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Showing NP-Card for 4-hydroxyindole-3-carbaldehyde (NP0259422)

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Record Information
Version2.0
Created at2022-09-08 01:17:39 UTC
Updated at2022-09-08 01:17:39 UTC
NP-MRD IDNP0259422
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-hydroxyindole-3-carbaldehyde
Description4-Hydroxyindole-3-carbaldehyde, also known as 4-HO-i3cho or 4-hydroxy-3-formylindole, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 4-Hydroxyindole-3-carbaldehyde is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 4-hydroxyindole-3-carbaldehyde is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on 4-hydroxyindole-3-carbaldehyde.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0259422 (4-hydroxyindole-3-carbaldehyde)


  Mrv1652309082203172D          

 12 13  0  0  0  0            999 V2000
    0.0768   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   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  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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  3 12  1  0  0  0  0
  6 12  1  0  0  0  0
M  END
Download

3D MOL for NP0259422 (4-hydroxyindole-3-carbaldehyde)

     RDKit          3D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -3.7930    0.4079    0.5889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6137    0.8003    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -0.1845    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704   -1.5623    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4692   -2.1033    0.0726 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4765   -1.1533   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8464   -1.1629   -0.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    0.0184   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695    1.2146   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086    1.2391   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112    2.4244    0.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    0.0528    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4361    1.8601    0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6448   -2.0432    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514   -3.1221    0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3056   -2.1385   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6040   -0.0038   -0.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784    2.1736   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    3.2828    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  2  0
 12  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  3 12  1  0
 11 19  1  0
  5 15  1  0
  4 14  1  0
  2 13  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0259422 (4-hydroxyindole-3-carbaldehyde)


  Mrv1652309082203172D          

 12 13  0  0  0  0            999 V2000
    0.0768   -2.3215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   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  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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  3 12  1  0  0  0  0
  6 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259422

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C2C(NC=C2C=O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO2/c11-5-6-4-10-7-2-1-3-8(12)9(6)7/h1-5,10,12H

> <INCHI_KEY>
QLBZIZLLMNWTHG-UHFFFAOYSA-N

> <FORMULA>
C9H7NO2

> <MOLECULAR_WEIGHT>
161.16

> <EXACT_MASS>
161.047678469

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.847535476974382

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-1H-indole-3-carbaldehyde

> <JCHEM_LOGP>
1.480944832

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.276929664709087

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.992842829840157

> <JCHEM_PKA_STRONGEST_BASIC>
-5.656868091370776

> <JCHEM_POLAR_SURFACE_AREA>
53.09

> <JCHEM_REFRACTIVITY>
45.7094

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-1H-indole-3-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0259422 (4-hydroxyindole-3-carbaldehyde)

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PDB for NP0259422 (4-hydroxyindole-3-carbaldehyde)
HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0       0.143  -4.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    3    6                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0259422 (4-hydroxyindole-3-carbaldehyde)
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SMILES for NP0259422 (4-hydroxyindole-3-carbaldehyde)
OC1=C2C(NC=C2C=O)=CC=C1
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INCHI for NP0259422 (4-hydroxyindole-3-carbaldehyde)
InChI=1S/C9H7NO2/c11-5-6-4-10-7-2-1-3-8(12)9(6)7/h1-5,10,12H
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View in JSmol
Synonyms
ValueSource
4-HO-I3choChEBI
4-Hydroxy-3-formylindoleChEBI
4-Hydroxy-3-indolecarbaldehydeChEBI
4-Hydroxy-3-indolecarboxaldehydeChEBI
4-Hydroxyindole-3-carboxaldehydeChEBI
Chemical FormulaC9H7NO2
Average Mass161.1600 Da
Monoisotopic Mass161.04768 Da
IUPAC Name4-hydroxy-1H-indole-3-carbaldehyde
Traditional Name4-hydroxy-1H-indole-3-carbaldehyde
CAS Registry NumberNot Available
SMILES
OC1=C2C(NC=C2C=O)=CC=C1
InChI Identifier
InChI=1S/C9H7NO2/c11-5-6-4-10-7-2-1-3-8(12)9(6)7/h1-5,10,12H
InChI KeyQLBZIZLLMNWTHG-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
Arabidopsis thalianaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassHydroxyindoles  
Direct ParentHydroxyindoles  
Alternative Parents
Substituents
  • Hydroxyindole
    • 

  • Indole
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Aryl-aldehyde
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aldehyde
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen 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
logP1.48ChemAxon
pKa (Strongest Acidic)8.99ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.71 m³·mol⁻¹ChemAxon
Polarizability15.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 ID7991032  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9815282  
PDB IDNot Available
ChEBI ID91162  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]