NP-MRD: Showing NP-Card for methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate (NP0285671)

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Record Information

Version

2.0

Created at

2022-09-09 13:56:26 UTC

Updated at

2022-09-09 13:56:26 UTC

NP-MRD ID

NP0285671

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

Description

Picrinine belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate is found in Alstonia scholaris, Alstonia angustiloba, Alstonia macrophylla, Alstonia yunnanensis, Amsonia tomentosa, Rauvolfia bahiensis, Rauvolfia sellowii, Rauvolfia volkensii, Tonduzia longifolia and Vinca minor. methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate was first documented in 2017 (PMID: 30192480). Based on a literature review a significant number of articles have been published on Picrinine (PMID: 35176533) (PMID: 34325978) (PMID: 33148433) (PMID: 32387234) (PMID: 31055046) (PMID: 35888731).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092215562D          

 25 30  0  0  0  0            999 V2000
   -1.6886    2.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    2.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598    1.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2981    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714    0.5654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055    0.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2468    0.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456    1.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9031    1.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487    2.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2574    2.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5206    1.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750    0.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663    0.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    0.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7288    1.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169    0.1337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9396    1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    2.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644    3.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6884    3.2286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4173    3.8814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    4.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 47 52  0  0  0  0  0  0  0  0999 V2000
   -4.1089    0.3614    1.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0692    0.7689    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856   -0.0957   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4470   -1.5302   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3156   -2.3367   -0.3263 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3356   -2.3816    0.7399 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0885   -0.9842    1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532   -0.4588   -0.0252 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2138   -0.2555    0.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9936    0.4127    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3824    0.4549    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.1704   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2401   -0.8364   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8609   -0.8873   -0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352   -1.5123   -1.7754 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7369   -1.6737   -0.9332 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8337   -2.7189    0.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -1.9747   -1.5248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1505   -0.8331   -2.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2814    0.3271   -1.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0571    0.6628   -0.6974 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1110    1.8698    0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    1.8897    1.3952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5120    3.0927   -0.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6760    4.2521    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8175    1.1867    1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005   -0.4976    0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6392    0.0007    2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    1.8376    0.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5930   -1.5766    1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594   -1.9798   -0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -3.0600    1.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7474   -0.3945    1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996   -1.1548    2.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5964    0.9368    1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857    0.9962    1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1005   -0.1469   -0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7544   -1.3354   -1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9771   -1.7563   -2.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4639   -2.8295   -2.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1559   -1.0314   -2.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -0.5371   -3.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5835    1.2089   -1.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7047    0.9878   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5263    4.8459    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2346    4.8613    0.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8297    3.9953    1.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 16 15  1  6
 16 17  1  0
  8 21  1  0
 16  8  1  0
  3 20  1  0
 17  6  1  0
 16 18  1  0
 14  9  1  0
 25 45  1  0
 25 46  1  0
 25 47  1  0
 21 44  1  6
 20 43  1  6
 19 41  1  0
 19 42  1  0
 18 40  1  6
  4 30  1  0
  4 31  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 32  1  1
  7 33  1  0
  7 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
M  END


  Mrv1652309092215562D          

 25 30  0  0  0  0            999 V2000
   -1.6886    2.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9672    2.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598    1.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2981    1.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714    0.5654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055    0.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2468    0.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0456    1.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9031    1.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487    2.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2574    2.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5206    1.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750    0.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1663    0.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194    0.4122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7288    1.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169    0.1337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9396    1.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    2.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8644    3.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6884    3.2286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4173    3.8814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    4.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C2CC3N(C\C2=C/C)C2CC11C4=CC=CC=C4NC31O2

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O3/c1-3-11-10-22-15-8-12(11)17(18(23)24-2)19-9-16(22)25-20(15,19)21-14-7-5-4-6-13(14)19/h3-7,12,15-17,21H,8-10H2,1-2H3/b11-3+

> <INCHI_KEY>
BDXYPHKGNUGUFG-QDEBKDIKSA-N

> <FORMULA>
C20H22N2O3

> <MOLECULAR_WEIGHT>
338.407

> <EXACT_MASS>
338.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.6952928957998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (14Z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3,5,7-triene-19-carboxylate

> <JCHEM_LOGP>
2.352270998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.633543406108258

> <JCHEM_PKA_STRONGEST_BASIC>
4.900722677992653

> <JCHEM_POLAR_SURFACE_AREA>
50.8

> <JCHEM_REFRACTIVITY>
94.29850000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (14Z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3,5,7-triene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.152   3.738   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.805   4.485   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.485   3.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.557   1.981   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.880   1.055   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.437   0.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.194   1.551   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.818   3.128   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.419   3.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.438   4.286   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.947   3.982   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.438   2.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.420   1.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.910   1.671   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.703   0.769   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.227   1.995   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.578   0.249   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.754   2.094   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.281   3.555   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.028   4.581   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.777   4.581   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.480   5.951   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.018   6.027   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.646   7.245   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.349   8.615   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16   21                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    8   17   18                                             
CONECT   17   16    6                                                       
CONECT   18   16    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20    8   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₃

Average Mass

338.4070 Da

Monoisotopic Mass

338.16304 Da

IUPAC Name

methyl (14Z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3,5,7-triene-19-carboxylate

Traditional Name

methyl (14Z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1^{9,15}.0^{1,9}.0^{3,8}.0^{12,17}]nonadeca-3,5,7-triene-19-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1C2CC3N(C\C2=C/C)C2CC11C4=CC=CC=C4NC31O2

