NP-MRD: Showing NP-Card for Ibogaine (NP0050879)

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Record Information

Version

2.0

Created at

2022-04-27 22:20:02 UTC

Updated at

2022-04-27 22:20:02 UTC

NP-MRD ID

NP0050879

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ibogaine

Description

Ibogaine, also known as endabuse, 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. Ibogaine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Ibogaine is found in Tabernaemontana divaricata, Ervatamia officinalis , Tabernaemontana bovina, Tabernaemontana crassa, Tabernanthe iboga , Trachelospermum jasminoides and Voacanga thouarsii. Ibogaine was first documented in 2007 (PMID: 17698848). Based on a literature review a small amount of articles have been published on ibogaine (PMID: 30471678) (PMID: 18650249) (PMID: 30216039) (PMID: 30471681).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -5.6036    0.0940   -0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838    0.1785   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3218    0.6468    0.1584 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4793   -0.3857    1.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0963   -0.6635    1.8222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4293    0.6881    2.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937    1.2105    0.7114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4473    0.9136    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4632    1.1644    1.2615 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414    0.7863    0.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9592    0.8143    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9469    0.3294    0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6982   -0.1994   -0.9303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7069   -0.6865   -1.7521 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0332   -0.6242   -1.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732   -0.2244   -1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730    0.2616   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904    0.3506   -0.6852 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3195   -0.1299   -1.9380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7398   -1.1456   -1.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5556   -0.7861   -0.4919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3367   -1.4464    0.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8743    0.5914   -0.3520 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6172   -0.0033    0.5627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1373    1.0405   -0.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1373   -0.7981   -0.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0420    0.8113   -1.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8339   -0.8628   -1.2360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5866    1.6462    0.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1085    0.0412    2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9741   -1.3134    0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1548   -1.2404    2.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6100    0.6205    2.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873    1.3893    2.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1079    2.3082    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4019    1.5959    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1759    1.2279    2.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9652    0.3736    0.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7578   -1.1117   -1.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0857   -1.0570   -0.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2689    0.4686   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0901   -0.6202   -2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0540   -0.6546   -2.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743    0.7180   -2.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3692   -1.2899   -2.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -2.1150   -1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527   -2.4414    0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2916   -1.6170    1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8101    1.1455   -1.3005 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 23  1  0
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  2  0
 23  3  1  0
 17 18  1  0
 22  5  1  0
 17 10  1  0
  8  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  1
  4 30  1  0
  4 31  1  0
  5 32  1  1
  6 33  1  0
  6 34  1  0
  7 35  1  1
 23 49  1  6
 22 47  1  0
 22 48  1  0
 20 45  1  0
 20 46  1  0
 19 43  1  0
 19 44  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
M  END


  Mrv1652304282200202D          

 23 27  0  0  1  0            999 V2000
    4.6324   -1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7052   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299    0.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -0.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843   -1.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050   -1.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9808   -0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    0.2282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -0.2350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4310   -1.1245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7271   -1.8624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186   -2.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734   -1.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -0.3913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7214   -0.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -0.6917    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0057   -0.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4996   -0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3077   -1.5168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0557   -1.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 10 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050879

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC1=C3NC2=CC=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13+,17+,20+/m1/s1

> <INCHI_KEY>
HSIBGVUMFOSJPD-CFDPKNGZSA-N

> <FORMULA>
C20H26N2O

> <MOLECULAR_WEIGHT>
310.441

> <EXACT_MASS>
310.204513465

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.680749833577096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
3.5312591903333344

