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Showing NP-Card for (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside (NP0336148)

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Record Information
Version2.0
Created at2024-09-11 04:57:12 UTC
Updated at2024-09-11 04:57:12 UTC
NP-MRD IDNP0336148
Secondary Accession NumbersNone
Natural Product Identification
Common Name(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside
Description Based on a literature review very few articles have been published on (R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0336148 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside)


  Mrv2104 05262307292D          

 27 29  0  0  0  0            999 V2000
   -1.8337    0.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998   -0.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164    0.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823    1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    1.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -0.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999    2.7122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    2.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669    1.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4173    1.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0007    1.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8337    2.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164    3.5461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823    2.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    2.4617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -1.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -1.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -2.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -2.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571   -2.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571   -1.8760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218   -2.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007   -2.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -3.5461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9907   -2.8781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9907   -1.5431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  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 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 27  1  0  0  0  0
 19 20  1  0  0  0  0
 19 26  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
Download

3D MOL for NP0336148 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside)

Download
3D SDF for NP0336148 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside)

  Mrv2104 05262307292D          

 27 29  0  0  0  0            999 V2000
   -1.8337    0.2115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9998   -0.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164    0.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823    1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    1.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0007    1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -0.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999    2.7122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    2.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6669    1.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4173    1.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0007    1.0454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8337    2.4617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164    3.5461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5823    2.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    2.4617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -1.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -1.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4117   -2.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -2.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571   -2.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2571   -1.8760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3218   -2.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007   -2.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8339   -3.5461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9907   -2.8781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9907   -1.5431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 15  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 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 27  1  0  0  0  0
 19 20  1  0  0  0  0
 19 26  1  0  0  0  0
 20 21  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC2=CC3=C(NC(=O)C3(O)CC(O)=O)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C16H19NO10/c18-5-9-11(21)12(22)13(23)14(27-9)26-6-1-2-8-7(3-6)16(25,4-10(19)20)15(24)17-8/h1-3,9,11-14,18,21-23,25H,4-5H2,(H,17,24)(H,19,20)

> <INCHI_KEY>
KZKDOIBDOJKQAC-UHFFFAOYNA-N

> <FORMULA>
C16H19NO10

> <MOLECULAR_WEIGHT>
385.325

> <EXACT_MASS>
385.100895816

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.4689290912857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-hydroxy-2-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-indol-3-yl)acetic acid

> <JCHEM_LOGP>
-2.423787712666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.605282242794859

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3717034452390227

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343690392

> <JCHEM_POLAR_SURFACE_AREA>
186.01

> <JCHEM_REFRACTIVITY>
85.7971

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3-hydroxy-2-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H-indol-3-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0336148 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside)
Download
PDB for NP0336148 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -3.423   0.395   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.866  -0.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.777   1.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.087   2.573   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.488   3.039   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.735   1.951   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.557  -1.629   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.933   5.063   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   3.818   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.245   2.883   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.646   3.194   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.735   1.951   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.423   4.595   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.777   6.619   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.087   5.063   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -2.488   4.595   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.557  -2.876   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.635  -3.502   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.635  -4.749   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.557  -5.372   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.480  -4.749   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.480  -3.502   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.601  -5.372   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.681  -4.749   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.557  -6.619   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.716  -5.372   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.716  -2.880   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   16                                                  
CONECT    6    1    5                                                       
CONECT    7    2   17                                                       
CONECT    8    9                                                            
CONECT    9    4    8   10   15                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   15                                                            
CONECT   15    9   14   16                                                  
CONECT   16    5   15                                                       
CONECT   17    7   18   22                                                  
CONECT   18   17   19   27                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   17   21                                                       
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   20                                                            
CONECT   26   19                                                            
CONECT   27   18                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

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3D PDB for NP0336148 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside)
Download
SMILES for NP0336148 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside)
OCC1OC(OC2=CC3=C(NC(=O)C3(O)CC(O)=O)C=C2)C(O)C(O)C1O
Download
INCHI for NP0336148 ((R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 5-glucoside)
InChI=1/C16H19NO10/c18-5-9-11(21)12(22)13(23)14(27-9)26-6-1-2-8-7(3-6)16(25,4-10(19)20)15(24)17-8/h1-3,9,11-14,18,21-23,25H,4-5H2,(H,17,24)(H,19,20)
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View in JSmol
Synonyms
ValueSource
(R)-2,3-Dihydro-3,5-dihydroxy-2-oxo-3-indoleacetate 5-glucosideGenerator
Chemical FormulaC16H19NO10
Average Mass385.3250 Da
Monoisotopic Mass385.10090 Da
IUPAC Name2-(3-hydroxy-2-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-indol-3-yl)acetic acid
Traditional Name(3-hydroxy-2-oxo-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H-indol-3-yl)acetic acid
CAS Registry NumberNot Available
SMILES
OCC1OC(OC2=CC3=C(NC(=O)C3(O)CC(O)=O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=1/C16H19NO10/c18-5-9-11(21)12(22)13(23)14(27-9)26-6-1-2-8-7(3-6)16(25,4-10(19)20)15(24)17-8/h1-3,9,11-14,18,21-23,25H,4-5H2,(H,17,24)(H,19,20)
InChI KeyKZKDOIBDOJKQAC-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ChemAxon
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.01 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.8 m³·mol⁻¹ChemAxon
Polarizability35.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available