NP-MRD: Showing NP-Card for broussonpapyrine (NP0040212)

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Record Information

Version

2.0

Created at

2021-06-20 22:26:17 UTC

Updated at

2021-06-30 00:13:59 UTC

NP-MRD ID

NP0040212

Secondary Accession Numbers

None

Natural Product Identification

Common Name

broussonpapyrine

Provided By

JEOL Database JEOL Logo

Description

15,16-Dimethoxy-21-methyl-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 phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included. broussonpapyrine was first documented in 2011 (Ishihara, Y., et al.). Based on a literature review very few articles have been published on 15,16-dimethoxy-21-methyl-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 3D SDF PDB SMILES InChI


  Mrv1652306212100263D          

 44 48  0  0  0  0            999 V2000
   -3.1114    0.5486   -6.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2158    1.0660   -6.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    0.2042   -5.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306   -1.1651   -5.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -1.9482   -4.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6619   -1.3778   -3.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -2.2036   -2.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -1.7556   -0.9448 N   0  3  0  0  0  4  0  0  0  0  0  0
    0.5869   -2.7072    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -0.4524   -0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954    0.0031    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -0.8212    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286   -0.2712    1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791    1.0725    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    1.9362    1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0422    1.4070    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    2.2959   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    1.8404   -1.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457    0.4737   -1.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160    0.0021   -2.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377    0.7697   -4.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    2.1261   -4.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    2.5116   -5.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    1.4102    2.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1006    0.1130    3.3541 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4956   -0.9642    2.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043   -0.1657   -7.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.3853   -7.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5048   -1.6554   -5.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2995   -3.3509    0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -2.1680    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4773   -3.3221    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824   -1.8864    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979    3.0063    1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0650    2.6202   -2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710    3.3355   -4.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    2.8833   -5.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7871    1.7019   -5.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197   -0.0608    4.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1811    0.1062    3.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20  6  1  0  0  0  0
  5  6  2  0  0  0  0
 16 11  1  0  0  0  0
  6  7  1  0  0  0  0
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  3  4  2  0  0  0  0
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  7  8  2  0  0  0  0
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  3  2  1  0  0  0  0
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  4 30  1  0  0  0  0
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  7 32  1  0  0  0  0
 17 38  1  0  0  0  0
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 12 36  1  0  0  0  0
 15 37  1  0  0  0  0
 25 43  1  0  0  0  0
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 23 40  1  0  0  0  0
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  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
M  CHG  1   8   1
M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -3.1114    0.5486   -6.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2158    1.0660   -6.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    0.2042   -5.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306   -1.1651   -5.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -1.9482   -4.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6619   -1.3778   -3.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -2.2036   -2.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -1.7556   -0.9448 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5869   -2.7072    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -0.4524   -0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954    0.0031    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -0.8212    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286   -0.2712    1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791    1.0725    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    1.9362    1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0422    1.4070    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1341    2.5116   -5.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    1.4102    2.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1006    0.1130    3.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.9642    2.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043   -0.1657   -7.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.3853   -7.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4410   -3.2677   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -3.3509    0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -2.1680    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4773   -3.3221    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1811    0.1062    3.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  2  0
 20  6  1  0
  5  6  2  0
 16 11  1  0
  6  7  1  0
 11 12  1  0
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  3  4  2  0
 14 15  2  0
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 14 13  1  0
  7  8  2  0
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 19 20  1  0
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 21  3  1  0
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 19 10  1  0
  3  2  1  0
 10 11  2  0
 21 22  1  0
 22 23  1  0
 16 17  2  0
  2  1  1  0
  4  5  1  0
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  4 30  1  0
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 17 38  1  0
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 12 36  1  0
 15 37  1  0
 25 43  1  0
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 23 40  1  0
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 23 42  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
M  CHG  1   8   1
M  END


  Mrv1652306212100263D          

 44 48  0  0  0  0            999 V2000
   -3.1114    0.5486   -6.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2158    1.0660   -6.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    0.2042   -5.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306   -1.1651   -5.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -1.9482   -4.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6619   -1.3778   -3.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -2.2036   -2.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -1.7556   -0.9448 N   0  3  0  0  0  4  0  0  0  0  0  0
    0.5869   -2.7072    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -0.4524   -0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6791    1.0725    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    1.9362    1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0422    1.4070    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4160    0.0021   -2.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377    0.7697   -4.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    2.1261   -4.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    2.5116   -5.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    1.4102    2.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5783   -2.1680    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
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 18 19  2  0  0  0  0
 20  6  1  0  0  0  0
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  7 32  1  0  0  0  0
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  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
M  CHG  1   8   1
M  END
> <DATABASE_ID>
NP0040212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2C(=C1[H])C([H])=[N+](C1=C3C([H])=C4OC([H])([H])OC4=C([H])C3=C([H])C([H])=C21)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H18NO4/c1-22-10-13-5-7-16(23-2)21(24-3)19(13)14-6-4-12-8-17-18(26-11-25-17)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1

