NP-MRD: Showing NP-Card for Deacetyldeformopicraline (NP0067446)

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Record Information

Version

2.0

Created at

2022-04-28 12:18:07 UTC

Updated at

2022-04-28 12:18:07 UTC

NP-MRD ID

NP0067446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deacetyldeformopicraline

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. Deacetyldeformopicraline is found in Alstonia scholaris, Alstonia macrophylla, Alstonia scholaris R.Br. , Alstonia yunnanensis, Ervatamia officinalis , Rauvolfia bahiensis, Rauwolfia sellowii, Rauwolfia vomitoria and Vinca erecta Rgl.et Schmalh.. Deacetyldeformopicraline was first documented in 2020 (PMID: 32387234). Based on a literature review a small amount of articles have been published on Picrinine (PMID: 35176533) (PMID: 34325978) (PMID: 33148433) (PMID: 34410141).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214182D          

 25 30  0  0  1  0            999 V2000
    0.6969   -1.7586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2014   -0.9908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6679   -0.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2382   -1.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -0.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557    0.2713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115   -0.3642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3487   -0.4792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5739    0.2119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543    0.4398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1708   -0.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022    0.5843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3749   -0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712   -1.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -1.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2722   -2.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991   -1.7159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8768   -1.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3195   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -2.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7661   -3.1858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887   -3.9194    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  6  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  1  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  6  0  0  0
 11 21  1  0  0  0  0
  1 22  1  6  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
   -3.2478   -1.1462    1.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9475   -1.9079    0.7363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587   -1.3583   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720   -2.1601   -1.4486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489   -1.8632   -2.0806 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4301   -2.3874   -1.4779 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6548   -1.9570   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7455   -0.4573   -0.1930 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0533    0.0903    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7890   -0.0008    1.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0146    0.6181    1.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5420    1.3592    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8085    1.4521   -0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    0.8407   -0.8287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.7918   -1.9271 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8303   -0.3158   -1.6743 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4098   -1.5477   -2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5064   -0.4291   -2.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5450    0.4365   -1.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7248    0.0242   -0.2082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4064    0.1691    0.4883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2499    1.6106    0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558    2.3566    0.4131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2179    2.1722    1.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517    3.5590    2.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6494   -0.1452    1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0833   -1.6615    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4115   -1.1039    2.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2936   -2.9264    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0335   -3.2374   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8026   -1.9021   -2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6254   -3.4388   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0802   -2.3089    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6480   -2.3257    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3925   -0.5860    2.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5781    0.5284    2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5035    1.8443    0.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2255    2.0425   -1.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6395    1.4740   -2.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4872   -0.1899   -3.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799    1.4802   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808    0.3532   -2.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    0.6972    0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4698   -0.3284    1.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    4.1191    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294    3.9065    2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117    3.7596    2.6771 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  6
  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  1
 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  1
 20 43  1  1
 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


  Mrv1652304282214182D          

 25 30  0  0  1  0            999 V2000
    0.6969   -1.7586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2014   -0.9908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6679   -0.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2382   -1.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397   -1.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -0.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7005    0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1557    0.2713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6115   -0.3642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3487   -0.4792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5739    0.2119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543    0.4398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1708   -0.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0022    0.5843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3749   -0.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712   -1.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -1.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2722   -2.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991   -1.7159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8768   -1.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3195   -2.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -2.5321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7661   -3.1858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887   -3.9194    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  6  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  1  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  6  0  0  0
 11 21  1  0  0  0  0
  1 22  1  6  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>
NP0067446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1[C@H]2C[C@@H]3N(C\C2=C\C)[C@@H]2C[C@]11C4=CC=CC=C4N[C@]31O2

> <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-/t12-,15-,16-,17+,19-,20-/m0/s1

> <INCHI_KEY>
BDXYPHKGNUGUFG-UYIKASJQSA-N

> <FORMULA>
C20H22N2O3

> <MOLECULAR_WEIGHT>
338.407

> <EXACT_MASS>
338.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.48932743789218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,9R,11S,14E,15R,17S,19S)-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

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
2.352270998

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.633543406108256

> <JCHEM_PKA_STRONGEST_BASIC>
4.900722677992653

> <JCHEM_POLAR_SURFACE_AREA>
50.8

> <JCHEM_REFRACTIVITY>
94.29849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,9R,11S,14E,15R,17S,19S)-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                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.301  -3.283   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.376  -1.849   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.247  -1.793   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.311  -2.905   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.807  -2.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.239  -1.062   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.174   0.051   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.678  -0.314   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.291   0.506   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.141  -0.680   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.517  -0.895   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.938   0.396   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.848   0.821   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.319  -0.509   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.871   1.091   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.433  -0.392   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.613  -2.169   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.998  -2.842   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.108  -4.378   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.985  -3.203   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.503  -2.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.596  -4.652   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.942  -4.727   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.430  -5.947   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.726  -7.316   0.000  0.00  0.00           C+0
CONECT    1    2   20   22                                                  
CONECT    2    1    3   10   14                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    2   11   15                                             
CONECT   11   10   12   21                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    2                                                       
CONECT   15   13   10                                                       
CONECT   16   12   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    1   21                                                  
CONECT   21   20   11                                                       
CONECT   22    1   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 (1R,9R,11S,14E,15R,17S,19S)-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 (1R,9R,11S,14E,15R,17S,19S)-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)[C@H]1[C@H]2C[C@@H]3N(C\C2=C\C)[C@@H]2C[C@]11C4=CC=CC=C4N[C@]31O2

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-/t12-,15-,16-,17+,19-,20-/m0/s1

InChI Key

BDXYPHKGNUGUFG-UYIKASJQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 macrophylla	LOTUS Database	35616633
Alstonia scholaris R.Br.	Plant	KNApSAcK
Alstonia yunnanensis	Plant	KNApSAcK
Ervatamia officinalis	Plant	KNApSAcK
Rauvolfia bahiensis	Plant	KNApSAcK
Rauwolfia sellowii	Plant	KNApSAcK
Rauwolfia vomitoria	Plant	KNApSAcK
Vinca erecta Rgl.et Schmalh.	Plant	KNApSAcK

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
Secondary aliphatic/aromatic amine
Piperidine
Benzenoid
Oxazolidine
Methyl ester
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Hemiaminal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Secondary amine
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
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	2.69	ALOGPS
logP	2.35	ChemAxon
logS	-2.5	ALOGPS
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	35.49 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Picrinine

METLIN ID

Not Available

PubChem Compound

85473463

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 ]
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 ]

Showing NP-Card for Deacetyldeformopicraline (NP0067446)

MOL for NP0067446 (Deacetyldeformopicraline)

3D MOL for NP0067446 (Deacetyldeformopicraline)

3D SDF for NP0067446 (Deacetyldeformopicraline)

3D-SDF for NP0067446 (Deacetyldeformopicraline)

PDB for NP0067446 (Deacetyldeformopicraline)

3D PDB for NP0067446 (Deacetyldeformopicraline)

SMILES for NP0067446 (Deacetyldeformopicraline)

INCHI for NP0067446 (Deacetyldeformopicraline)

Structure for NP0067446 (Deacetyldeformopicraline)

3D Structure for NP0067446 (Deacetyldeformopicraline)