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Showing NP-Card for (3s)-6-bromo-3-methylindole-2,3-diol (NP0239408)

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Record Information
Version2.0
Created at2022-09-06 23:00:15 UTC
Updated at2022-09-06 23:00:15 UTC
NP-MRD IDNP0239408
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s)-6-bromo-3-methylindole-2,3-diol
DescriptionZINC44713103 belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. (3s)-6-bromo-3-methylindole-2,3-diol is found in Anabaena constricta. Based on a literature review very few articles have been published on ZINC44713103.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0239408 ((3s)-6-bromo-3-methylindole-2,3-diol)


  Mrv1652309072201002D          

 13 14  0  0  1  0            999 V2000
    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  1  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
    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
    4.0668    0.1271    0.0000 Br  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
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
Download

3D MOL for NP0239408 ((3s)-6-bromo-3-methylindole-2,3-diol)

     RDKit          3D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.6417   -1.5749   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0181   -0.3063   -0.6207 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0625   -0.3989   -2.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    0.8967   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1238    1.1193   -0.5063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9606    1.6788    0.3960 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    1.1333    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366    1.5903    1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825    0.8291    1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2715    1.5305    1.8221 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6883   -0.4062    0.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5190   -0.8644   -0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3465   -0.0909   -0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6832   -1.6004   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -1.6432    1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162   -2.4255   -0.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603   -1.2296   -2.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5678    1.9959   -0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4866    2.5634    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066   -0.9649    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -1.8322   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13  2  1  0
 13  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  5 18  1  0
  8 19  1  0
 11 20  1  0
 12 21  1  0
M  END
Download

3D SDF for NP0239408 ((3s)-6-bromo-3-methylindole-2,3-diol)


  Mrv1652309072201002D          

 13 14  0  0  1  0            999 V2000
    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  1  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
    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
    4.0668    0.1271    0.0000 Br  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
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239408

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(O)C(O)=NC2=CC(Br)=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C9H8BrNO2/c1-9(13)6-3-2-5(10)4-7(6)11-8(9)12/h2-4,13H,1H3,(H,11,12)/t9-/m0/s1

> <INCHI_KEY>
IGRQAUGYEAXYJY-VIFPVBQESA-N

> <FORMULA>
C9H8BrNO2

> <MOLECULAR_WEIGHT>
242.072

> <EXACT_MASS>
240.973842

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
20.17365357812159

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-6-bromo-3-methyl-3H-indole-2,3-diol

> <JCHEM_LOGP>
2.285866908

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.408548775429534

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1306762908079255

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5034054798835651

> <JCHEM_POLAR_SURFACE_AREA>
52.82

> <JCHEM_REFRACTIVITY>
54.01430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-6-bromo-3-methylindole-2,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0239408 ((3s)-6-bromo-3-methylindole-2,3-diol)

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PDB for NP0239408 ((3s)-6-bromo-3-methylindole-2,3-diol)
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  -3.319   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.752  -3.956   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0       7.591   0.237   0.000  0.00  0.00          Br+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   13                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7    2                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0239408 ((3s)-6-bromo-3-methylindole-2,3-diol)
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SMILES for NP0239408 ((3s)-6-bromo-3-methylindole-2,3-diol)
C[C@@]1(O)C(O)=NC2=CC(Br)=CC=C12
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INCHI for NP0239408 ((3s)-6-bromo-3-methylindole-2,3-diol)
InChI=1S/C9H8BrNO2/c1-9(13)6-3-2-5(10)4-7(6)11-8(9)12/h2-4,13H,1H3,(H,11,12)/t9-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H8BrNO2
Average Mass242.0720 Da
Monoisotopic Mass240.97384 Da
IUPAC Name(3S)-6-bromo-3-methyl-3H-indole-2,3-diol
Traditional Name(3S)-6-bromo-3-methylindole-2,3-diol
CAS Registry NumberNot Available
SMILES
C[C@@]1(O)C(O)=NC2=CC(Br)=CC=C12
InChI Identifier
InChI=1S/C9H8BrNO2/c1-9(13)6-3-2-5(10)4-7(6)11-8(9)12/h2-4,13H,1H3,(H,11,12)/t9-/m0/s1
InChI KeyIGRQAUGYEAXYJY-VIFPVBQESA-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
Anabaena constrictaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct Parent3-alkylindoles  
Alternative Parents
Substituents
  • 3-alkylindole
    • 

  • Aryl bromide
    • 

  • Aryl halide
    • 

  • Benzenoid
    • 

  • Tertiary alcohol
    • 

  • Cyclic carboximidic acid
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Azacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organobromide
    • 

  • Organohalogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen 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
logP2.29ChemAxon
pKa (Strongest Acidic)2.13ChemAxon
pKa (Strongest Basic)-0.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.01 m³·mol⁻¹ChemAxon
Polarizability20.17 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 ID113059170  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124428810  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]