> <INCHI_KEY>
TZJGMJCNKZKQBJ-UHFFFAOYSA-N

> <FORMULA>
C21H18NO4

> <MOLECULAR_WEIGHT>
348.377

> <EXACT_MASS>
348.123034484

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
38.44365179267621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15,16-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18,20-nonaen-21-ium

> <ALOGPS_LOGP>
-0.25

> <JCHEM_LOGP>
-0.882072640805079

> <ALOGPS_LOGS>
-6.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.379010154465939

> <JCHEM_POLAR_SURFACE_AREA>
40.8

> <JCHEM_REFRACTIVITY>
97.9779

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.32e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15,16-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18,20-nonaen-21-ium

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -3.1114    0.5486   -6.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2158    1.0660   -6.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    0.2042   -5.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306   -1.1651   -5.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -1.9482   -4.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6619   -1.3778   -3.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -2.2036   -2.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -1.7556   -0.9448 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5869   -2.7072    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -0.4524   -0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954    0.0031    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -0.8212    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286   -0.2712    1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791    1.0725    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    1.9362    1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0422    1.4070    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    2.2959   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    1.8404   -1.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457    0.4737   -1.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160    0.0021   -2.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377    0.7697   -4.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    2.1261   -4.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    2.5116   -5.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    1.4102    2.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1006    0.1130    3.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.9642    2.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043   -0.1657   -7.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.3853   -7.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929    0.0996   -6.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048   -1.6554   -5.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878   -3.0215   -4.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -3.2677   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -3.3509    0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -2.1680    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4773   -3.3221    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824   -1.8864    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979    3.0063    1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    3.3732   -0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650    2.6202   -2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710    3.3355   -4.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    2.8833   -5.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7871    1.7019   -5.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197   -0.0608    4.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1811    0.1062    3.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  2  0
 20  6  1  0
  5  6  2  0
 16 11  1  0
  6  7  1  0
 11 12  1  0
 12 13  2  0
  3  4  2  0
 14 15  2  0
 15 16  1  0
 14 13  1  0
  7  8  2  0
  8 10  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 13 26  1  0
 26 25  1  0
 25 24  1  0
 24 14  1  0
 19 10  1  0
  3  2  1  0
 10 11  2  0
 21 22  1  0
 22 23  1  0
 16 17  2  0
  2  1  1  0
  4  5  1  0
  8  9  1  0
  4 30  1  0
  5 31  1  0
  7 32  1  0
 17 38  1  0
 18 39  1  0
 12 36  1  0
 15 37  1  0
 25 43  1  0
 25 44  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
M  CHG  1   8   1
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.111   0.549  -7.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.216   1.066  -6.023  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.718   0.204  -5.083  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.931  -1.165  -5.088  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.398  -1.948  -4.069  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.662  -1.378  -3.015  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.209  -2.204  -2.005  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.494  -1.756  -0.945  0.00  0.00           N+1
HETATM    9  C   UNK     0       0.587  -2.707   0.188  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.925  -0.452  -0.863  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.895   0.003   0.119  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.782  -0.821   0.873  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.629  -0.271   1.817  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.679   1.073   2.040  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.906   1.936   1.306  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.042   1.407   0.329  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.337   2.296  -0.465  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.548   1.840  -1.519  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.346   0.474  -1.797  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.416   0.002  -2.943  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.938   0.770  -4.047  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.693   2.126  -4.074  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.134   2.512  -5.176  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.576   1.410   2.999  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.101   0.113   3.354  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.496  -0.964   2.600  0.00  0.00           O+0
HETATM   27  H   UNK     0      -2.604  -0.166  -7.656  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.452   1.385  -7.617  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.993   0.100  -6.530  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.505  -1.655  -5.869  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.588  -3.022  -4.110  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.441  -3.268  -2.011  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.300  -3.351   0.185  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.578  -2.168   1.137  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.477  -3.322   0.043  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.882  -1.886   0.713  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.998   3.006   1.475  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.428   3.373  -0.317  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.065   2.620  -2.102  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.771   3.336  -4.840  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.484   2.883  -5.999  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.787   1.702  -5.522  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.920  -0.061   4.421  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.181   0.106   3.170  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    4   21    2                                                  
CONECT    4    3    5   30                                                  
CONECT    5    6    4   31                                                  
CONECT    6   20    5    7                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8   33   34   35                                             
CONECT   10    8   19   11                                                  
CONECT   11   16   12   10                                                  
CONECT   12   11   13   36                                                  
CONECT   13   12   14   26                                                  
CONECT   14   15   13   24                                                  
CONECT   15   14   16   37                                                  
CONECT   16   11   15   17                                                  
CONECT   17   18   16   38                                                  
CONECT   18   17   19   39                                                  
CONECT   19   18   20   10                                                  
CONECT   20    6   19   21                                                  
CONECT   21   20    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   40   41   42                                             
CONECT   24   25   14                                                       
CONECT   25   26   24   43   44                                             
CONECT   26   13   25                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    5                                                            
CONECT   32    7                                                            
CONECT   33    9                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   12                                                            
CONECT   37   15                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   23                                                            
CONECT   41   23                                                            
CONECT   42   23                                                            
CONECT   43   25                                                            
CONECT   44   25                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

