NP-MRD: Showing NP-Card for {17,18-dimethoxy-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-octaen-20-yl}methanol (NP0232149)

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Record Information

Version

1.0

Created at

2022-09-06 13:17:03 UTC

Updated at

2022-09-06 13:17:03 UTC

NP-MRD ID

NP0232149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{17,18-dimethoxy-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-octaen-20-yl}methanol

Description

Bocconoline 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. {17,18-dimethoxy-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-octaen-20-yl}methanol is found in Tetradium glabrifolium, Glaucium flavum, Hylomecon japonica, Toddalia asiatica, Zanthoxylum ailanthoides, Zanthoxylum mayu, Zanthoxylum nitidum and Zanthoxylum simulans. Bocconoline is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241520042D          

 28 32  0  0  0  0            999 V2000
    2.5176    0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081    0.5938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    0.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    0.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908   -0.0759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9003   -0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    1.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2621    1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947    1.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    1.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    1.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5216    2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    2.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967    2.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    2.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    2.1161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    0.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157   -1.0051    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 15  1  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  2  0  0  0  0
 14 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    5.7703    2.4570   -0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0673    1.2312   -0.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041    1.2383   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0475    2.4271   -0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6821    2.4402   -0.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9839    1.2485   -0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6299    0.0485   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669    0.0317   -0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7244   -1.0910   -0.6989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044   -1.5598   -1.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244   -1.1836   -0.5497 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1686   -1.2554   -1.8916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185   -1.2765   -2.9765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -1.1680    0.4484 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3934   -2.2527    1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    0.0149    0.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941    1.2675    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1073    2.4283    0.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    2.3623    0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0205    1.1588    1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3290    1.0859    1.6152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9678   -0.1089    1.8341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2519   -1.2427    1.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9209   -1.2500    1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3129   -0.0475    1.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0843   -2.3282    1.9040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3771   -1.8511    2.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2621   -0.4551    2.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8539    2.3365   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956    3.1529   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570    2.9306    0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6169    3.3814   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2405    3.4035    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4059   -2.4928   -2.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0766   -1.8569   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7468   -0.7716   -2.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547   -2.0538   -0.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6093   -0.4679   -2.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4271   -2.2141   -1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1157   -2.1974   -3.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6524   -2.4342    1.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567   -3.2107    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9201   -1.9470    2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6477    3.3713    0.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0048    3.2584    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8852    2.0246    1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4995   -2.1816    0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7547   -2.2962    3.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1018   -2.1047    1.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  9  1  0
  9 10  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  1  0
 14 11  1  0
 11 12  1  0
 12 13  1  0
 16 25  1  0
 25 24  2  0
 24 23  1  0
 23 22  2  0
 22 28  1  0
 28 27  1  0
 27 26  1  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
  4  3  1  0
 18 17  1  0
 11  7  1  0
 20 25  1  0
 26 23  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
  5 33  1  0
  4 32  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 11 37  1  1
 12 38  1  0
 12 39  1  0
 13 40  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
M  END


  Mrv1533004241520042D          

 28 32  0  0  0  0            999 V2000
    2.5176    0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081    0.5938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927    0.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8794    2.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736    2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8774    1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    0.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4908   -0.0759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9003   -0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716    1.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2621    1.6527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4947    1.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9043    1.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    1.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    1.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    1.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5216    2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1121    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9063    2.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967    2.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    2.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3017    2.1161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6067    1.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    0.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061   -0.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5157   -1.0051    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 15  1  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  2  0  0  0  0
 14 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C(C=C1)C1=C(N(C)C2CO)C2=CC3=C(OCO3)C=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H21NO5/c1-23-16(10-24)20-13(6-7-17(25-2)22(20)26-3)14-5-4-12-8-18-19(28-11-27-18)9-15(12)21(14)23/h4-9,16,24H,10-11H2,1-3H3

> <INCHI_KEY>
GKBDCSXIKLSKMH-UHFFFAOYSA-N

> <FORMULA>
C22H21NO5

> <MOLECULAR_WEIGHT>
379.412

> <EXACT_MASS>
379.14197278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.833570268776555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{17,18-dimethoxy-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-octaen-20-yl}methanol

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
3.146775088999999

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.898618469699972

> <JCHEM_PKA_STRONGEST_BASIC>
0.3208057277838049

> <JCHEM_POLAR_SURFACE_AREA>
60.39

> <JCHEM_REFRACTIVITY>
105.28340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{17,18-dimethoxy-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-octaen-20-yl}methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       4.700   0.033   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.802   1.108   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.284   0.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.386   1.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.006   3.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.108   4.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.591   3.918   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.971   2.426   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.869   1.351   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.249  -0.142   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.147  -1.217   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.454   2.009   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.556   3.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.524   3.676   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.421   2.601   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.939   3.017   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.837   1.942   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.354   2.358   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.974   3.851   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.076   4.926   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.558   4.510   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.661   5.585   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.143   5.169   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.563   3.950   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.132   2.519   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.052   1.536   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.665  -0.801   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.563  -1.876   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12                                                            
CONECT   14    5   15   23                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   14                                                       
CONECT   24   19   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18                                                       
CONECT   27    3   28                                                       
CONECT   28   27                                                            
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

{17,18-dimethoxy-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-octaen-20-yl}methanol

Traditional Name

{17,18-dimethoxy-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-octaen-20-yl}methanol

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C=C1)C1=C(N(C)C2CO)C2=CC3=C(OCO3)C=C2C=C1

InChI Identifier

InChI=1S/C22H21NO5/c1-23-16(10-24)20-13(6-7-17(25-2)22(20)26-3)14-5-4-12-8-18-19(28-11-27-18)9-15(12)21(14)23/h4-9,16,24H,10-11H2,1-3H3

InChI Key

GKBDCSXIKLSKMH-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
Euodia fargesii	LOTUS Database	35616633
Glaucium flavum	LOTUS Database	35616633
Hylomecon japonica	LOTUS Database	35616633
Toddalia asiatica	LOTUS Database	35616633
Zanthoxylum ailanthoides	LOTUS Database	35616633
Zanthoxylum mayu	LOTUS Database	35616633
Zanthoxylum nitidum	LOTUS Database	35616633
Zanthoxylum simulans	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
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Tertiary amine
1,2-aminoalcohol
Azacycle
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Alcohol
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
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	3.51	ALOGPS
logP	3.15	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.9	ChemAxon
pKa (Strongest Basic)	0.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.28 m³·mol⁻¹	ChemAxon
Polarizability	40.83 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

181121

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-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-octaen-20-yl}methanol (NP0232149)

MOL for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

3D MOL for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

3D SDF for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

3D-SDF for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

PDB for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

3D PDB for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

SMILES for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

INCHI for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

Structure for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)

3D Structure for NP0232149 ({17,18-dimethoxy-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-octaen-20-yl}methanol)