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Showing NP-Card for 6-Hydroxyindole-3-carboxaldehyde (NP0077859)

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Record Information
Version1.0
Created at2022-04-28 23:00:35 UTC
Updated at2022-04-28 23:00:35 UTC
NP-MRD IDNP0077859
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-Hydroxyindole-3-carboxaldehyde
Description2-(2-Formyl-6-hydroxy-1H-indol-3-yl)acetic acid 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. 6-Hydroxyindole-3-carboxaldehyde is found in Haliclona oculata. Based on a literature review very few articles have been published on 2-(2-formyl-6-hydroxy-1H-indol-3-yl)acetic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0077859 (6-Hydroxyindole-3-carboxaldehyde)


  Mrv1652304292201002D          

 16 17  0  0  0  0            999 V2000
    3.3523    1.9354    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    0.6979    0.0000 C   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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  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
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  1 16  1  0  0  0  0
M  END
Download

3D MOL for NP0077859 (6-Hydroxyindole-3-carboxaldehyde)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -2.8273   -1.3854    1.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009   -2.0120    1.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -1.3124    0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477   -1.8662    0.4655 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170   -0.9311   -0.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -0.9540   -0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301    0.1949   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2912    0.0809   -1.7972 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2963    1.3545   -1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249    1.4047   -0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5257    0.2362   -0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6980    0.0183    0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7494    1.0512    0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    0.8802   -0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7736   -0.0388   -1.0577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584    1.7185   -0.1988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128   -3.0568    1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6804   -2.8689    0.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -1.8795   -0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1227    0.2173   -1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7319    2.2486   -1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4770    2.3405   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767    0.9924    1.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063    2.0508    0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502    1.5160    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 13 12  1  0
 12  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
  3  2  1  0
  2  1  2  0
 11 12  1  0
 11  5  1  0
 16 25  1  0
 13 23  1  0
 13 24  1  0
  4 18  1  0
  6 19  1  0
  8 20  1  0
  9 21  1  0
 10 22  1  0
  2 17  1  0
M  END
Download

3D SDF for NP0077859 (6-Hydroxyindole-3-carboxaldehyde)


  Mrv1652304292201002D          

 16 17  0  0  0  0            999 V2000
    3.3523    1.9354    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    0.6979    0.0000 C   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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   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  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  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
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  1 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077859

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC1=C(NC2=CC(O)=CC=C12)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H9NO4/c13-5-10-8(4-11(15)16)7-2-1-6(14)3-9(7)12-10/h1-3,5,12,14H,4H2,(H,15,16)

> <INCHI_KEY>
YCEJVJKGXJWMSA-UHFFFAOYSA-N

> <FORMULA>
C11H9NO4

> <MOLECULAR_WEIGHT>
219.196

> <EXACT_MASS>
219.053157774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.11300976441011

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-formyl-6-hydroxy-1H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.0386942449999998

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.512036488804084

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8890206562087823

> <JCHEM_PKA_STRONGEST_BASIC>
-5.529610313239382

> <JCHEM_POLAR_SURFACE_AREA>
90.39

> <JCHEM_REFRACTIVITY>
56.8945

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-formyl-6-hydroxy-1H-indol-3-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0077859 (6-Hydroxyindole-3-carboxaldehyde)

Download
PDB for NP0077859 (6-Hydroxyindole-3-carboxaldehyde)
HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.887   0.957   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.333  -1.652   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.090   4.177   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
CONECT    1    2    6   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   14                                                            
CONECT   16    1                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0077859 (6-Hydroxyindole-3-carboxaldehyde)
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SMILES for NP0077859 (6-Hydroxyindole-3-carboxaldehyde)
OC(=O)CC1=C(NC2=CC(O)=CC=C12)C=O
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INCHI for NP0077859 (6-Hydroxyindole-3-carboxaldehyde)
InChI=1S/C11H9NO4/c13-5-10-8(4-11(15)16)7-2-1-6(14)3-9(7)12-10/h1-3,5,12,14H,4H2,(H,15,16)
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View in JSmol
Synonyms
ValueSource
2-(2-Formyl-6-hydroxy-1H-indol-3-yl)acetateGenerator
Chemical FormulaC11H9NO4
Average Mass219.1960 Da
Monoisotopic Mass219.05316 Da
IUPAC Name2-(2-formyl-6-hydroxy-1H-indol-3-yl)acetic acid
Traditional Name(2-formyl-6-hydroxy-1H-indol-3-yl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC1=C(NC2=CC(O)=CC=C12)C=O
InChI Identifier
InChI=1S/C11H9NO4/c13-5-10-8(4-11(15)16)7-2-1-6(14)3-9(7)12-10/h1-3,5,12,14H,4H2,(H,15,16)
InChI KeyYCEJVJKGXJWMSA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Haliclona oculataAnimalia
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolyl carboxylic acids and derivatives  
Direct ParentIndole-3-acetic acid derivatives  
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
    • 

  • Hydroxyindole
    • 

  • 3-alkylindole
    • 

  • Indole
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Aryl-aldehyde
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Aldehyde
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • 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
logP1.47ALOGPS
logP1.04ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.39 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.89 m³·mol⁻¹ChemAxon
Polarizability21.11 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00041286  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound59921197  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available