NP-MRD: Showing NP-Card for 16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium (NP0249778)

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Record Information

Version

2.0

Created at

2022-09-07 12:26:16 UTC

Updated at

2022-09-07 12:26:16 UTC

NP-MRD ID

NP0249778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium

Description

16,17-Dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-3(11),4(8),9,14,16,18-hexaen-1-ium belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. 16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium is found in Fumaria officinalis. 16,17-Dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]Henicosa-3(11),4(8),9,14,16,18-hexaen-1-ium is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191518512D          

 26 30  0  0  0  0            999 V2000
    8.8716   -0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4700    0.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6451    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2435    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4186    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0170    1.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921    1.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688    1.1583    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.3672    1.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9439    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5206    0.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222   -0.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7471   -0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9953    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3969   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6234   -1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4483   -1.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988   -0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6739   -0.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681   -0.0491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1530    1.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6957    0.4752    0.0000 C   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  1  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
  8 10  1  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
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  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
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
 22 26  2  0  0  0  0
M  CHG  1   8   1
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
   -5.7445    0.1702    2.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1937   -0.3450    1.3108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9149   -0.0885    0.8576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0426    0.7381    1.5652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    0.9934    1.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3494    0.4328   -0.0414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2120   -0.3871   -0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912   -0.6618   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3641   -1.4941   -1.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8648   -2.0508   -2.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048    0.6632   -0.5794 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4619   -0.5999   -1.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8701   -0.9308   -1.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5925   -1.6451   -1.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9197   -1.9553   -1.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5610   -1.5564   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8262   -0.8446    0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5048   -0.5253    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    0.2401    1.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9328    1.2274    0.3291 N   0  0  1  0  0  4  0  0  0  0  0  0
    1.9396    1.9346   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4070    2.1837    1.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    1.8630    1.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6893   -0.5607    1.3761 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0207   -0.6802    0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599   -1.7082   -0.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1976   -0.1080    3.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6901    1.2869    2.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8185   -0.0753    2.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226    1.1598    2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8934   -0.8398   -1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0357   -2.7191   -1.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4454   -1.2568   -2.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6649   -2.5394   -2.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.4171   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367   -1.4801   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542   -0.6006   -2.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340   -1.9783   -2.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4496   -2.5258   -2.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3378    0.8064    1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0157   -0.4725    1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736    2.0951    0.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0628    1.4850   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5035    2.9613   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3083    3.1626    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1665    2.3838    2.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4561    2.8096    2.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495    1.3939    2.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7146   -1.0333    1.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3857    0.2552    0.4232 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  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 18 17  1  0
 17 16  2  0
 16 26  1  0
 26 25  1  0
 25 24  1  0
 16 15  1  0
 15 14  2  0
  8  3  1  0
 20 11  1  0
 24 17  1  0
 23  5  1  0
 14 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  7 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  6
 12 36  1  0
 12 37  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 25 50  1  0
 15 39  1  0
 14 38  1  0
M  CHG  1  20   1
M  END


  Mrv1533004191518512D          

 26 30  0  0  0  0            999 V2000
    8.8716   -0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4700    0.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6451    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2435    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4186    1.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0170    1.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921    1.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7688    1.1583    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.3672    1.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9439    1.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5206    0.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222   -0.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7471   -0.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9953    0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3969   -0.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2218   -0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6234   -1.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4483   -1.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4988   -0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6739   -0.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681   -0.0491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    0.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1530    1.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6957    0.4752    0.0000 C   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  1  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
  8 10  1  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
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  2  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
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
 22 26  2  0  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0249778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1OC)C1CC3=C(C[N+]1(C)CC2)C1=C(OCO1)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C21H24NO4/c1-22-7-6-14-9-19(23-2)20(24-3)10-15(14)17(22)8-13-4-5-18-21(16(13)11-22)26-12-25-18/h4-5,9-10,17H,6-8,11-12H2,1-3H3/q+1

> <INCHI_KEY>
MTDQIOGTAVVTIY-UHFFFAOYSA-N

> <FORMULA>
C21H24NO4

> <MOLECULAR_WEIGHT>
354.425

> <EXACT_MASS>
354.169984677

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.565281678199064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14(19),15,17-hexaen-1-ium

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
-1.0757858971384118

> <ALOGPS_LOGS>
-6.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.868759170723415

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.099714067371472

> <JCHEM_PKA_STRONGEST_BASIC>
-4.366598168765996

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
110.1096

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.04e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14(19),15,17-hexaen-1-ium

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      16.560  -0.622   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.811   0.723   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.271   0.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.521   2.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.981   2.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.232   3.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.692   3.484   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       8.902   2.162   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0       8.152   3.507   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.362   2.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.572   0.864   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.321  -0.482   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.861  -0.505   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.651   0.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.191   0.793   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.941  -0.552   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.481  -0.575   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.230  -1.920   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      15.770  -1.944   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.531  -1.803   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.991  -1.780   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.242  -0.435   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.740  -0.092   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.603   1.442   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.019   2.047   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.032   0.887   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   26                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14    5   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    3   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   12   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   11   22                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄NO₄

Average Mass

354.4250 Da

Monoisotopic Mass

354.16998 Da

IUPAC Name

16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14(19),15,17-hexaen-1-ium

Traditional Name

16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9,14(19),15,17-hexaen-1-ium

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1OC)C1CC3=C(C[N+]1(C)CC2)C1=C(OCO1)C=C3

InChI Identifier

InChI=1S/C21H24NO4/c1-22-7-6-14-9-19(23-2)20(24-3)10-15(14)17(22)8-13-4-5-18-21(16(13)11-22)26-12-25-18/h4-5,9-10,17H,6-8,11-12H2,1-3H3/q+1

InChI Key

MTDQIOGTAVVTIY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Fumaria officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Protoberberine alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Protoberberine alkaloids and derivatives

Alternative Parents

Substituents

Protoberberine skeleton
Tetrahydroprotoberberine skeleton
Tetrahydroisoquinoline
Benzodioxole
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tetraalkylammonium salt
Quaternary ammonium salt
Acetal
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.05	ALOGPS
logP	-1.1	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	18.1	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.11 m³·mol⁻¹	ChemAxon
Polarizability	39.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101723814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium (NP0249778)

MOL for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

3D MOL for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

3D SDF for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

3D-SDF for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

PDB for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

3D PDB for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

SMILES for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

INCHI for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

Structure for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)

3D Structure for NP0249778 (16,17-dimethoxy-1-methyl-5,7-dioxa-1-azapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10,14(19),15,17-hexaen-1-ium)