NP-MRD: Showing NP-Card for methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate (NP0259171)

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Record Information

Version

2.0

Created at

2022-09-08 00:57:10 UTC

Updated at

2022-09-08 00:57:10 UTC

NP-MRD ID

NP0259171

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate

Description

Methyl (13E)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]Octadeca-2(7),3,5,8-tetraene-18-carboxylate belongs to the class of organic compounds known as akuammilan and related alkaloids. These are alkaloids with a structure based on either the akuammilan skeleton. The ring system in this group is formed from a precursor of the corynantheine type by bond formation between C-16 and C-7. Variations in this subgroup include, among others, alkaloids derived by C-3 to N-4 bond fission, as well as alkaloids in which the N-4 to C-5 bond in the Akuammiline skeleton has been severed. methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate is found in Alstonia angustifolia. Methyl (13E)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]Octadeca-2(7),3,5,8-tetraene-18-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201506302D          

 25 29  0  0  0  0            999 V2000
    3.7055    3.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9950    3.1532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088    3.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3331    3.6546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0983    2.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0256    2.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1707    1.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5861    0.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8421    0.2599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985   -0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854    0.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4856    1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8371    0.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2359    0.2252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128    0.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338    0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -0.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091    0.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635    1.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425    1.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6672    1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7018    0.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8340    1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5981    1.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7105    2.6196    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
  3  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 15 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
   -3.8158    0.7897   -1.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775   -0.5943   -1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124   -0.8645   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5105   -2.2314    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817   -2.4534    1.0258 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417   -2.8762    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176   -1.7551   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4102   -0.5359   -0.0678 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4652   -0.9276    1.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352   -0.7475    1.8582 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5104   -0.2387    0.8605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8509    0.0912    0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5712   -0.0448    2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4862    0.5747   -0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828    0.7137   -1.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4599    0.3723   -1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831   -0.1092   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605   -1.4216    1.9018 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7432   -0.1936    1.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9207    0.2262    0.4746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6340    0.5288   -0.2102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1556    1.8858    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8540    2.5587    0.9498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0103    2.4496   -0.3378 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3481    3.7532    0.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688    0.7699   -2.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477    1.5012   -0.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0045    1.1686   -2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1350   -1.4427   -1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4864   -2.8993   -0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3358   -2.6343    0.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -3.8066   -0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6896   -2.9936    0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9187   -2.0066   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8141   -1.5488   -1.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5365    0.2029    2.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5403    0.8242   -0.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3079    1.0891   -2.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8990    0.4790   -2.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7088   -1.8535    2.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347    0.5694    2.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603   -0.4400    2.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5038    1.1923    0.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8698    0.5848   -1.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972    3.8552    1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8143    4.4869   -0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4471    3.9517   -0.0093 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  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
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  8 21  1  0
 17  8  1  0
  3 20  1  0
  9 18  1  0
 17 11  1  0
 25 45  1  0
 25 46  1  0
 25 47  1  0
 21 44  1  6
 20 43  1  1
 19 41  1  0
 19 42  1  0
 18 40  1  1
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
  4 30  1  0
  4 31  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END


  Mrv1533004201506302D          

 25 29  0  0  0  0            999 V2000
    3.7055    3.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9950    3.1532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8088    3.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3331    3.6546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0983    2.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0256    2.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1707    1.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5861    0.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8421    0.2599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985   -0.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854    0.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4856    1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8371    0.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2359    0.2252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5128    0.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7338    0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -0.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091    0.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635    1.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425    1.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6672    1.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7018    0.5575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8340    1.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5981    1.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7105    2.6196    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
  3  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 15 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C2CC3N(CCC11C3=NC3=C(O)C=CC=C13)C\C2=C\C

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

> <INCHI_KEY>
HFAMTZLWVCDXLU-JYOAFUTRSA-N

> <FORMULA>
C20H22N2O3

> <MOLECULAR_WEIGHT>
338.407

> <EXACT_MASS>
338.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.99216294854239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (13E)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.391739731674975

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.193879853557545

> <JCHEM_PKA_STRONGEST_BASIC>
6.784380585316907

> <JCHEM_POLAR_SURFACE_AREA>
62.129999999999995

> <JCHEM_REFRACTIVITY>
97.2454

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (13E)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       6.917   7.328   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.457   5.886   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.976   5.633   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.955   6.822   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.517   4.191   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.248   3.945   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.519   2.992   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.427   1.761   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      10.905   0.485   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       9.331  -0.151   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.999   1.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.373   2.868   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.029   1.475   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.907   0.420   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.557   1.162   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.103   0.655   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.815  -0.858   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.937   1.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.225   3.174   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.679   3.681   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.845   2.675   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.510   1.041   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.757   2.783   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.183   3.364   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.393   4.890   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13   21                                             
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   15                                                  
CONECT   22    9   23                                                       
CONECT   23   22    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
Methyl (13E)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0,.0,.0,]octadeca-2(7),3,5,8-tetraene-18-carboxylic acid	Generator
Methyl (13E)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2(7),3,5,8-tetraene-18-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₂N₂O₃

Average Mass

338.4070 Da

Monoisotopic Mass

338.16304 Da

IUPAC Name

methyl (13E)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate

Traditional Name

methyl (13E)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1C2CC3N(CCC11C3=NC3=C(O)C=CC=C13)C\C2=C\C

InChI Identifier

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

InChI Key

HFAMTZLWVCDXLU-JYOAFUTRSA-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 angustifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as akuammilan and related alkaloids. These are alkaloids with a structure based on either the akuammilan skeleton. The ring system in this group is formed from a precursor of the corynantheine type by bond formation between C-16 and C-7. Variations in this subgroup include, among others, alkaloids derived by C-3 to N-4 bond fission, as well as alkaloids in which the N-4 to C-5 bond in the Akuammiline skeleton has been severed.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Akuammilan and related alkaloids

Sub Class

Not Available

Direct Parent

Akuammilan and related alkaloids

Alternative Parents

Substituents

Akuammilan skeleton
3-alkylindole
Quinolizidine
Indole or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Piperidine
Methyl ester
Tertiary aliphatic amine
Tertiary amine
Ketimine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Amine
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	2.89	ALOGPS
logP	2.39	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.19	ChemAxon
pKa (Strongest Basic)	6.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.25 m³·mol⁻¹	ChemAxon
Polarizability	35.99 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate (NP0259171)

MOL for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

3D MOL for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

3D SDF for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

3D-SDF for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

PDB for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

3D PDB for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

SMILES for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

INCHI for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

Structure for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)

3D Structure for NP0259171 (methyl (13e)-13-ethylidene-6-hydroxy-8,15-diazapentacyclo[10.5.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵]octadeca-2,4,6,8-tetraene-18-carboxylate)