NP-MRD: Showing NP-Card for 17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium (NP0257306)

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Record Information

Version

2.0

Created at

2022-09-07 22:23:54 UTC

Updated at

2022-09-07 22:23:54 UTC

NP-MRD ID

NP0257306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium

Description

17,18-Dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-21-ium belongs to the class of organic compounds known as quaternary benzophenanthridine alkaloids. These are alkaloids containing a quaternary N-demethylbenzophenanthridine skeleton, where the nitrogen atom of the phenanthridine moiety is part of four bonds. 17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium is found in Chelidonium majus, Garcinia lucida and Zanthoxylum riedelianum. Based on a literature review very few articles have been published on 17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(21),2,4(8),9,11,13,15,17,19-nonaen-21-ium.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082200232D          

 30 34  0  0  0  0            999 V2000
   -0.3633   -2.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1595   -2.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347   -3.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -3.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327   -4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2232   -3.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194   -2.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098   -2.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -2.3708    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.9945   -1.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078   -3.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021   -3.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -2.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867   -3.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9905   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4001   -4.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -4.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0154   -4.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2192   -5.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134   -5.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039   -5.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172   -6.5912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212   -4.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174   -3.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138   -3.8932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1188   -3.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4840   -2.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252   -2.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -1.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2271   -1.4779    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  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  2  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 11 24  2  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
  7 28  2  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  CHG  1   9   1
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    6.4592    1.8603    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8278    0.6025    0.4700 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531    0.5365    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255    1.6956    0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289    1.6561    0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084    0.4181    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4191   -0.7380    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7807   -1.9384    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4086   -2.0712   -0.0730 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.1125   -3.3976   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690   -0.9197   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6589   -0.9390   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387   -2.1155   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7446   -2.0933   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4505   -0.9380   -0.4146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7635    0.2456   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831    0.2747   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7519    1.4897   -0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5148    2.7467   -0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218    3.0396    1.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0357    4.2849    1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1559    2.3075    1.9834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3891    1.4981   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593    0.3298   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8238   -1.2500   -0.5105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9527   -2.6761   -0.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6140   -3.1642   -0.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7870   -0.6889    0.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5570   -1.8337    0.2973 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1089   -2.4773   -0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9941    2.5199    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5285    1.6804    0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4829    2.3008   -0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1870    2.6767    0.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8525    2.6052    0.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374   -2.8879    0.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -3.5777   -1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8405   -4.0113   -0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588   -3.9951    0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9304   -3.0439   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2856    1.1914   -0.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298    3.6305   -0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373    2.7987   -1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8550    4.8279    2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1152    4.0368    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    4.9600    0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0930    2.4545   -0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3106   -2.9434   -1.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6277   -2.9776    0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8985   -1.9492   -1.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7986   -3.5440   -0.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2260   -2.4975   -0.6906 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  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 24  2  0
 24 23  1  0
 23 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 27  1  0
 27 26  1  0
 26 25  1  0
 14 13  1  0
 13 12  2  0
  7 28  2  0
 28 29  1  0
 29 30  1  0
 28  3  1  0
 24  6  1  0
 12 17  1  0
 12 11  1  0
 25 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  5 35  1  0
  8 36  1  0
 10 37  1  0
 10 38  1  0
 10 39  1  0
 23 47  1  0
 19 42  1  0
 19 43  1  0
 21 44  1  0
 21 45  1  0
 21 46  1  0
 16 41  1  0
 26 48  1  0
 26 49  1  0
 13 40  1  0
 30 50  1  0
 30 51  1  0
 30 52  1  0
M  CHG  1   9   1
M  END


  Mrv1652309082200232D          

 30 34  0  0  0  0            999 V2000
   -0.3633   -2.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1595   -2.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6347   -3.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -3.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6327   -4.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2232   -3.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194   -2.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6098   -2.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -2.3708    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.9945   -1.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6078   -3.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021   -3.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -2.8173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7867   -3.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9905   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4001   -4.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -4.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0154   -4.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2192   -5.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0134   -5.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039   -5.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2172   -6.5912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2212   -4.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174   -3.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138   -3.8932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1188   -3.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4840   -2.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2252   -2.5006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -1.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2271   -1.4779    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  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  2  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 11 24  2  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
  7 28  2  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  CHG  1   9   1
M  END
> <DATABASE_ID>
NP0257306

