NP-MRD: Showing NP-Card for 1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone (NP0187653)

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Record Information

Version

2.0

Created at

2022-09-04 03:52:03 UTC

Updated at

2022-09-04 03:52:03 UTC

NP-MRD ID

NP0187653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone

Description

Isoretuline, also known as 16-epiretuline, belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. 1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone was first documented in 2001 (PMID: 11509972). Based on a literature review very few articles have been published on isoretuline.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205522D          

 25 29  0  0  1  0            999 V2000
   -0.6354    0.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172    1.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4968    2.1185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    2.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886    2.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951    1.2328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5673    1.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000    2.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2166    1.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839    0.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592    0.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3741   -0.0084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5171   -0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849   -1.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922   -1.1033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153    0.3472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8118   -0.0676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8091   -0.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0934   -1.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081    0.3538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4045    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108    1.4408    0.0000 C   0  0  2  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
  8  7  1  6  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
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 19 15  1  1  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  6  0  0  0
  5 25  1  0  0  0  0
  8 25  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.5346    2.1331   -1.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4183    1.3336   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6483    0.2308   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6597   -0.4409    1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9771   -1.6567    1.4240 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1368   -1.6809    2.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543   -0.6799    2.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0519   -0.8921    0.7521 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4248   -1.3321    0.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0561   -2.5701    0.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3741   -2.7186    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1287   -1.6213   -0.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5284   -0.3850   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836   -0.2316    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3798    0.9317    0.1902 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7812    2.2520    0.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1741    2.6839    0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8833    3.1632    0.4439 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0037    0.4544    0.0849 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4616    0.2484   -1.3167 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2398    1.3963   -2.2460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    1.7464   -2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759   -0.2467   -1.2106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6874   -1.7510   -0.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -1.8505    0.3723 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5952    2.5307   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9196    3.0548   -1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4042    1.6249   -2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9609    1.6221    0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7660   -0.6004    1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3217    0.2504    2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6834   -1.3896    3.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6589   -2.6713    2.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8783   -0.9534    2.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3277    0.3541    2.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4265   -3.4200    0.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032   -3.7043    0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1831   -1.7093   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    0.4840   -0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6506    2.8026   -0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2072    3.6946    0.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7535    2.0249    1.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975    1.1341    0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2260   -0.5654   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    2.3291   -1.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4929    1.1619   -3.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6134    0.9064   -2.5505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4311   -0.1331   -2.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0576   -2.1908   -1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6518   -2.2575   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5851   -2.8958    0.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8 25  1  0
 25 24  1  0
 24 23  1  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 20 19  1  0
 19 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
 23  3  1  0
  9 14  1  0
 25  5  1  0
 19  8  1  0
  9  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
 25 51  1  1
 24 49  1  0
 24 50  1  0
 23 48  1  6
 20 44  1  6
 21 45  1  0
 21 46  1  0
 22 47  1  0
 19 43  1  1
 17 40  1  0
 17 41  1  0
 17 42  1  0
 13 39  1  0
 12 38  1  0
 11 37  1  0
 10 36  1  0
M  END


  Mrv1652309042205522D          

 25 29  0  0  1  0            999 V2000
   -0.6354    0.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881    0.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172    1.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.9016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4968    2.1185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    2.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8886    2.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6951    1.2328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5673    1.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0000    2.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2166    1.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839    0.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592    0.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3741   -0.0084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5171   -0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8849   -1.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922   -1.1033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153    0.3472    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8118   -0.0676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8091   -0.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0934   -1.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081    0.3538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4045    0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108    1.4408    0.0000 C   0  0  2  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
  8  7  1  6  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
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 19 15  1  1  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  6  0  0  0
  5 25  1  0  0  0  0
  8 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@@H](CO)[C@@H]3N(C(C)=O)C1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O2/c1-3-14-11-22-9-8-21-17-6-4-5-7-18(17)23(13(2)25)20(21)16(12-24)15(14)10-19(21)22/h3-7,15-16,19-20,24H,8-12H2,1-2H3/b14-3-/t15-,16+,19-,20-,21+/m0/s1

