NP-MRD: Showing NP-Card for 4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium (NP0230259)

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Record Information

Version

2.0

Created at

2022-09-06 10:39:33 UTC

Updated at

2022-09-06 10:39:33 UTC

NP-MRD ID

NP0230259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium

Description

Dehydroantofine belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. 4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium was first documented in 2012 (PMID: 22816292). Based on a literature review a small amount of articles have been published on Dehydroantofine (PMID: 35249209) (PMID: 33482050).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062212392D          

 27 31  0  0  0  0            999 V2000
    0.7720   -6.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -5.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235   -5.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357   -5.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3675   -4.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433   -4.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -1.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -0.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    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  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  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
  6 24  1  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
M  CHG  1  22   1
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    2.8949    5.6081   -0.7721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0443    4.2827   -0.3087 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025    3.3916   -0.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8110    3.7693   -0.9842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2353    2.8862   -1.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    1.6010   -0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299    1.1922   -0.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525    2.1034    0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663   -0.1088    0.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532   -0.5309    0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6244   -1.8268    1.4066 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8021   -2.2513    1.9742 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9726   -1.5420    2.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789   -2.7100    1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7155   -4.0046    1.7344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -4.9315    1.6239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621   -2.3396    0.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2348   -1.0424    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9450   -0.6047   -0.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9874   -1.4945   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1711   -1.0457   -0.9941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995    0.1996   -1.4239 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.2987    1.1112   -1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    0.7012   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441    0.3997   -1.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4165   -0.8118   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4099   -1.8635   -1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9051    6.1033   -0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773    6.1865   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5046    5.6732   -1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024    4.8062   -1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348    3.2270   -1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1094    1.8728    0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2632    0.1771    1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1372   -1.4087    3.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9800   -0.5314    1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8392   -2.1510    1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2435   -4.5670    2.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629   -5.1074    0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9073   -5.9046    2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4089   -3.0944    0.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9266   -2.5228   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5276    2.0837   -1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0931    1.3435   -1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5904    0.4148   -3.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0731   -0.5831   -0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0961   -1.1832   -2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7192   -2.3412   -0.2362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2648   -2.6314   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 22 23  1  0
 23 24  2  0
  8  3  1  0
 18  9  1  0
 24 19  1  0
 24  6  1  0
 27 21  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  5 32  1  0
  8 33  1  0
 10 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
 27 48  1  0
 27 49  1  0
 23 43  1  0
M  CHG  1  22   1
M  END


  Mrv1652309062212392D          

 27 31  0  0  0  0            999 V2000
    0.7720   -6.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -5.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235   -5.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8357   -5.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3675   -4.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433   -4.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -1.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -0.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -2.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -2.6434    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.4311   -3.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -3.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -2.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -1.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -1.3611    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  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  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
  6 24  1  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
M  CHG  1  22   1
M  END
> <DATABASE_ID>
NP0230259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(=C1)C1=CC(OC)=C(OC)C=C1C1=CC3=[N+](CCC3)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C23H22NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,9-13H,4-5,8H2,1-3H3/q+1

> <INCHI_KEY>
SLUPUHLVPJEPNB-UHFFFAOYSA-N

> <FORMULA>
C23H22NO3

> <MOLECULAR_WEIGHT>
360.432

> <EXACT_MASS>
360.159419993

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
41.329907251602236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,10-trimethoxy-16lambda5-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(21),2,4,6,8,10,12,14,16(20)-nonaen-16-ylium

> <JCHEM_LOGP>
-0.7998545668050788

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-4.401592187986308

> <JCHEM_POLAR_SURFACE_AREA>
31.57

> <JCHEM_REFRACTIVITY>
106.53299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,5,10-trimethoxy-16lambda5-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(21),2,4,6,8,10,12,14,16(20)-nonaen-16-ylium

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.441 -11.998   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.918 -10.550   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.911  -9.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.427  -9.644   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.419  -8.466   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.896  -7.018   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.380  -6.747   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.387  -7.924   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.857  -5.298   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.341  -5.027   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.182  -3.579   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.698  -3.308   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.221  -1.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.810  -2.402   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.287  -0.953   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.229  -0.682   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.326  -2.673   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.850  -4.121   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.366  -4.392   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.358  -3.215   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.874  -3.486   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       7.398  -4.934   0.000  0.00  0.00           N+1
HETATM   23  C   UNK     0       6.405  -6.112   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.889  -5.841   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.937  -4.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.365  -3.405   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.090  -2.541   0.000  0.00  0.00           C+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   24                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17    9   19                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23    6   19                                                  
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂NO₃

Average Mass

360.4320 Da

Monoisotopic Mass

360.15942 Da

IUPAC Name

4,5,10-trimethoxy-16lambda5-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(21),2,4,6,8,10,12,14,16(20)-nonaen-16-ylium

Traditional Name

4,5,10-trimethoxy-16lambda5-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(21),2,4,6,8,10,12,14,16(20)-nonaen-16-ylium

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(=C1)C1=CC(OC)=C(OC)C=C1C1=CC3=[N+](CCC3)C=C21

InChI Identifier

InChI=1S/C23H22NO3/c1-25-15-6-7-16-18(10-15)20-12-23(27-3)22(26-2)11-19(20)17-9-14-5-4-8-24(14)13-21(16)17/h6-7,9-13H,4-5,8H2,1-3H3/q+1

InChI Key

SLUPUHLVPJEPNB-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Isoquinoline
Naphthalene
Anisole
Phenol ether
Alkyl aryl ether
Pyridinium
Pyridine
Heteroaromatic compound
Organoheterocyclic compound
Ether
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen 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	-0.8	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	31.57 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.53 m³·mol⁻¹	ChemAxon
Polarizability	41.33 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25043077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14489153

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matsuo H, Kawakami H, Anjiki N, Kawano N, Fuchino H, Kawahara N, Yoshimatsu K: Phenanthroindolizine alkaloids from Boehmeria sieboldiana leaves exhibit cytotoxicity against human cancer cell lines. J Nat Med. 2022 Jun;76(3):670-674. doi: 10.1007/s11418-022-01610-9. Epub 2022 Mar 6. [PubMed:35249209 ]
Yamasaki N, Iwasaki I, Sakumi K, Hokari R, Ishiyama A, Iwatsuki M, Nakahara M, Higashibayashi S, Sugai T, Imagawa H, Kubo M, Fukuyama Y, Omura S, Yamamoto H: A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum. Chemistry. 2021 Mar 22;27(17):5555-5563. doi: 10.1002/chem.202100032. Epub 2021 Feb 26. [PubMed:33482050 ]
Wu TS, Sun CR, Lee KH: Cytotoxic and anti-HIV phenanthroindolizidine alkaloids from Cryptocarya chinensis. Nat Prod Commun. 2012 Jun;7(6):725-7. [PubMed:22816292 ]
LOTUS database [Link]

Showing NP-Card for 4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium (NP0230259)

MOL for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

3D MOL for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

3D SDF for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

3D-SDF for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

PDB for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

3D PDB for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

SMILES for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

INCHI for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

Structure for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)

3D Structure for NP0230259 (4,5,10-trimethoxy-16λ⁵-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11,15,20-nonaen-16-ylium)