NP-MRD: Showing NP-Card for (20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene (NP0323913)

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Record Information

Version

2.0

Created at

2022-09-12 03:38:59 UTC

Updated at

2022-09-12 03:39:00 UTC

NP-MRD ID

NP0323913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene

Description

(20R)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(13),2,4(8),9,11,14(19),15,17-octaene belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety. (20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene is found in Argemone mexicana, Macleaya microcarpa and Zanthoxylum leprieurii. Based on a literature review very few articles have been published on (20R)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]Henicosa-1(13),2,4(8),9,11,14(19),15,17-octaene.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205392D          

 28 32  0  0  1  0            999 V2000
    7.2621    1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    1.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    0.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    0.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    3.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2850    3.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    2.6753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1061    3.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    4.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081    2.4521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5176    3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947    1.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967    0.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    0.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    0.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5216    0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    1.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    2.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    0.9298    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  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 16 25  2  0  0  0  0
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -6.2122    1.3263    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2583    0.2816    0.2168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264    0.5892   -0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4904    1.8450   -0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596    2.1286   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2394    1.0945   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6639   -0.1643   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9841   -0.4282    0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4333   -1.7059    0.4886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -2.0371    1.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -1.3341   -0.1290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6110   -1.8920   -1.3797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9801   -3.2213   -1.4284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791   -0.8876    0.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2401   -1.6444    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0809    0.3577   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822    1.3803   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    2.6232   -0.8143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0178    2.8347   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167    1.8622   -0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2733    2.0817   -0.4805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1604    1.0834   -0.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6839   -0.1472    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054   -0.4142    0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4395    0.5869   -0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7664   -0.9378    0.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9757   -0.2012    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5626    1.0247   -0.1095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9234    2.1888    0.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2221    1.0119    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1501    1.6587   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2588    2.6357   -0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8328    3.1051   -0.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7000   -3.1441    1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6152   -1.7740    2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3665   -1.4853    2.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -2.0751    0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256   -3.3924   -1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085   -3.5378   -2.5009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3522   -3.8491   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3276   -1.8097    2.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504   -1.0634    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4815   -2.6745    1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001    3.4299   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121    3.8179   -1.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6511    3.0559   -0.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0503   -1.4030    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2631   -0.0883    1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7853   -0.6923   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 25  2  0
 25 24  1  0
 24 23  2  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 22  1  0
 22 21  2  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3  8  1  0
  8  9  1  0
  9 10  1  0
  8  7  2  0
  7 11  1  0
 17 16  1  0
  7  6  1  0
 20 25  1  0
 22 23  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 11 37  1  1
 15 41  1  0
 15 42  1  0
 15 43  1  0
 24 47  1  0
 27 48  1  0
 27 49  1  0
 21 46  1  0
 19 45  1  0
 18 44  1  0
  5 33  1  0
  4 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
M  END


  Mrv1652309122205392D          

 28 32  0  0  1  0            999 V2000
    7.2621    1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    1.9694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    0.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    0.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908    3.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2850    3.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    2.6753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1061    3.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157    4.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081    2.4521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5176    3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947    1.0765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967    0.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    0.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    0.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5216    0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    1.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    2.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    1.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    2.2233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    0.9298    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  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 16 25  2  0  0  0  0
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0323913

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1N(C)C2=C3C=C4OCOC4=CC3=CC=C2C2=CC=C(OC)C(OC)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H21NO5/c1-23-20-14(6-5-12-9-17-18(10-15(12)20)28-11-27-17)13-7-8-16(24-2)21(25-3)19(13)22(23)26-4/h5-10,22H,11H2,1-4H3/t22-/m1/s1

> <INCHI_KEY>
LVWAKZBZWYHYCJ-JOCHJYFZSA-N

> <FORMULA>
C22H21NO5

> <MOLECULAR_WEIGHT>
379.412

> <EXACT_MASS>
379.14197278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.91711771816849

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(20R)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaene

> <JCHEM_LOGP>
4.056012592999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.007650466944404

> <JCHEM_POLAR_SURFACE_AREA>
49.39

> <JCHEM_REFRACTIVITY>
105.102

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(20R)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      13.556   2.601   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.454   3.676   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.971   3.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.591   1.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.108   1.351   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.006   2.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.386   3.918   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.869   4.335   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.249   5.827   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.732   6.244   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.284   4.994   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.665   6.486   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.563   7.562   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.802   4.577   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.700   5.653   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.421   3.085   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.524   2.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.143   0.517   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.661   0.100   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.558   1.176   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.076   0.759   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.974   1.835   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.354   3.327   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.837   3.744   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.939   2.668   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.052   4.150   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.132   3.166   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.563   1.736   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   17                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   25                                                  
CONECT   17   16    6   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   16   20                                                  
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   22                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁NO₅

Average Mass

379.4120 Da

Monoisotopic Mass

379.14197 Da

IUPAC Name

(20R)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaene

Traditional Name

(20R)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18-octaene

CAS Registry Number

Not Available

SMILES

CO[C@H]1N(C)C2=C3C=C4OCOC4=CC3=CC=C2C2=CC=C(OC)C(OC)=C12

InChI Identifier

InChI=1S/C22H21NO5/c1-23-20-14(6-5-12-9-17-18(10-15(12)20)28-11-27-17)13-7-8-16(24-2)21(25-3)19(13)22(23)26-4/h5-10,22H,11H2,1-4H3/t22-/m1/s1

InChI Key

LVWAKZBZWYHYCJ-JOCHJYFZSA-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
Argemone mexicana	LOTUS Database	35616633
Macleaya microcarpa	LOTUS Database	35616633
Zanthoxylum leprieurii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydrobenzophenanthridine alkaloids. These are alkaloids containing a dihydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a dihydrophenanthridine moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Dihydrobenzophenanthridine alkaloids

Direct Parent

Dihydrobenzophenanthridine alkaloids

Alternative Parents

Substituents

Dihydrobenzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Naphthalene
Quinoline
Benzodioxole
Anisole
Dialkylarylamine
Alkyl aryl ether
Benzenoid
Organoheterocyclic compound
Azacycle
Ether
Acetal
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
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	4.06	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.1 m³·mol⁻¹	ChemAxon
Polarizability	40.92 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

92144424

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene (NP0323913)

MOL for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

3D MOL for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

3D SDF for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

3D-SDF for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

PDB for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

3D PDB for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

SMILES for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

INCHI for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

Structure for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)

3D Structure for NP0323913 ((20r)-17,18,20-trimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]henicosa-1(13),2,4(8),9,11,14,16,18-octaene)