NP-MRD: Showing NP-Card for methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate (NP0154435)

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Record Information

Version

2.0

Created at

2022-09-02 11:14:30 UTC

Updated at

2022-09-02 11:14:30 UTC

NP-MRD ID

NP0154435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]Nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate 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 17-ethyl-6-hydroxy-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 calcarea. Methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]Nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514462D          

 26 30  0  0  0  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  0  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
    5.3047    1.3954    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  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  0  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  2  1  0  0  0  0
  2  3  1  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
  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
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 10 19  1  0  0  0  0
 13 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
  7 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
   -4.2688   -2.7735    1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8197   -2.4704    0.9025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173   -0.9949    0.7920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2156   -0.3375   -0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2764   -0.0690   -1.5016 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5087   -1.3604   -1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018   -1.7131   -0.6440 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090   -2.2088   -0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4479   -1.2534   -1.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677   -0.1477   -0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920    0.6125    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613    1.4837    0.8730 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9495    1.2944    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1141    1.8997    1.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3520    1.5131    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4916    2.1561    1.0478 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4324    0.4830   -0.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2834   -0.1572   -0.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    0.2708   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890    0.5238    0.2218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0397    1.5387    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6194    1.3339    2.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7749    2.8719    0.8672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1312    3.9497    1.6740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144    0.9307   -1.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219   -0.8693    0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7436   -2.1056    1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8553   -2.7943    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470   -3.8040    1.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4503   -3.0541    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -2.9157    1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8098   -0.5502    1.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1376   -0.8427   -0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5446    0.6799    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288    0.2976   -2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2294   -2.1314   -2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8891   -1.1320   -2.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4718   -3.1656   -1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -2.4313    0.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -0.9209   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3928   -1.8468   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3306    2.2079    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0817    2.7204    1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9403    1.7790    1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4027    0.1690   -0.6962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3726   -0.9621   -1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474    4.0327    2.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938    4.8683    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376    3.8232    2.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074    0.9753   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815    1.9262   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -1.3297    1.3505 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
 15 17  2  0
 17 18  1  0
 18 19  2  0
 11 20  1  0
 20 25  1  0
 20 26  1  0
 20 21  1  1
 21 22  2  0
 21 23  1  0
 23 24  1  0
 26  3  1  0
 25  5  1  0
 26  7  1  0
 19 10  1  0
 19 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  1
  4 33  1  0
  4 34  1  0
  5 35  1  6
  6 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
  9 41  1  0
 12 42  1  0
 14 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  1
 24 47  1  0
 24 48  1  0
 24 49  1  0
M  END


  Mrv1533004231514462D          

 26 30  0  0  0  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  0  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
    5.3047    1.3954    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  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  0  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  2  1  0  0  0  0
  2  3  1  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
  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
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 10 19  1  0  0  0  0
 13 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
  7 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CC2CN3CCC4=C(NC5=CC(O)=CC=C45)C(C2)(C13)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c1-3-13-8-12-10-21(20(25)26-2)18-16(6-7-23(11-12)19(13)21)15-5-4-14(24)9-17(15)22-18/h4-5,9,12-13,19,22,24H,3,6-8,10-11H2,1-2H3

> <INCHI_KEY>
GFEUNVMURRUASI-UHFFFAOYSA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.43418424668463

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
2.9852243455484473

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.299147548590923

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.561375051924554

> <JCHEM_PKA_STRONGEST_BASIC>
8.457055953533429

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
99.91939999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         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       9.902   2.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.419   3.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.318   1.944   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.616   0.354   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.770   1.639   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.059   0.818   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.516  -1.183   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.135  -1.864   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.796  -2.038   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.696  -3.575   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   10   13                                                  
CONECT   20   11   21   22   23                                             
CONECT   21   20    5                                                       
CONECT   22   20    3    7                                                  
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
Methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0,.0,.0,]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylic acid	Generator
Methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCC1CC2CN3CCC4=C(NC5=CC(O)=CC=C45)C(C2)(C13)C(=O)OC

InChI Identifier

InChI=1S/C21H26N2O3/c1-3-13-8-12-10-21(20(25)26-2)18-16(6-7-23(11-12)19(13)21)15-5-4-14(24)9-17(15)22-18/h4-5,9,12-13,19,22,24H,3,6-8,10-11H2,1-2H3

InChI Key

GFEUNVMURRUASI-UHFFFAOYSA-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 calcarea	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
Hydroxyindole
Pyrroloazepine
3-alkylindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
Azepine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Piperidine
Benzenoid
Methyl ester
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Amine
Organonitrogen 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	3.62	ALOGPS
logP	2.99	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	8.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.92 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

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

14108845

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate (NP0154435)

MOL for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D MOL for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D SDF for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D-SDF for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

PDB for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D PDB for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

SMILES for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

INCHI for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

Structure for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)

3D Structure for NP0154435 (methyl 17-ethyl-6-hydroxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate)