Np mrd loader

Showing NP-Card for 5-Hydroxyindole (NP0083451)

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Record Information
Version2.0
Created at2022-04-29 04:29:31 UTC
Updated at2022-04-29 04:29:31 UTC
NP-MRD IDNP0083451
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxyindole
Description5-Hydroxyindole, also known as indol-5-ol, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 5-Hydroxyindole is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hydroxyindole is found in Homo sapiens (Urine). 5-Hydroxyindole was first documented in 1965 (PMID: 5294372). These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole (PMID: 21784895) (PMID: 5294373).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083451 (5-Hydroxyindole)


  Mrv1652304272018442D          

 10 11  0  0  0  0            999 V2000
   -1.0093   -1.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809   -0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3884   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2247   -2.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -2.8334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
Download

3D MOL for NP0083451 (5-Hydroxyindole)

     RDKit          3D

 17 18  0  0  0  0  0  0  0  0999 V2000
    3.2108   -0.7345   -0.6004 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9162   -0.3006   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7229    1.0246   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501    1.4935    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691    0.6717    0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9924    0.8915    0.3836 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635   -0.2583    0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -1.2166   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709   -0.6550   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8119   -1.1255   -0.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415   -1.0871    0.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    1.7168    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868    2.5237    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3986    1.8160    0.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7512   -0.3682    0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -2.2402   -0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9350   -2.1518   -0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 10  2  0
 10  9  1  0
  9  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  8  9  1  0
  1 11  1  0
 10 17  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
  4 13  1  0
  3 12  1  0
M  END
Download

3D SDF for NP0083451 (5-Hydroxyindole)


  Mrv1652304272018442D          

 10 11  0  0  0  0            999 V2000
   -1.0093   -1.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809   -0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3884   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2247   -2.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532   -2.8334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083451

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(NC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H

> <INCHI_KEY>
LMIQERWZRIFWNZ-UHFFFAOYSA-N

> <FORMULA>
C8H7NO

> <MOLECULAR_WEIGHT>
133.1473

> <EXACT_MASS>
133.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.801860314432467

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indol-5-ol

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.768442487333333

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.622731498087642

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.572356139390685

> <JCHEM_PKA_STRONGEST_BASIC>
-5.507064086661161

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
39.12539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxyindol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0083451 (5-Hydroxyindole)

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PDB for NP0083451 (5-Hydroxyindole)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -1.884  -3.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.204  -1.800   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.310   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.405   1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.725  -2.752   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.405  -1.246   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.419  -3.783   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.060  -0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.060   0.770   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -0.099  -5.289   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    4    6                                                       
CONECT    4    3    9                                                       
CONECT    5    6    7                                                       
CONECT    6    3    5    8                                                  
CONECT    7    1    5   10                                                  
CONECT    8    2    6    9                                                  
CONECT    9    4    8                                                       
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0083451 (5-Hydroxyindole)
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SMILES for NP0083451 (5-Hydroxyindole)
OC1=CC2=C(NC=C2)C=C1
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INCHI for NP0083451 (5-Hydroxyindole)
InChI=1S/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
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View in JSmol
Synonyms
ValueSource
5-Hydroxy-1H-indoleChEBI
indol-5-OlChEBI
Chemical FormulaC8H7NO
Average Mass133.1473 Da
Monoisotopic Mass133.05276 Da
IUPAC Name1H-indol-5-ol
Traditional Name5-hydroxyindol
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(NC=C2)C=C1
InChI Identifier
InChI=1S/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
InChI KeyLMIQERWZRIFWNZ-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
Homo sapiens (Urine)Animalia
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-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen 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
logP1.53ALOGPS
logP1.77ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.57ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.13 m³·mol⁻¹ChemAxon
Polarizability13.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059805  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-16174  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16054  
PDB IDNot Available
ChEBI ID89649  
Good Scents IDNot Available
References
General References
  1. Aronov PA, Luo FJ, Plummer NS, Quan Z, Holmes S, Hostetter TH, Meyer TW: Colonic contribution to uremic solutes. J Am Soc Nephrol. 2011 Sep;22(9):1769-76. doi: 10.1681/ASN.2010121220. Epub 2011  Jul 22. [PubMed:21784895  ] 
  2. Ashcroft GW, Eccleston D, Crawford TB: 5-hydroxyindole metabolism in rat brain. A study of intermediate metabolism using the technique of tryptophan loading. I. Methods. J Neurochem. 1965 Jun;12(6):483-92. doi: 10.1111/j.1471-4159.1965.tb06775.x. [PubMed:5294372  ] 
  3. Eccleston D, Ashcroft GW, Crawford TB: 5-hydroxyindole metabolism in rat brain. A study of intermediate metabolism using the technique of tryptophan loading. II. Applications and drug studies. J Neurochem. 1965 Jun;12(6):493-503. doi: 10.1111/j.1471-4159.1965.tb06776.x. [PubMed:5294373  ]