RDKit          3D

44 48  0  0  0  0  0  0  0  0999 V2000
   -3.1114    0.5486   -6.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2158    1.0660   -6.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7179    0.2042   -5.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306   -1.1651   -5.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -1.9482   -4.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6619   -1.3778   -3.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2092   -2.2036   -2.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -1.7556   -0.9448 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.5869   -2.7072    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -0.4524   -0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954    0.0031    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -0.8212    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286   -0.2712    1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791    1.0725    2.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    1.9362    1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0422    1.4070    0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    2.2959   -0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483    1.8404   -1.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457    0.4737   -1.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4160    0.0021   -2.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9377    0.7697   -4.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    2.1261   -4.0736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1341    2.5116   -5.1763 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    1.4102    2.9990 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1006    0.1130    3.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4956   -0.9642    2.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6043   -0.1657   -7.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4517    1.3853   -7.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9929    0.0996   -6.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048   -1.6554   -5.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878   -3.0215   -4.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4410   -3.2677   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995   -3.3509    0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5783   -2.1680    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4773   -3.3221    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824   -1.8864    0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979    3.0063    1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    3.3732   -0.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0650    2.6202   -2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7710    3.3355   -4.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    2.8833   -5.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7871    1.7019   -5.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9197   -0.0608    4.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1811    0.1062    3.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
 18 19  2  0
 20  6  1  0
  5  6  2  0
 16 11  1  0
  6  7  1  0
 11 12  1  0
 12 13  2  0
  3  4  2  0
 14 15  2  0
 15 16  1  0
 14 13  1  0
  7  8  2  0
  8 10  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 13 26  1  0
 26 25  1  0
 25 24  1  0
 24 14  1  0
 19 10  1  0
  3  2  1  0
 10 11  2  0
 21 22  1  0
 22 23  1  0
 16 17  2  0
  2  1  1  0
  4  5  1  0
  8  9  1  0
  4 30  1  0
  5 31  1  0
  7 32  1  0
 17 38  1  0
 18 39  1  0
 12 36  1  0
 15 37  1  0
 25 43  1  0
 25 44  1  0
 23 40  1  0
 23 41  1  0
 23 42  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
M  CHG  1   8   1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈NO₄

Average Mass

348.3770 Da

Monoisotopic Mass

348.12303 Da

IUPAC Name

15,16-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18,20-nonaen-21-ium

Traditional Name

15,16-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1,3,8,10,12,14,16,18,20-nonaen-21-ium

CAS Registry Number

Not Available

SMILES

[H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2C(=C1[H])C([H])=[N+](C1=C3C([H])=C4OC([H])([H])OC4=C([H])C3=C([H])C([H])=C21)C([H])([H])[H]

InChI Identifier

InChI=1S/C21H18NO4/c1-22-10-13-5-7-16(23-2)21(24-3)19(13)14-6-4-12-8-17-18(26-11-25-17)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1

InChI Key

TZJGMJCNKZKQBJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

synthesis

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthridines and derivatives. These are polycyclic compounds containing a phenanthridine moiety, which is a tricyclic system with two benzene rings joined by a pyridine forming a non-linear skeleton. Hydrogenated derivatives are also included.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Phenanthridines and derivatives

Alternative Parents

Substituents

Phenanthridine
Isoquinoline
Naphthalene
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Pyridine
Pyridinium
Heteroaromatic compound
Acetal
Ether
Oxacycle
Azacycle
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen 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	-0.25	ALOGPS
logP	-0.88	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.98 m³·mol⁻¹	ChemAxon
Polarizability	38.44 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

28284090

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101497139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ishihara, Y., et al. (2011). Ishihara, Y., et al, Tetrahedron 67, 1320 (2011).. Tetrahedron.

Showing NP-Card for broussonpapyrine (NP0040212)

MOL for NP0040212 (broussonpapyrine)

3D MOL for NP0040212 (broussonpapyrine)

3D SDF for NP0040212 (broussonpapyrine)

3D-SDF for NP0040212 (broussonpapyrine)

PDB for NP0040212 (broussonpapyrine)

3D PDB for NP0040212 (broussonpapyrine)

SMILES for NP0040212 (broussonpapyrine)

INCHI for NP0040212 (broussonpapyrine)

Structure for NP0040212 (broussonpapyrine)

3D Structure for NP0040212 (broussonpapyrine)