> <INCHI_KEY>
IJTKEUDLEABZCZ-YVBRLKKJSA-N

> <FORMULA>
C21H26N2O2

> <MOLECULAR_WEIGHT>
338.451

> <EXACT_MASS>
338.199428085

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.78161389975307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1R,9S,10R,11R,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6-trien-8-yl]ethan-1-one

> <JCHEM_LOGP>
1.0474800909999984

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.399784540623791

> <JCHEM_PKA_STRONGEST_BASIC>
9.23855027037353

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
98.43260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1R,9S,10R,11R,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6-trien-8-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.186   0.146   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.724   1.615   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.779   1.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220   3.550   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.794   3.955   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.116   4.878   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.392   3.936   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.031   2.301   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.659   2.434   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.467   3.745   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.006   3.702   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.738   2.346   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.930   1.035   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.391   1.079   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       6.298  -0.016   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.565  -1.532   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.385  -2.522   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.012  -2.060   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.882   0.648   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.382  -0.126   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.377  -1.666   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.041  -2.432   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.882   0.660   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.622   1.539   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.567   2.689   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19   25                                             
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   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   15    8   20                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
(19E)-1-Acetyl-19,20-didehydro-curan-17-ol	ChEBI
16-Epiretuline	ChEBI
16-Isoretuline	ChEBI

Chemical Formula

C₂₁H₂₆N₂O₂

Average Mass

338.4510 Da

Monoisotopic Mass

338.19943 Da

IUPAC Name

1-[(1R,9S,10R,11R,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6-trien-8-yl]ethan-1-one

Traditional Name

1-[(1R,9S,10R,11R,12E,17S)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6-trien-8-yl]ethanone

CAS Registry Number

Not Available

SMILES

C\C=C1\CN2CC[C@@]34[C@@H]2C[C@@H]1[C@@H](CO)[C@@H]3N(C(C)=O)C1=CC=CC=C41

InChI Identifier

InChI=1S/C21H26N2O2/c1-3-14-11-22-9-8-21-17-6-4-5-7-18(17)23(13(2)25)20(21)16(12-24)15(14)10-19(21)22/h3-7,15-16,19-20,24H,8-12H2,1-2H3/b14-3-/t15-,16+,19-,20-,21+/m0/s1

InChI Key

IJTKEUDLEABZCZ-YVBRLKKJSA-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 strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Akuammicine-skeleton
Stemmadenine-skeleton
Carbazole
Indole or derivatives
Indolizidine
Aralkylamine
Piperidine
N-alkylpyrrolidine
Benzenoid
Tertiary carboxylic acid amide
Acetamide
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Amine
Primary alcohol
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	1.05	ChemAxon
pKa (Strongest Acidic)	15.4	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.78 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.43 m³·mol⁻¹	ChemAxon
Polarizability	37.78 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

C00028651

Chemspider ID

10207546

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14880747

PDB ID

Not Available

ChEBI ID

141914

Good Scents ID

Not Available

References

General References

Frederich M, Hayette MP, Tits M, De Mol P, Angenot L: Reversal of chloroquine and mefloquine resistance in Plasmodium falciparum by the two monoindole alkaloids, icajine and isoretuline. Planta Med. 2001 Aug;67(6):523-7. doi: 10.1055/s-2001-16476. [PubMed:11509972 ]
LOTUS database [Link]

Showing NP-Card for 1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone (NP0187653)

MOL for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

3D MOL for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

3D SDF for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

3D-SDF for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

PDB for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

3D PDB for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

SMILES for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

INCHI for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

Structure for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)

3D Structure for NP0187653 (1-[(1r,9s,10r,11r,12e,17s)-12-ethylidene-10-(hydroxymethyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6-trien-8-yl]ethanone)