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Showing NP-Card for 3-ethyl-3-methoxyindol-2-ol (NP0255929)

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Record Information
Version2.0
Created at2022-09-07 20:35:52 UTC
Updated at2022-09-07 20:35:52 UTC
NP-MRD IDNP0255929
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-ethyl-3-methoxyindol-2-ol
Description3-Ethyl-1,3-dihydro-3-methoxy-2H-indol-2-one, also known as 3-ethyl-3-methoxy-1,3-dihydro-indol-2-one, belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. 3-Ethyl-1,3-dihydro-3-methoxy-2H-indol-2-one 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. 3-ethyl-3-methoxyindol-2-ol was first documented in 1979 (PMID: 374323). Based on a literature review very few articles have been published on 3-ethyl-1,3-dihydro-3-methoxy-2H-indol-2-one.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0255929 (3-ethyl-3-methoxyindol-2-ol)


  Mrv1652309072222352D          

 14 15  0  0  0  0            999 V2000
    0.4243   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    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
    1.4743   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2948   -2.2053    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
   -0.1712   -0.6979    0.0000 O   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
    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  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
Download

3D MOL for NP0255929 (3-ethyl-3-methoxyindol-2-ol)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -1.7548   -0.6911    1.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4466   -1.3538    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7732   -0.3285   -0.3976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6775    0.7046   -0.5428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    1.7266   -1.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -1.0366   -1.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4441   -1.5839   -2.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7821   -1.0789   -1.8021 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4731   -0.4358   -0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -0.2272   -0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2227    0.4469    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3062    0.9370    1.5535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735    0.7244    1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5290    0.0386    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958   -1.1761    2.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9966    0.3683    1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646   -0.8352    2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384   -2.2637    0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863   -1.6382   -0.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    2.1112   -0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9864    1.4261   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430    2.5651   -1.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8961   -0.9609   -3.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5249   -0.6282   -1.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2765    0.6023    0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6311    1.4783    2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2345    1.1087    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  4  5  1  0
  3  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  3  1  0
 14  9  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  2 19  1  0
  5 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 13 27  1  0
M  END
Download

3D SDF for NP0255929 (3-ethyl-3-methoxyindol-2-ol)


  Mrv1652309072222352D          

 14 15  0  0  0  0            999 V2000
    0.4243   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4243   -1.7779    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
    1.4743   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2948   -2.2053    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
   -0.1712   -0.6979    0.0000 O   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
    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  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255929

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(OC)C(O)=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO2/c1-3-11(14-2)8-6-4-5-7-9(8)12-10(11)13/h4-7H,3H2,1-2H3,(H,12,13)

> <INCHI_KEY>
ICBZGIGZAFEKFH-UHFFFAOYSA-N

> <FORMULA>
C11H13NO2

> <MOLECULAR_WEIGHT>
191.23

> <EXACT_MASS>
191.094628663

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.188927635986076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethyl-3-methoxy-3H-indol-2-ol

> <JCHEM_LOGP>
2.6827631813333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9183092060903606

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2216493795719091

> <JCHEM_POLAR_SURFACE_AREA>
41.82

> <JCHEM_REFRACTIVITY>
55.66670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-ethyl-3-methoxyindol-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0255929 (3-ethyl-3-methoxyindol-2-ol)

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PDB for NP0255929 (3-ethyl-3-methoxyindol-2-ol)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.792  -4.859   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.792  -3.319   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  O   UNK     0       2.752  -3.956   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.284  -4.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  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    6   14                                             
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9    3                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0255929 (3-ethyl-3-methoxyindol-2-ol)
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SMILES for NP0255929 (3-ethyl-3-methoxyindol-2-ol)
CCC1(OC)C(O)=NC2=CC=CC=C12
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INCHI for NP0255929 (3-ethyl-3-methoxyindol-2-ol)
InChI=1S/C11H13NO2/c1-3-11(14-2)8-6-4-5-7-9(8)12-10(11)13/h4-7H,3H2,1-2H3,(H,12,13)
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Synonyms
ValueSource
3-Ethyl-3-methoxy-1,3-dihydro-indol-2-oneChEBI
3-Ethyl-3-methoxy-1H-indol-2-oneChEBI
3-Ethyl-3-methoxyindolin-2-oneChEBI
Chemical FormulaC11H13NO2
Average Mass191.2300 Da
Monoisotopic Mass191.09463 Da
IUPAC Name3-ethyl-3-methoxy-3H-indol-2-ol
Traditional Name3-ethyl-3-methoxyindol-2-ol
CAS Registry NumberNot Available
SMILES
CCC1(OC)C(O)=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C11H13NO2/c1-3-11(14-2)8-6-4-5-7-9(8)12-10(11)13/h4-7H,3H2,1-2H3,(H,12,13)
InChI KeyICBZGIGZAFEKFH-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene  to form 2,3-dihydroindole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolines  
Direct ParentIndolines  
Alternative Parents
Substituents
  • Dihydroindole
    • 

  • Benzenoid
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Dialkyl ether
    • 

  • Ether
    • 

  • Azacycle
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP2.68ChemAxon
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)-0.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.82 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.67 m³·mol⁻¹ChemAxon
Polarizability20.19 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 ID15305007  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20379047  
PDB IDNot Available
ChEBI ID141381  
Good Scents IDNot Available
References
General References
  1. Westley JW, Evans RH Jr, Sello LH, Troupe N, Liu CM, Blount JF: Isolation and characterization of antibiotic X-14547A, a novel monocarboxylic acid ionophore produced by Streptomyces antibioticus NRRL 8167. J Antibiot (Tokyo). 1979 Feb;32(2):100-7. doi: 10.7164/antibiotics.32.100. [PubMed:374323  ] 
  2. LOTUS database [Link]