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(C=[N+](C)C3=C2C=C(CC(C)=O)C2=CC4=C(OCO4)C=C32)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H22NO5/c1-13(26)7-14-8-17-15-5-6-20(27-3)24(28-4)19(15)11-25(2)23(17)18-10-22-21(9-16(14)18)29-12-30-22/h5-6,8-11H,7,12H2,1-4H3/q+1

> <INCHI_KEY>
KOSVXGIMZXQLHB-UHFFFAOYSA-N

> <FORMULA>
C24H22NO5

> <MOLECULAR_WEIGHT>
404.441

> <EXACT_MASS>
404.149249233

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
44.22153110530331

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-ium

> <JCHEM_LOGP>
-0.9146988288050784

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.89405185099712

> <JCHEM_PKA_STRONGEST_BASIC>
-4.386712170546141

> <JCHEM_POLAR_SURFACE_AREA>
57.870000000000005

> <JCHEM_REFRACTIVITY>
112.8366

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.678  -3.834   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.298  -5.327   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.185  -5.743   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.565  -7.236   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.048  -7.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.150  -6.577   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.770  -5.084   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.872  -4.009   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.354  -4.426   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0       7.456  -3.350   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.735  -5.918   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.217  -6.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.319  -5.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.802  -5.676   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.182  -7.168   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.080  -8.244   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.598  -7.827   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.495  -8.902   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.876 -10.395   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.358 -10.811   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.461  -9.736   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.739 -12.304   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.013  -8.486   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.632  -6.993   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.719  -7.267   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.288  -5.836   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.104  -4.853   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.287  -4.668   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.907  -3.175   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.424  -2.759   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   24                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24                                                       
CONECT   24   23    6   11                                                  
CONECT   25   15   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   14                                                       
CONECT   28    7    3   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₂NO₅

Average Mass

404.4410 Da

Monoisotopic Mass

404.14925 Da

IUPAC Name

17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-ium

Traditional Name

17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-ium

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(C=[N+](C)C3=C2C=C(CC(C)=O)C2=CC4=C(OCO4)C=C32)=C1OC

InChI Identifier

InChI=1S/C24H22NO5/c1-13(26)7-14-8-17-15-5-6-20(27-3)24(28-4)19(15)11-25(2)23(17)18-10-22-21(9-16(14)18)29-12-30-22/h5-6,8-11H,7,12H2,1-4H3/q+1

InChI Key

KOSVXGIMZXQLHB-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
Chelidonium majus	LOTUS Database	35616633
Garcinia lucida	LOTUS Database	35616633
Zanthoxylum riedelianum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quaternary benzophenanthridine alkaloids. These are alkaloids containing a quaternary N-demethylbenzophenanthridine skeleton, where the nitrogen atom of the phenanthridine moiety is part of four bonds.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Quaternary benzophenanthridine alkaloids

Direct Parent

Quaternary benzophenanthridine alkaloids

Alternative Parents

Substituents

Quaternary benzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Isoquinoline
Naphthalene
Quinoline
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Pyridine
Pyridinium
Heteroaromatic compound
Ketone
Acetal
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Aldehyde
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen 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	-0.91	ChemAxon
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.87 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.84 m³·mol⁻¹	ChemAxon
Polarizability	44.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

4983432

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6482972

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium (NP0257306)

MOL for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

3D MOL for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

3D SDF for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

3D-SDF for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

PDB for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

3D PDB for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

SMILES for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

INCHI for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

Structure for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)

3D Structure for NP0257306 (17,18-dimethoxy-21-methyl-11-(2-oxopropyl)-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2(10),3,8,11,14(19),15,17,20-nonaen-21-ium)