NP-MRD: Showing NP-Card for methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate (NP0277598)

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Record Information

Version

2.0

Created at

2022-09-09 02:19:46 UTC

Updated at

2022-09-09 02:19:46 UTC

NP-MRD ID

NP0277598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

Description

Eglandulosine 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,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-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 cymosa and Tabernaemontana peduncularis. Based on a literature review very few articles have been published on Eglandulosine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092204192D          

 27 31  0  0  1  0            999 V2000
    1.2742   -1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -1.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409   -0.2106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0255    0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5679    1.0124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4836    0.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9411    0.1976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8812   -0.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386   -0.9848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -1.0885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039   -1.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241   -0.2074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1184    0.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141    0.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5005    0.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090    1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853    1.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7281    1.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    2.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889    1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962    1.4226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714    1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0187    2.5322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1055    0.4412    0.0000 C   0  0  1  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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 24  1  6  0  0  0
  3 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -4.7750   -1.0795   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -1.2633   -0.4342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639   -0.0090   -0.0123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7438    0.1212    1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888   -0.1780    2.1366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4661    0.9080    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2153    0.8790    0.1659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3779    2.1963   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6132    2.7279   -1.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5531    2.9039   -0.5102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6977    4.1723   -1.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2140    0.4070   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756    1.1917    0.4905 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3940    0.6499    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6828    1.0716    0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7412    0.2877    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -0.8834   -0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2317   -1.2822   -0.7960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1518   -0.5238   -0.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747   -0.6811   -0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -1.7899   -1.2954 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9160   -2.7344   -1.8692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472   -2.4736   -0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369   -1.4151    0.2028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9866   -1.4888    1.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9787   -2.5127    2.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1377   -0.1856   -0.4396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4413   -1.6045   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0590   -0.0109    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9755   -1.5782    0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519   -1.4386   -1.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9481   -2.1511    0.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0597    0.8329   -0.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    1.1594    1.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4500   -0.6290    1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756   -0.2043    3.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4808    0.9392    2.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809    1.8962    1.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639    4.4455   -1.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    4.8920   -0.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3630    4.1458   -2.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    2.1056    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8232    1.9834    1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7836    0.5584    0.4257 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3403   -1.5316   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0498   -2.2011   -1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788   -1.3701   -2.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887   -2.8544   -2.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7504   -2.9827    0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4598   -3.2066   -0.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0578   -0.2115   -1.5300 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 27  1  0
 27 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 24 25  1  0
 25 26  2  0
  7  8  1  6
  8  9  2  0
  8 10  1  0
 10 11  1  0
 27  3  1  0
 19 20  1  0
 25  5  1  0
 12  7  1  0
 19 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  6
  4 34  1  0
  4 35  1  0
  5 36  1  1
  6 37  1  0
  6 38  1  0
 27 51  1  6
 23 49  1  0
 23 50  1  0
 21 47  1  6
 22 48  1  0
 13 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
M  END


  Mrv1652309092204192D          

 27 31  0  0  1  0            999 V2000
    1.2742   -1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -1.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409   -0.2106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0255    0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5679    1.0124    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4836    0.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9411    0.1976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8812   -0.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386   -0.9848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638   -1.0885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039   -1.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857    0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241   -0.2074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1184    0.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141    0.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5005    0.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911    1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090    1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0853    1.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7281    1.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    2.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889    1.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1962    1.4226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714    1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0187    2.5322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1055    0.4412    0.0000 C   0  0  1  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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 24  1  6  0  0  0
  3 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0277598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(CC(O)C1=C3NC3=CC=CC=C13)C2=O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O4/c1-3-11-8-12-9-21(20(26)27-2)17-16(13-6-4-5-7-14(13)22-17)15(24)10-23(18(11)21)19(12)25/h4-7,11-12,15,18,22,24H,3,8-10H2,1-2H3/t11-,12+,15?,18-,21+/m0/s1

> <INCHI_KEY>
WPAFASNFOAYXNJ-KFPATTCQSA-N

> <FORMULA>
C21H24N2O4

> <MOLECULAR_WEIGHT>
368.433

> <EXACT_MASS>
368.173607261

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.43253871357519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,15R,17S,18S)-17-ethyl-11-hydroxy-14-oxo-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>
1.8259858340000008

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.410790141247848

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.070687031598364

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5894669357096362

> <JCHEM_POLAR_SURFACE_AREA>
82.63

> <JCHEM_REFRACTIVITY>
98.87439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,15R,17S,18S)-17-ethyl-11-hydroxy-14-oxo-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                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       2.378  -2.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.033  -1.933   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.010  -0.393   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.048   0.754   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   1.890   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.769   1.648   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.623   0.369   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.512  -1.167   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.125  -1.838   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.786  -2.032   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.674  -3.568   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.200   0.588   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.392  -0.387   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       7.688   0.445   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.173   0.039   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.268   1.122   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.877   2.612   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.391   3.018   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.297   1.935   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.759   2.023   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.092   3.498   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.002   4.741   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.526   3.683   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       2.233   2.656   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       0.880   3.439   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.035   4.727   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.064   0.824   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12   27                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    7   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   12   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24    5   26                                                  
CONECT   26   25                                                            
CONECT   27   24    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₂O₄

Average Mass

368.4330 Da

Monoisotopic Mass

368.17361 Da

IUPAC Name

methyl (1S,15R,17S,18S)-17-ethyl-11-hydroxy-14-oxo-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,15R,17S,18S)-17-ethyl-11-hydroxy-14-oxo-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]1C[C@@H]2C[C@@]3([C@H]1N(CC(O)C1=C3NC3=CC=CC=C13)C2=O)C(=O)OC

InChI Identifier

InChI=1S/C21H24N2O4/c1-3-11-8-12-9-21(20(26)27-2)17-16(13-6-4-5-7-14(13)22-17)15(24)10-23(18(11)21)19(12)25/h4-7,11-12,15,18,22,24H,3,8-10H2,1-2H3/t11-,12+,15?,18-,21+/m0/s1

InChI Key

WPAFASNFOAYXNJ-KFPATTCQSA-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 cymosa	LOTUS Database	35616633
Tabernaemontana peduncularis	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
Azepine
Delta-lactam
Piperidinone
Benzenoid
Piperidine
Heteroaromatic compound
Methyl ester
Tertiary carboxylic acid amide
Pyrrole
Carboxamide group
Carboxylic acid ester
Secondary alcohol
Lactam
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
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	1.83	ChemAxon
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	-0.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.63 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.87 m³·mol⁻¹	ChemAxon
Polarizability	39.43 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

C00025148

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

102239681

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate (NP0277598)

MOL for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D MOL for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D SDF for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D-SDF for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

PDB for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D PDB for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

SMILES for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

INCHI for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

Structure for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D Structure for NP0277598 (methyl (1s,15r,17s,18s)-17-ethyl-11-hydroxy-14-oxo-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)