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Showing NP-Card for (2,7-dihydroxy-3h-indol-3-yl)acetic acid (NP0296402)

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Record Information
Version2.0
Created at2022-09-10 05:57:44 UTC
Updated at2022-09-10 05:57:44 UTC
NP-MRD IDNP0296402
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2,7-dihydroxy-3h-indol-3-yl)acetic acid
Description7-Hydroxy-2-oxindole-3-acetic acid belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. (2,7-dihydroxy-3h-indol-3-yl)acetic acid is found in Zea mays. 7-Hydroxy-2-oxindole-3-acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296402 ((2,7-dihydroxy-3h-indol-3-yl)acetic acid)


  Mrv1652310101705532D          

 15 16  0  0  0  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    3.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    2.3061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
M  END
Download

3D MOL for NP0296402 ((2,7-dihydroxy-3h-indol-3-yl)acetic acid)

     RDKit          3D

 24 25  0  0  0  0  0  0  0  0999 V2000
   -3.5182   -1.1004   -1.2114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7549   -0.8683   -0.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6579   -1.8430    0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0442    0.3904   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8785    0.5160    0.7328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3985    1.9534    0.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2255    3.0487    0.7656 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8215    1.9495    0.2203 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3247    0.6284    0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6050    0.2363   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6026    1.1499   -0.5332 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169   -1.1085   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -1.9964    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241   -1.5963    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3072   -0.2695    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503   -2.6578    0.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7881    0.7946   -1.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902    1.1744    0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1425    0.4307    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    3.8741    0.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3668    2.1471   -0.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9214   -1.4135   -0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1539   -3.0467   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -2.3932    0.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 15  5  1  0
 10  9  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  1
  7 20  1  0
 14 24  1  0
 13 23  1  0
 12 22  1  0
 11 21  1  0
M  END
Download

3D SDF for NP0296402 ((2,7-dihydroxy-3h-indol-3-yl)acetic acid)


  Mrv1652310101705532D          

 15 16  0  0  0  0            999 V2000
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    3.2623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    2.3061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296402

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1C(O)=NC2=C1C=CC=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO4/c12-7-3-1-2-5-6(4-8(13)14)10(15)11-9(5)7/h1-3,6,12H,4H2,(H,11,15)(H,13,14)

> <INCHI_KEY>
RBODBEHKWJZUBG-UHFFFAOYSA-N

> <FORMULA>
C10H9NO4

> <MOLECULAR_WEIGHT>
207.185

> <EXACT_MASS>
207.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.695334118166485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,7-dihydroxy-3H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
1.8132547139999997

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.467330469565516

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4576749448980753

> <JCHEM_PKA_STRONGEST_BASIC>
-0.37082090810926027

> <JCHEM_POLAR_SURFACE_AREA>
90.12

> <JCHEM_REFRACTIVITY>
53.16180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2,7-dihydroxy-3H-indol-3-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0296402 ((2,7-dihydroxy-3h-indol-3-yl)acetic acid)

Download
PDB for NP0296402 ((2,7-dihydroxy-3h-indol-3-yl)acetic acid)
HEADER    PROTEIN                                 10-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-17         0                                  
HETATM    1  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.877   4.625   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.401   6.090   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.383   4.305   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    7                                                       
CONECT    4    6    8                                                       
CONECT    5    2    6    9                                                  
CONECT    6    4    5   10                                                  
CONECT    7    3    9   12                                                  
CONECT    8    4   13   14                                                  
CONECT    9    5    7   11                                                  
CONECT   10    6   11   15                                                  
CONECT   11    9   10                                                       
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15   10                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0296402 ((2,7-dihydroxy-3h-indol-3-yl)acetic acid)
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SMILES for NP0296402 ((2,7-dihydroxy-3h-indol-3-yl)acetic acid)
OC(=O)CC1C(O)=NC2=C1C=CC=C2O
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INCHI for NP0296402 ((2,7-dihydroxy-3h-indol-3-yl)acetic acid)
InChI=1S/C10H9NO4/c12-7-3-1-2-5-6(4-8(13)14)10(15)11-9(5)7/h1-3,6,12H,4H2,(H,11,15)(H,13,14)
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View in JSmol
Synonyms
ValueSource
7-Hydroxy-2-oxindole-3-acetateGenerator
2-(2,7-Dihydroxy-3H-indol-3-yl)acetateGenerator
Chemical FormulaC10H9NO4
Average Mass207.1850 Da
Monoisotopic Mass207.05316 Da
IUPAC Name2-(2,7-dihydroxy-3H-indol-3-yl)acetic acid
Traditional Name(2,7-dihydroxy-3H-indol-3-yl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1C(O)=NC2=C1C=CC=C2O
InChI Identifier
InChI=1S/C10H9NO4/c12-7-3-1-2-5-6(4-8(13)14)10(15)11-9(5)7/h1-3,6,12H,4H2,(H,11,15)(H,13,14)
InChI KeyRBODBEHKWJZUBG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Zea maysLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolyl carboxylic acids and derivatives  
Direct ParentIndolyl carboxylic acids and derivatives  
Alternative Parents
Substituents
  • Indolyl carboxylic acid derivative
    • 

  • Indole
    • 

  • Dihydroindole
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Lactam
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Azacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP0.39ALOGPS
logP1.81ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)-0.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity53.16 m³·mol⁻¹ChemAxon
Polarizability19.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0176483  
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 Compound18398273  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]