NP-MRD: Showing NP-Card for methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate (NP0195423)

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Record Information

Version

2.0

Created at

2022-09-04 13:16:55 UTC

Updated at

2022-09-04 13:16:55 UTC

NP-MRD ID

NP0195423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

Description

Conopharyngine belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond. methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate is found in Tabernaemontana africana, Tabernaemontana crassa, Tabernaemontana hystrix and Tabernaemontana pachysiphon. methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate was first documented in 2020 (PMID: 32232967). Based on a literature review very few articles have been published on Conopharyngine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215162D          

 29 33  0  0  1  0            999 V2000
    1.2601   -1.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345   -0.2099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0280    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    1.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777    1.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    1.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961    1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    1.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4277   -0.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191    0.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091    0.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3035    0.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8935    0.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3047    1.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8947    1.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6902    2.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103    1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203    1.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9372    0.1895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8834   -0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.9988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -1.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5158   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1031    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 10 22  1  0  0  0  0
 13 22  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
  5 28  1  0  0  0  0
 23 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29  7  1  6  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
   -3.8440   -2.1135   -1.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2228   -1.4125   -0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239   -0.0570   -0.0862 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9433    0.5785    1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271    0.5447    2.2536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3265   -0.8975    2.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347   -1.3454    1.1189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7793   -2.1739    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4723   -1.5033    1.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681   -0.3726    0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481    0.6704    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9670    1.4124   -0.5933 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118    0.9299   -0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4144    1.2964   -1.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545    0.5760   -0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7815    0.8780   -1.5293 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0520    1.9602   -2.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4728   -0.5593   -0.1661 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207   -1.3068    0.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5456   -2.4487    0.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2983   -0.9418    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680   -0.1934    0.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095    0.9170    0.3735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7721    2.0050   -0.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2713    3.0840   -0.1061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6709    1.8772   -1.9164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1161    2.9242   -2.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6154    1.3401    1.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0292   -0.3775    0.0741 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7391   -2.4401   -2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744   -1.4315   -2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -3.0167   -1.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9126   -2.0508    0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030   -1.2413   -0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7099    0.5568   -0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2617    1.6297    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    0.0383    1.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    0.9141    3.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0995   -1.5424    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5002   -0.8343    3.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9631   -3.0470    1.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6044   -2.5248    0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2878   -2.2820    1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4381   -1.1991    2.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787    2.2661   -1.1130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522    2.1765   -1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1177    2.2697   -2.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3461    2.8027   -2.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0645    1.5829   -3.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2308   -2.1801    1.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5579   -2.9005    0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8619   -3.2202    0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2246   -1.8323    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    2.5594   -3.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5686    3.8756   -2.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864    3.1171   -2.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7888    1.0663    2.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814    2.4116    1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6152   -0.8141   -0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  2  0
 11 23  1  0
 23 28  1  0
 23 29  1  0
 23 24  1  6
 24 25  2  0
 24 26  1  0
 26 27  1  0
 29  3  1  0
 28  5  1  0
 29  7  1  0
 22 10  1  0
 22 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  6
  4 36  1  0
  4 37  1  0
  5 38  1  1
  6 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 12 45  1  0
 14 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 28 57  1  0
 28 58  1  0
 29 59  1  6
 27 54  1  0
 27 55  1  0
 27 56  1  0
M  END


  Mrv1652309042215162D          

 29 33  0  0  1  0            999 V2000
    1.2601   -1.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345   -0.2099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0280    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    1.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777    1.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    1.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961    1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    1.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4277   -0.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191    0.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091    0.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3035    0.3735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8935    0.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3047    1.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8947    1.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6902    2.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103    1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203    1.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9372    0.1895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8834   -0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.9988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -1.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5158   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1031    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 10 22  1  0  0  0  0
 13 22  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
  5 28  1  0  0  0  0
 23 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29  7  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0195423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CC2CN3CCC4=C(NC5=CC(OC)=C(OC)C=C45)[C@](C2)([C@H]13)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O4/c1-5-14-8-13-11-23(22(26)29-4)20-15(6-7-25(12-13)21(14)23)16-9-18(27-2)19(28-3)10-17(16)24-20/h9-10,13-14,21,24H,5-8,11-12H2,1-4H3/t13?,14-,21-,23+/m0/s1

