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Showing NP-Card for Taraxacine B (NP0068723)

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Record Information
Version2.0
Created at2022-04-28 13:59:08 UTC
Updated at2022-04-28 13:59:08 UTC
NP-MRD IDNP0068723
Secondary Accession NumbersNone
Natural Product Identification
Common NameTaraxacine B
Description1-Methoxy-9H-pyrido[3,4-b]indole-3-carboxylic acid belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Taraxacine B is found in Taraxacum formosanum. 1-Methoxy-9H-pyrido[3,4-b]indole-3-carboxylic acid is a very strong basic compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0068723 (Taraxacine B)


  Mrv1533004181500132D          

 18 20  0  0  0  0            999 V2000
    1.2637   -4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -3.5424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -2.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410   -3.0712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3724    0.0377    0.0000 O   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  2  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
  7  8  1  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
  8 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
  7 15  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
Download

3D MOL for NP0068723 (Taraxacine B)

     RDKit          3D

 28 30  0  0  0  0  0  0  0  0999 V2000
    3.7731   -2.1302    0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3765   -1.9976    0.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7425   -0.7992    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4036    0.3397   -0.0639 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8088    1.5157   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6103    2.7234   -0.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518    2.7003   -0.5683 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460    3.9108   -0.8640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4313    1.5674   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2980    0.4268   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579   -0.7580    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869   -1.6929    0.3460 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8254   -1.1884    0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1050   -1.6960    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2192   -0.9098    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714    0.4374   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7890    0.9338   -0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6476    0.1679   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -3.1011    0.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829   -2.0926    1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -1.3236   -0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1453    4.1717   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625    2.5025   -0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3868   -2.6895    0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2458   -2.7427    0.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2176   -1.3208    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9550    1.0434   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6508    2.0014   -0.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
  5  6  1  0
  6  8  1  0
  6  7  2  0
 11  3  1  0
 14 13  1  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  9 23  1  0
 12 24  1  0
 17 28  1  0
 16 27  1  0
 15 26  1  0
 14 25  1  0
  8 22  1  0
M  END
Download

3D SDF for NP0068723 (Taraxacine B)


  Mrv1533004181500132D          

 18 20  0  0  0  0            999 V2000
    1.2637   -4.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7117   -3.5424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4146   -2.1447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4765   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056   -1.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4675   -2.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4410   -3.0712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -2.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3724    0.0377    0.0000 O   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  2  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
  7  8  1  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
  8 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
  7 15  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068723

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=NC(=CC2=C1NC1=C2C=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H10N2O3/c1-18-12-11-8(6-10(15-12)13(16)17)7-4-2-3-5-9(7)14-11/h2-6,14H,1H3,(H,16,17)

> <INCHI_KEY>
IZGILNCXLRBSAJ-UHFFFAOYSA-N

> <FORMULA>
C13H10N2O3

> <MOLECULAR_WEIGHT>
242.234

> <EXACT_MASS>
242.06914219

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
24.51492515185638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methoxy-9H-pyrido[3,4-b]indole-3-carboxylic acid

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
1.2602187729151573

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.906198302688654

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2189708015280174

> <JCHEM_PKA_STRONGEST_BASIC>
5.018392338044862

> <JCHEM_POLAR_SURFACE_AREA>
75.21

> <JCHEM_REFRACTIVITY>
64.9762

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methoxy-9H-pyrido[3,4-b]indole-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0068723 (Taraxacine B)

Download
PDB for NP0068723 (Taraxacine B)
HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       2.359  -7.757   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.328  -6.612   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.804  -5.148   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.774  -4.003   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.250  -2.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.756  -2.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.787  -3.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.327  -3.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.357  -2.219   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.863  -2.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.339  -4.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.309  -5.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.802  -4.828   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.557  -5.733   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.311  -4.828   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.219  -1.394   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.287  -1.715   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.695   0.070   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    3    7                                                  
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

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3D PDB for NP0068723 (Taraxacine B)
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SMILES for NP0068723 (Taraxacine B)
COC1=NC(=CC2=C1NC1=C2C=CC=C1)C(O)=O
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INCHI for NP0068723 (Taraxacine B)
InChI=1S/C13H10N2O3/c1-18-12-11-8(6-10(15-12)13(16)17)7-4-2-3-5-9(7)14-11/h2-6,14H,1H3,(H,16,17)
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View in JSmol
Synonyms
ValueSource
1-Methoxy-9H-pyrido[3,4-b]indole-3-carboxylateGenerator
Chemical FormulaC13H10N2O3
Average Mass242.2340 Da
Monoisotopic Mass242.06914 Da
IUPAC Name1-methoxy-9H-pyrido[3,4-b]indole-3-carboxylic acid
Traditional Name1-methoxy-9H-pyrido[3,4-b]indole-3-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=NC(=CC2=C1NC1=C2C=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C13H10N2O3/c1-18-12-11-8(6-10(15-12)13(16)17)7-4-2-3-5-9(7)14-11/h2-6,14H,1H3,(H,16,17)
InChI KeyIZGILNCXLRBSAJ-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
Taraxacum formosanumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassPyridoindoles  
Direct ParentBeta carbolines  
Alternative Parents
Substituents
  • Beta-carboline
    • 

  • Indole
    • 

  • Pyridine carboxylic acid
    • 

  • Pyridine carboxylic acid or derivatives
    • 

  • Alkyl aryl ether
    • 

  • Pyridine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen 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
logP2.64ALOGPS
logP1.26ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)5.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.21 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.98 m³·mol⁻¹ChemAxon
Polarizability24.51 ųChemAxon
Number of Rings3ChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10999180  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available