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Showing NP-Card for acetylindoxyl (NP0193687)

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Record Information
Version2.0
Created at2022-09-04 11:12:37 UTC
Updated at2022-09-04 11:12:37 UTC
NP-MRD IDNP0193687
Secondary Accession NumbersNone
Natural Product Identification
Common Nameacetylindoxyl
DescriptionN-acetylindoxyl belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. N-acetylindoxyl is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. acetylindoxyl is found in Lactarius deliciosus. acetylindoxyl was first documented in 1954 (PMID: 13159343). Based on a literature review very few articles have been published on N-acetylindoxyl (PMID: 3941406).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0193687 (acetylindoxyl)


  Mrv1652309042213122D          

 13 14  0  0  0  0            999 V2000
    0.0768   -2.3215    0.0000 C   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
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   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
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  4 13  1  0  0  0  0
M  END
Download

3D MOL for NP0193687 (acetylindoxyl)

     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
    2.9308   -1.0760   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990    0.2754    0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2830    1.2096    0.1209 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0419    0.6710    0.0663 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6066    1.9643    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7581    2.0158    0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5763    3.1322    0.3056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149    0.7167    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976    0.1854    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6366   -1.1704   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244   -1.9525   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476   -1.4569   -0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0794   -0.0768   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978   -1.5831   -1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0687   -1.0711   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871   -1.7322    0.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2766    2.8089    0.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5685    2.9969    0.2914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3146    0.8850    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6121   -1.6026   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5825   -3.0504   -0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -2.0892   -0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  4  1  0
 13  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  7 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0193687 (acetylindoxyl)


  Mrv1652309042213122D          

 13 14  0  0  0  0            999 V2000
    0.0768   -2.3215    0.0000 C   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
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 N   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 O   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
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  4 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193687

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N1C=C(O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO2/c1-7(12)11-6-10(13)8-4-2-3-5-9(8)11/h2-6,13H,1H3

> <INCHI_KEY>
NNJXIAOPPYUVAX-UHFFFAOYSA-N

> <FORMULA>
C10H9NO2

> <MOLECULAR_WEIGHT>
175.187

> <EXACT_MASS>
175.063328534

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.030739033363265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3-hydroxy-1H-indol-1-yl)ethan-1-one

> <JCHEM_LOGP>
1.0882515966666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.090309285684793

> <JCHEM_PKA_STRONGEST_BASIC>
-3.432699119242051

> <JCHEM_POLAR_SURFACE_AREA>
42.230000000000004

> <JCHEM_REFRACTIVITY>
48.39570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
acetylindoxyl

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0193687 (acetylindoxyl)

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PDB for NP0193687 (acetylindoxyl)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       2.126  -2.549   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.650   1.408   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8    4                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0193687 (acetylindoxyl)
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SMILES for NP0193687 (acetylindoxyl)
CC(=O)N1C=C(O)C2=CC=CC=C12
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INCHI for NP0193687 (acetylindoxyl)
InChI=1S/C10H9NO2/c1-7(12)11-6-10(13)8-4-2-3-5-9(8)11/h2-6,13H,1H3
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View in JSmol
Synonyms
ValueSource
1-Acetyl-1H-indol-3-olChEBI
AcetylindoxylChEBI
Chemical FormulaC10H9NO2
Average Mass175.1870 Da
Monoisotopic Mass175.06333 Da
IUPAC Name1-(3-hydroxy-1H-indol-1-yl)ethan-1-one
Traditional Nameacetylindoxyl
CAS Registry NumberNot Available
SMILES
CC(=O)N1C=C(O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C10H9NO2/c1-7(12)11-6-10(13)8-4-2-3-5-9(8)11/h2-6,13H,1H3
InChI KeyNNJXIAOPPYUVAX-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
Lactarius deliciosusLOTUS 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
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Acetamide
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP1.09ChemAxon
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area42.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.4 m³·mol⁻¹ChemAxon
Polarizability18.03 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 IDNot Available
Chemspider ID388767  
KEGG Compound IDC02298  
BioCyc IDN-ACETYLINDOXYL  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439701  
PDB IDNot Available
ChEBI ID15363  
Good Scents IDNot Available
References
General References
  1. Muller-Uri C, Singer EA, Fleischhacker W: Synthesis of alkyl-substituted arecoline derivatives as gamma-aminobutyric acid uptake inhibitors. J Med Chem. 1986 Jan;29(1):125-32. doi: 10.1021/jm00151a020. [PubMed:3941406  ] 
  2. BEEVERS H, FRENCH RC: Oxidation of N-acetylindoxyl by an enzyme from plants. Arch Biochem Biophys. 1954 Jun;50(2):427-39. doi: 10.1016/0003-9861(54)90059-4. [PubMed:13159343  ] 
  3. LOTUS database [Link]