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Showing NP-Card for Isomaculine (NP0068496)

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Record Information
Version2.0
Created at2022-04-28 13:46:14 UTC
Updated at2022-04-28 13:46:14 UTC
NP-MRD IDNP0068496
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsomaculine
Description2-Methyl-4,12,14-trioxa-2-azatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1(16),3(7),5,9,11(15)-pentaen-8-one belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline. Isomaculine is found in Esenbeckia pilocarpoides. Based on a literature review very few articles have been published on 2-methyl-4,12,14-trioxa-2-azatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1(16),3(7),5,9,11(15)-pentaen-8-one.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0068496 (Isomaculine)


  Mrv1652304282215462D          

 18 21  0  0  0  0            999 V2000
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    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    0.6979    0.0000 N   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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   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
    5.5658    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
  7 15  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
Download

3D MOL for NP0068496 (Isomaculine)

     RDKit          3D

 27 30  0  0  0  0  0  0  0  0999 V2000
    1.0301    2.4486   -0.3297 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0897    1.0259   -0.0341 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846    0.3955    0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084    1.0567    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4969    0.3778    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5126   -0.9760    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2880   -1.6252    0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920   -0.9521    0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207   -1.6280    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371   -2.8380    0.7728 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3135   -0.9689    0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -1.2889    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3619   -0.1339    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5072    0.8363   -0.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2748    0.3924    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8310   -1.3450    0.6383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6482   -0.3286    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8213    0.8096    0.1870 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    2.6400   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5615    3.0169    0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0657    2.8467   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2540    2.1119   -0.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759   -2.6777    0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0303   -2.2846    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4410   -0.1251    0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5340   -0.2397    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9591   -0.5466   -0.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 15  1  0
 15 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 18  1  0
 18 17  1  0
 17 16  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
 14 15  1  0
  3  8  1  0
 16  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 12 24  1  0
 13 25  1  0
  7 23  1  0
 17 26  1  0
 17 27  1  0
  4 22  1  0
M  END
Download

3D SDF for NP0068496 (Isomaculine)


  Mrv1652304282215462D          

 18 21  0  0  0  0            999 V2000
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    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    0.6979    0.0000 N   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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   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
    5.5658    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
  7 15  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(C=CO2)C(=O)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H9NO4/c1-14-9-5-11-10(17-6-18-11)4-8(9)12(15)7-2-3-16-13(7)14/h2-5H,6H2,1H3

> <INCHI_KEY>
FZADKTBPHWEAEJ-UHFFFAOYSA-N

> <FORMULA>
C13H9NO4

> <MOLECULAR_WEIGHT>
243.218

> <EXACT_MASS>
243.053157774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
24.072188992375708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-4,12,14-trioxa-2-azatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),3(7),5,9,11(15)-pentaen-8-one

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.9757248749999992

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9313648145552254

> <JCHEM_POLAR_SURFACE_AREA>
51.91000000000001

> <JCHEM_REFRACTIVITY>
61.492000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-4,12,14-trioxa-2-azatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),3(7),5,9,11(15)-pentaen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0068496 (Isomaculine)

Download
PDB for NP0068496 (Isomaculine)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.390   4.089   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.295   2.843   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.390   1.597   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8                                                       
CONECT   15    7                                                            
CONECT   16    3   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

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3D PDB for NP0068496 (Isomaculine)
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SMILES for NP0068496 (Isomaculine)
CN1C2=C(C=CO2)C(=O)C2=CC3=C(OCO3)C=C12
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INCHI for NP0068496 (Isomaculine)
InChI=1S/C13H9NO4/c1-14-9-5-11-10(17-6-18-11)4-8(9)12(15)7-2-3-16-13(7)14/h2-5H,6H2,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC13H9NO4
Average Mass243.2180 Da
Monoisotopic Mass243.05316 Da
IUPAC Name2-methyl-4,12,14-trioxa-2-azatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),3(7),5,9,11(15)-pentaen-8-one
Traditional Name2-methyl-4,12,14-trioxa-2-azatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),3(7),5,9,11(15)-pentaen-8-one
CAS Registry NumberNot Available
SMILES
CN1C2=C(C=CO2)C(=O)C2=CC3=C(OCO3)C=C12
InChI Identifier
InChI=1S/C13H9NO4/c1-14-9-5-11-10(17-6-18-11)4-8(9)12(15)7-2-3-16-13(7)14/h2-5H,6H2,1H3
InChI KeyFZADKTBPHWEAEJ-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
Esenbeckia pilocarpoidesPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub ClassFuranoquinolines  
Direct ParentFuranoquinolines  
Alternative Parents
Substituents
  • Furanoquinoline
    • 

  • Dihydroquinolone
    • 

  • Dihydroquinoline
    • 

  • Benzodioxole
    • 

  • Furopyridine
    • 

  • Pyridine
    • 

  • Benzenoid
    • 

  • Vinylogous amide
    • 

  • Furan
    • 

  • Heteroaromatic compound
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Acetal
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen 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
logP1.79ALOGPS
logP1.98ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area51.91 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity61.49 m³·mol⁻¹ChemAxon
Polarizability24.07 ųChemAxon
Number of Rings4ChemAxon
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 IDC00026446  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15559957  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available