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Showing NP-Card for (3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol (NP0197005)

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Record Information
Version2.0
Created at2022-09-04 15:11:25 UTC
Updated at2022-09-04 15:11:26 UTC
NP-MRD IDNP0197005
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol
DescriptionFumaridine belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. (3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol is found in Dactylicapnos torulosa, Fumaria densiflora, Fumaria parviflora and Fumaria vaillantii. (3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol was first documented in 2018 (PMID: 30265534). Based on a literature review very few articles have been published on Fumaridine (PMID: 35745580).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0197005 ((3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol)


  Mrv1652309042217112D          

 29 32  0  0  0  0            999 V2000
    7.2256    0.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6736    0.2603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    0.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3146   -0.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076   -0.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2527    0.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6117    1.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1637    1.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9707    1.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922    2.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7278    2.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5852    1.9309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    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  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 29  1  0  0  0  0
M  END
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3D MOL for NP0197005 ((3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol)

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3D SDF for NP0197005 ((3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol)

  Mrv1652309042217112D          

 29 32  0  0  0  0            999 V2000
    7.2256    0.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6736    0.2603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8666    0.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3146   -0.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5076   -0.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2527    0.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    1.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6117    1.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1637    1.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9707    1.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922    2.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7278    2.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5852    1.9309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    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  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197005

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2\C(=C\C3=CC4=C(OCO4)C=C3CCN(C)C)N=C(O)C2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H24N2O5/c1-24(2)8-7-13-10-18-19(29-12-28-18)11-14(13)9-16-15-5-6-17(26-3)21(27-4)20(15)22(25)23-16/h5-6,9-11H,7-8,12H2,1-4H3,(H,23,25)/b16-9-

> <INCHI_KEY>
ZMAHFZSTFDAVRW-SXGWCWSVSA-N

> <FORMULA>
C22H24N2O5

> <MOLECULAR_WEIGHT>
396.443

> <EXACT_MASS>
396.168521881

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.66822247904984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1Z)-1-({6-[2-(dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methylidene)-4,5-dimethoxy-1H-isoindol-3-ol

> <JCHEM_LOGP>
0.5414327659503119

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.373608791142549

> <JCHEM_PKA_STRONGEST_BASIC>
9.135587291608642

> <JCHEM_POLAR_SURFACE_AREA>
72.75

> <JCHEM_REFRACTIVITY>
111.63159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-({6-[2-(dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0197005 ((3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol)
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PDB for NP0197005 ((3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      13.488   1.630   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.457   0.486   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.951   0.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.921  -0.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.414  -0.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.938   1.446   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.969   2.591   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.475   2.271   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.506   3.415   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.012   3.095   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.199   3.925   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.825   5.331   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       6.692   3.604   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       6.531   6.693   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       6.531   8.233   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    6   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   19   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   18                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

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3D PDB for NP0197005 ((3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol)
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SMILES for NP0197005 ((3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol)
COC1=CC=C2\C(=C\C3=CC4=C(OCO4)C=C3CCN(C)C)N=C(O)C2=C1OC
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INCHI for NP0197005 ((3z)-3-({6-[2-(dimethylamino)ethyl]-2h-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol)
InChI=1S/C22H24N2O5/c1-24(2)8-7-13-10-18-19(29-12-28-18)11-14(13)9-16-15-5-6-17(26-3)21(27-4)20(15)22(25)23-16/h5-6,9-11H,7-8,12H2,1-4H3,(H,23,25)/b16-9-
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SynonymsNot Available
Chemical FormulaC22H24N2O5
Average Mass396.4430 Da
Monoisotopic Mass396.16852 Da
IUPAC Name(1Z)-1-({6-[2-(dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methylidene)-4,5-dimethoxy-1H-isoindol-3-ol
Traditional Name(3Z)-3-({6-[2-(dimethylamino)ethyl]-2H-1,3-benzodioxol-5-yl}methylidene)-6,7-dimethoxyisoindol-1-ol
CAS Registry NumberNot Available
SMILES
COC1=CC=C2\C(=C\C3=CC4=C(OCO4)C=C3CCN(C)C)N=C(O)C2=C1OC
InChI Identifier
InChI=1S/C22H24N2O5/c1-24(2)8-7-13-10-18-19(29-12-28-18)11-14(13)9-16-15-5-6-17(26-3)21(27-4)20(15)22(25)23-16/h5-6,9-11H,7-8,12H2,1-4H3,(H,23,25)/b16-9-
InChI KeyZMAHFZSTFDAVRW-SXGWCWSVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dactylicapnos torulosaLOTUS Database
Fumaria densifloraLOTUS Database
Fumaria parvifloraLOTUS Database
Fumaria vaillantiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIsoindoles and derivatives  
Sub ClassIsoindolines  
Direct ParentIsoindolones  
Alternative Parents
Substituents
  • Isoindolone
    • 

  • Benzodioxole
    • 

  • Isoindole
    • 

  • Phenethylamine
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Aralkylamine
    • 

  • Benzenoid
    • 

  • Amino acid or derivatives
    • 

  • Carboxamide group
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Secondary carboxylic acid amide
    • 

  • Lactam
    • 

  • Acetal
    • 

  • Carboxylic acid derivative
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen 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
logP0.54ChemAxon
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.75 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity111.63 m³·mol⁻¹ChemAxon
Polarizability43.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5020547  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6537302  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Batool S, Javed MR, Aslam S, Noor F, Javed HMF, Seemab R, Rehman A, Aslam MF, Paray BA, Gulnaz A: Network Pharmacology and Bioinformatics Approach Reveals the Multi-Target Pharmacological Mechanism of Fumaria indica in the Treatment of Liver Cancer. Pharmaceuticals (Basel). 2022 May 25;15(6):654. doi: 10.3390/ph15060654. [PubMed:35745580  ] 
  2. Yao T, Guo Z, Liang X, Qi L: Regio- and Stereoselective Electrophilic Cyclization Approach for the Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine, Fumaridine, 8-Oxypseudoplamatine, and 2- O-(Methyloxy)fagaronine. J Org Chem. 2018 Nov 2;83(21):13370-13380. doi: 10.1021/acs.joc.8b02154. Epub  2018 Oct 12. [PubMed:30265534  ] 
  3. LOTUS database [Link]