NP-MRD: Showing NP-Card for (Indole-3-acetyl)-glucan (NP0050198)

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Record Information

Version

2.0

Created at

2022-04-27 20:33:31 UTC

Updated at

2022-04-27 20:33:31 UTC

NP-MRD ID

NP0050198

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(Indole-3-acetyl)-glucan

Description

(2R,3S,4S,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 2-(1H-indol-3-yl)acetate 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. (Indole-3-acetyl)-glucan is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on (2R,3S,4S,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 2-(1H-indol-3-yl)acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222332D          

 24 26  0  0  1  0            999 V2000
    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
    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
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604   -3.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673   -3.2777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5223   -4.0623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3292   -4.2338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8813   -3.6207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6263   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8194   -2.6646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5644   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1165   -1.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882   -3.7923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842   -5.0184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702   -4.6754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  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 13  1  0  0  0  0
 14 13  1  1  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
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 17 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050198

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@@H]1OC(=O)CC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/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/t11-,13+,14-,15-,16-/m1/s1

> <INCHI_KEY>
XSNPKRVRWPBMKE-DPZJBDQQSA-N

> <FORMULA>
C16H19NO7

> <MOLECULAR_WEIGHT>
337.328

> <EXACT_MASS>
337.116151956

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
32.89454597571708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-0.5583119949999995

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.873268628022618

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.304723874431339

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9817959747176657

> <JCHEM_POLAR_SURFACE_AREA>
132.24

> <JCHEM_REFRACTIVITY>
80.88329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.66e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.250  -4.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.281  -3.189   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.726  -5.798   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.232  -6.118   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.708  -7.583   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.215  -7.903   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.245  -6.759   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.769  -5.294   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.263  -4.974   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.787  -3.509   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.817  -2.365   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.751  -7.079   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.690  -9.368   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.678  -8.727   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    1   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   16                                                            
CONECT   24   15                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S,4S,5R,6R)-4,5,6-Trihydroxy-2-(hydroxymethyl)oxan-3-yl 2-(1H-indol-3-yl)acetic acid	Generator

Chemical Formula

C₁₆H₁₉NO₇

Average Mass

337.3280 Da

Monoisotopic Mass

337.11615 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@@H]1OC(=O)CC1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/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/t11-,13+,14-,15-,16-/m1/s1

InChI Key

XSNPKRVRWPBMKE-DPZJBDQQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	LOTUS Database	35616633

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
Benzenoid
Substituted pyrrole
Oxane
Monosaccharide
Heteroaromatic compound
Pyrrole
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Azacycle
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	0.02	ALOGPS
logP	-0.56	ChemAxon
logS	-1.7	ALOGPS
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	32.89 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

154496032

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)-glucan (NP0050198)

MOL for NP0050198 ((Indole-3-acetyl)-glucan)

3D MOL for NP0050198 ((Indole-3-acetyl)-glucan)

3D SDF for NP0050198 ((Indole-3-acetyl)-glucan)

3D-SDF for NP0050198 ((Indole-3-acetyl)-glucan)

PDB for NP0050198 ((Indole-3-acetyl)-glucan)

3D PDB for NP0050198 ((Indole-3-acetyl)-glucan)

SMILES for NP0050198 ((Indole-3-acetyl)-glucan)

INCHI for NP0050198 ((Indole-3-acetyl)-glucan)

Structure for NP0050198 ((Indole-3-acetyl)-glucan)

3D Structure for NP0050198 ((Indole-3-acetyl)-glucan)