> <INCHI_KEY>
DUFLXLVGASPEMV-COUHDALUSA-N

> <FORMULA>
C23H30N2O4

> <MOLECULAR_WEIGHT>
398.503

> <EXACT_MASS>
398.220557454

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.94187070036407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

> <JCHEM_LOGP>
3.203526162666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.61431934962633

> <JCHEM_PKA_STRONGEST_BASIC>
8.412689909112386

> <JCHEM_POLAR_SURFACE_AREA>
63.790000000000006

> <JCHEM_REFRACTIVITY>
110.86489999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

> <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       2.352  -2.690   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.012  -1.932   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.998  -0.392   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.052   0.762   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.062   1.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.892   3.441   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.240   2.649   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.539   3.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.105   3.474   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.781   2.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.213   0.611   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.398  -0.372   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       7.699   0.452   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.182   0.036   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.284   1.113   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.767   0.697   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.868   1.774   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.902   2.605   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.003   3.681   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.622   5.173   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.419   3.020   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.318   1.944   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.616   0.354   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.516  -1.183   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.135  -1.864   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.796  -2.038   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.696  -3.575   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.770   1.639   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.059   0.818   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21   10   13                                                  
CONECT   23   11   24   28   29                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   23    5                                                       
CONECT   29   23    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀N₂O₄

Average Mass

398.5030 Da

Monoisotopic Mass

398.22056 Da

IUPAC Name

methyl (1S,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

Traditional Name

methyl (1S,17S,18S)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@H]1CC2CN3CCC4=C(NC5=CC(OC)=C(OC)C=C45)[C@](C2)([C@H]13)C(=O)OC

InChI Identifier

InChI=1S/C23H30N2O4/c1-5-14-8-13-11-23(22(26)29-4)20-15(6-7-25(12-13)21(14)23)16-9-18(27-2)19(28-3)10-17(16)24-20/h9-10,13-14,21,24H,5-8,11-12H2,1-4H3/t13?,14-,21-,23+/m0/s1

InChI Key

DUFLXLVGASPEMV-COUHDALUSA-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
Tabernaemontana africana	LOTUS Database	35616633
Tabernaemontana crassa	LOTUS Database	35616633
Tabernaemontana hystrix	LOTUS Database	35616633
Tabernaemontana pachysiphon	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ibogan-type alkaloids

Sub Class

Not Available

Direct Parent

Ibogan-type alkaloids

Alternative Parents

Substituents

Ibogan skeleton
Catharanthine skeleton
Pyrroloazepine
3-alkylindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
Anisole
Alkyl aryl ether
Azepine
Aralkylamine
Piperidine
Benzenoid
Methyl ester
Pyrrole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Ether
Amine
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen 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	3.2	ChemAxon
pKa (Strongest Acidic)	16.61	ChemAxon
pKa (Strongest Basic)	8.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.86 m³·mol⁻¹	ChemAxon
Polarizability	44.94 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

C00025731

Chemspider ID

59015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Conopharyngine

METLIN ID

Not Available

PubChem Compound

65572

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Krengel F, Dickinson J, Jenks C, Reyes-Chilpa R: Quantitative Evaluation of a Mexican and a Ghanaian Tabernaemontana Species as Alternatives to Voacanga africana for the Production of Antiaddictive Ibogan Type Alkaloids. Chem Biodivers. 2020 May;17(5):e2000002. doi: 10.1002/cbdv.202000002. Epub 2020 Apr 29. [PubMed:32232967 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate (NP0195423)

MOL for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D MOL for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D SDF for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D-SDF for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

PDB for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D PDB for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

SMILES for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

INCHI for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

Structure for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D Structure for NP0195423 (methyl (1s,17s,18s)-17-ethyl-6,7-dimethoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)