InChI Identifier

InChI=1S/C20H22N2O3/c1-3-11-10-22-15-8-12(11)17(18(23)24-2)19-9-16(22)25-20(15,19)21-14-7-5-4-6-13(14)19/h3-7,12,15-17,21H,8-10H2,1-2H3/b11-3+

InChI Key

BDXYPHKGNUGUFG-QDEBKDIKSA-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
Alstonia Alstonia scholaris	LOTUS Database	35616633
Alstonia angustiloba	LOTUS Database	35616633
Alstonia macrophylla	LOTUS Database	35616633
Alstonia yunnanensis	LOTUS Database	35616633
Amsonia tomentosa	LOTUS Database	35616633
Rauvolfia bahiensis	LOTUS Database	35616633
Rauvolfia sellowii	LOTUS Database	35616633
Rauvolfia volkensii	LOTUS Database	35616633
Tonduzia longifolia	LOTUS Database	35616633
Vinca minor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Carbazole
Quinolizidine
Dihydroindole
Piperidine
Benzenoid
Oxazolidine
Oxolane
Methyl ester
Carboxylic acid ester
Hemiaminal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Amine
Carbonyl group
Organic oxygen compound
Organic nitrogen 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	2.35	ChemAxon
pKa (Strongest Acidic)	11.63	ChemAxon
pKa (Strongest Basic)	4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.3 m³·mol⁻¹	ChemAxon
Polarizability	35.7 Å³	ChemAxon
Number of Rings	6	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

C00025196

Chemspider ID

4586032

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Picrinine

METLIN ID

Not Available

PubChem Compound

5478940

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li R, Zhao YL, Qin F, Zhao Y, Xiao XR, Cao WY, Fan MR, Wang SG, Wu Y, Wang B, Fan CZ, Guo ZN, Yang QN, Zhang WT, Li XG, Li F, Luo XD, Gao R: The clinical population pharmacokinetics, metabolomics and therapeutic analysis of alkaloids from Alstonia scholaris leaves in acute bronchitis patients. Phytomedicine. 2022 Feb 5;98:153979. doi: 10.1016/j.phymed.2022.153979. [PubMed:35176533 ]
Mitra S, Prova SR, Sultana SA, Das R, Nainu F, Emran TB, Tareq AM, Uddin MS, Alqahtani AM, Dhama K, Simal-Gandara J: Therapeutic potential of indole alkaloids in respiratory diseases: A comprehensive review. Phytomedicine. 2021 Sep;90:153649. doi: 10.1016/j.phymed.2021.153649. Epub 2021 Jul 15. [PubMed:34325978 ]
Zhao YL, Pu SB, Qi Y, Wu BF, Shang JH, Liu YP, Hu D, Luo XD: Pharmacological effects of indole alkaloids from Alstonia scholaris (L.) R. Br. on pulmonary fibrosis in vivo. J Ethnopharmacol. 2021 Mar 1;267:113506. doi: 10.1016/j.jep.2020.113506. Epub 2020 Oct 22. [PubMed:33148433 ]
Zhao YL, Yang ZF, Wu BF, Shang JH, Liu YP, Wang XH, Luo XD: Indole alkaloids from leaves of Alstonia scholaris (L.) R. Br. protect against emphysema in mice. J Ethnopharmacol. 2020 Sep 15;259:112949. doi: 10.1016/j.jep.2020.112949. Epub 2020 May 5. [PubMed:32387234 ]
Li R, Zi MJ, Gou ZP, Zhao YL, Zhang WT, Lu F, Cao WY, Zhao YP, Li QN, Zhao Y, Wang SG, Gao HY, Sun MY, Luo XD, Xiong ZL, Gao R: Pharmacokinetics and safety evaluation in healthy Chinese volunteers of alkaloids from leaf of Alstonia scholaris: A multiple doses phase I clinical trial. Phytomedicine. 2019 Aug;61:152828. doi: 10.1016/j.phymed.2019.152828. Epub 2019 Jan 10. [PubMed:31055046 ]
Mahar R, Manivel N, Kanojiya S, Mishra DK, Shukla SK: Assessment of Tissue Specific Distribution and Seasonal Variation of Alkaloids in Alstonia scholaris. Metabolites. 2022 Jun 30;12(7):607. doi: 10.3390/metabo12070607. [PubMed:35888731 ]
Zou P, Yang H, Wei J, Wang T, Zhai H: Total Synthesis of (-)-Picrinine, (-)-Scholarisine C, and (+)-5-beta-Methoxyaspidophylline. Org Lett. 2021 Sep 3;23(17):6836-6840. doi: 10.1021/acs.orglett.1c02393. Epub 2021 Aug 19. [PubMed:34410141 ]
Zhao YL, Yang ZF, Shang JH, Huang WY, Wang B, Wei X, Khan A, Yuan ZW, Liu YP, Wang YF, Wang XH, Luo XD: Effects of indole alkaloids from leaf of Alstonia scholaris on post-infectious cough in mice. J Ethnopharmacol. 2018 May 23;218:69-75. doi: 10.1016/j.jep.2018.02.040. Epub 2018 Feb 26. [PubMed:29496577 ]
Yang NN, Yang CY, Wang YZ, Zhao YH: [Application of FTIR and Active Ingredients Quantitative Analysis on Quality Control of Dai Medicine Alstonia scholaris (L.) R. Br.]. Guang Pu Xue Yu Guang Pu Fen Xi. 2017 Jan;37(1):58-64. [PubMed:30192480 ]
LOTUS database [Link]

Showing NP-Card for methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate (NP0285671)

MOL for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D MOL for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D SDF for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D-SDF for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

PDB for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D PDB for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

SMILES for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

INCHI for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

Structure for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D Structure for NP0285671 (methyl (14z)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)