(O)C1OC(=O)CC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1/C16H19NO7/c18-7-11-15(13(20)14(21)16(22)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

> <INCHI_KEY>
XSNPKRVRWPBMKE-UHFFFAOYNA-N

> <FORMULA>
C16H19NO7

> <MOLECULAR_WEIGHT>
337.328

> <EXACT_MASS>
337.116151956

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.324220203035885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-0.5583119949999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.873268628022617

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.304723874431339

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9817959747176657

> <JCHEM_POLAR_SURFACE_AREA>
132.24

> <JCHEM_REFRACTIVITY>
80.8833

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.726   3.192   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.232   3.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.263   2.368   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.787   0.904   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.769   2.688   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.800   1.544   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -7.245   4.153   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -8.751   4.473   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.215   5.297   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.708   4.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.678   6.122   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.171   5.802   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.281   0.583   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6    1                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18    9                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    7                                                            
CONECT   21    4   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₉NO₇

Average Mass

337.3280 Da

Monoisotopic Mass

337.11615 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OCC1OC(O)C(O)C(O)C1OC(=O)CC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1/C16H19NO7/c18-7-11-15(13(20)14(21)16(22)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

InChI Key

XSNPKRVRWPBMKE-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as indole-3-acetic acid derivatives. These 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
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (INDOLE-3-ACETYL-BETA-4-D-GLUCOSE )

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	-0.56	ChemAxon
pKa (Strongest Acidic)	11.3	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	32.32 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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for indole-3-acetyl-β-4-D-glucose (NP0339914)

MOL for NP0339914 (indole-3-acetyl-β-4-D-glucose)

3D MOL for NP0339914 (indole-3-acetyl-β-4-D-glucose)

3D SDF for NP0339914 (indole-3-acetyl-β-4-D-glucose)

3D-SDF for NP0339914 (indole-3-acetyl-β-4-D-glucose)

PDB for NP0339914 (indole-3-acetyl-β-4-D-glucose)

3D PDB for NP0339914 (indole-3-acetyl-β-4-D-glucose)

SMILES for NP0339914 (indole-3-acetyl-β-4-D-glucose)

INCHI for NP0339914 (indole-3-acetyl-β-4-D-glucose)

Structure for NP0339914 (indole-3-acetyl-β-4-D-glucose)

3D Structure for NP0339914 (indole-3-acetyl-β-4-D-glucose)