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Showing NP-Card for 3-Methyldioxyindole (NP0085701)

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Record Information
Version2.0
Created at2022-04-29 06:11:07 UTC
Updated at2022-04-29 06:11:07 UTC
NP-MRD IDNP0085701
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methyldioxyindole
Description3-Methyldioxyindole 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-Methyldioxyindole is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyldioxyindole is found in Tripterygium wilfordii . 3-Methyldioxyindole was first documented in 1989 (PMID: 2796599). A methylindole that is 1,3-dihydro-2H-indol-2-one substituted by methyl and a hydroxy group at position 3.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0085701 (3-Methyldioxyindole)


  Mrv0541 02231219542D          

 12 13  0  0  0  0            999 V2000
   22.5167  -23.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1550  -24.9596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8485  -25.6235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5949  -23.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8485  -24.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3300  -24.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0679  -25.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0679  -24.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3533  -25.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3533  -24.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6388  -25.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6388  -24.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0085701 (3-Methyldioxyindole)

     RDKit          3D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.8886    1.1542   -0.5371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    0.1657    0.4450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6137    0.4983    1.7623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -1.1922    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042   -1.6067    0.1524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5486   -1.9036   -0.3152 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5790   -1.0316   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9395   -1.2467   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8208   -0.2060   -0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4247    1.0339    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980    1.2412    0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1780    0.1985    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6978    1.7310   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1361    1.9026   -0.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690    0.5902   -1.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4531    0.0427    2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5128   -2.8952   -0.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524   -2.2055   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8888   -0.3170   -0.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1040    1.8623    0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125    2.1839    0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  2  1  0
 12  7  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  6 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for NP0085701 (3-Methyldioxyindole)


  Mrv0541 02231219542D          

 12 13  0  0  0  0            999 V2000
   22.5167  -23.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1550  -24.9596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8485  -25.6235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5949  -23.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8485  -24.2957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3300  -24.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0679  -25.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0679  -24.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3533  -25.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3533  -24.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6388  -25.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6388  -24.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0085701

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO2/c1-9(12)6-4-2-3-5-7(6)10-8(9)11/h2-5,12H,1H3,(H,10,11)

> <INCHI_KEY>
XCHBYBKNFIOSBB-UHFFFAOYSA-N

> <FORMULA>
C9H9NO2

> <MOLECULAR_WEIGHT>
163.1733

> <EXACT_MASS>
163.063328537

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.363818068069442

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3-methyl-2,3-dihydro-1H-indol-2-one

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
0.7896576123333333

> <ALOGPS_LOGS>
-1.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19063668345774

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.780694099537866

> <JCHEM_PKA_STRONGEST_BASIC>
-4.068271597352317

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
45.63640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-methyloxindole

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0085701 (3-Methyldioxyindole)

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PDB for NP0085701 (3-Methyldioxyindole)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      42.031 -44.449   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      43.223 -46.591   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      40.784 -47.831   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      40.310 -43.886   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      40.784 -45.352   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      41.683 -46.591   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.327 -47.361   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.327 -45.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.993 -48.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.993 -45.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.659 -47.361   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.659 -45.821   0.000  0.00  0.00           C+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    6    7                                                       
CONECT    4    5                                                            
CONECT    5    1    4    6    8                                             
CONECT    6    2    3    5                                                  
CONECT    7    3    8    9                                                  
CONECT    8    5    7   10                                                  
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0085701 (3-Methyldioxyindole)
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SMILES for NP0085701 (3-Methyldioxyindole)
CC1(O)C(=O)NC2=CC=CC=C12
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INCHI for NP0085701 (3-Methyldioxyindole)
InChI=1S/C9H9NO2/c1-9(12)6-4-2-3-5-7(6)10-8(9)11/h2-5,12H,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
1,3-Dihydro-3-hydroxy-3-methyl-2H-indol-2-oneChEBI
3-Hydroxy-3-methyloxindoleKegg
3-Hydroxy-3-methyl-2-indolinoneHMDB
3-Hydroxy-3-methyl-oxindoleHMDB
3-MethyldioxyindoleChEBI
Chemical FormulaC9H9NO2
Average Mass163.1733 Da
Monoisotopic Mass163.06333 Da
IUPAC Name3-hydroxy-3-methyl-2,3-dihydro-1H-indol-2-one
Traditional Name3-hydroxy-3-methyloxindole
CAS Registry NumberNot Available
SMILES
CC1(O)C(=O)NC2=CC=CC=C12
InChI Identifier
InChI=1S/C9H9NO2/c1-9(12)6-4-2-3-5-7(6)10-8(9)11/h2-5,12H,1H3,(H,10,11)
InChI KeyXCHBYBKNFIOSBB-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tripterygium wilfordiiPlant
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
    • 

  • Tertiary alcohol
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP0.88ALOGPS
logP0.79ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)11.78ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.64 m³·mol⁻¹ChemAxon
Polarizability16.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004186  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023329  
KNApSAcK IDNot Available
Chemspider ID133151  
KEGG Compound IDC05834  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7024  
PubChem Compound151066  
PDB IDNot Available
ChEBI ID28254  
Good Scents IDNot Available
References
General References
  1. Albrecht CF, Chorn DJ, Wessels PL: Detection of 3-hydroxy-3-methyloxindole in human urine. Life Sci. 1989;45(12):1119-26. doi: 10.1016/0024-3205(89)90169-0. [PubMed:2796599  ]