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.082462329312115

> <JCHEM_PKA_STRONGEST_BASIC>
8.967881282952577

> <JCHEM_POLAR_SURFACE_AREA>
28.26

> <JCHEM_REFRACTIVITY>
93.57250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.647  -1.947   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.783  -0.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.522   0.472   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.126  -0.177   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.990  -1.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.251  -2.596   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.489  -2.056   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.698  -0.735   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.709   0.426   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.934  -0.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.805  -2.099   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.357  -3.476   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.648  -4.307   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.057  -3.609   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.728  -2.755   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.605  -0.730   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.213  -1.692   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.685  -0.121   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.348  -1.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.877  -1.473   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.799  -0.239   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.908  -2.831   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.304  -2.182   0.000  0.00  0.00           C+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   17                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   10                                                       
CONECT   18   16   19                                                       
CONECT   19   18   11   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    1   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Value	Source
(-)-Ibogaine	ChEBI
12-Methoxyibogamine	ChEBI
Endabuse	ChEBI
12 Methoxyibogamine	MeSH

Chemical Formula

C₂₀H₂₆N₂O

Average Mass

310.4410 Da

Monoisotopic Mass

310.20451 Da

IUPAC Name

(1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene

Traditional Name

(1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene

CAS Registry Number

Not Available

SMILES

CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC1=C3NC2=CC=C(OC)C=C12

InChI Identifier

InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13+,17+,20+/m1/s1

InChI Key

HSIBGVUMFOSJPD-CFDPKNGZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ervatamia coronaria	LOTUS Database	35616633
Ervatamia officinalis	Plant	KNApSAcK
Tabernaemontana bovina	Plant	KNApSAcK
Tabernaemontana crassa	Plant	KNApSAcK
Tabernanthe iboga	Plant	KNApSAcK
Trachelospermum jasminoides	Plant	KNApSAcK
Voacanga thouarsii	Plant	KNApSAcK

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
3-alkylindole
Pyrroloazepine
Indole
Indole or derivatives
Anisole
Alkyl aryl ether
Azepine
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.23	ALOGPS
logP	3.53	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	17.08	ChemAxon
pKa (Strongest Basic)	8.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.26 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.57 m³·mol⁻¹	ChemAxon
Polarizability	36.68 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00001741

Chemspider ID

170667

KEGG Compound ID

Not Available

BioCyc ID

CPD-21566

BiGG ID

Not Available

Wikipedia Link

Ibogaine

METLIN ID

Not Available

PubChem Compound

197060

PDB ID

Not Available

ChEBI ID

5852

Good Scents ID

Not Available

References

General References

Barsuglia JP, Polanco M, Palmer R, Malcolm BJ, Kelmendi B, Calvey T: A case report SPECT study and theoretical rationale for the sequential administration of ibogaine and 5-MeO-DMT in the treatment of alcohol use disorder. Prog Brain Res. 2018;242:121-158. doi: 10.1016/bs.pbr.2018.08.002. Epub 2018 Oct 25. [PubMed:30471678 ]
Jacobs MT, Zhang YW, Campbell SD, Rudnick G: Ibogaine, a noncompetitive inhibitor of serotonin transport, acts by stabilizing the cytoplasm-facing state of the transporter. J Biol Chem. 2007 Oct 5;282(40):29441-7. doi: 10.1074/jbc.M704456200. Epub 2007 Aug 13. [PubMed:17698848 ]
Maciulaitis R, Kontrimaviciute V, Bressolle FM, Briedis V: Ibogaine, an anti-addictive drug: pharmacology and time to go further in development. A narrative review. Hum Exp Toxicol. 2008 Mar;27(3):181-94. doi: 10.1177/0960327107087802. [PubMed:18650249 ]
Wasko MJ, Witt-Enderby PA, Surratt CK: DARK Classics in Chemical Neuroscience: Ibogaine. ACS Chem Neurosci. 2018 Oct 17;9(10):2475-2483. doi: 10.1021/acschemneuro.8b00294. Epub 2018 Oct 9. [PubMed:30216039 ]
Corkery JM: Ibogaine as a treatment for substance misuse: Potential benefits and practical dangers. Prog Brain Res. 2018;242:217-257. doi: 10.1016/bs.pbr.2018.08.005. Epub 2018 Oct 12. [PubMed:30471681 ]

Showing NP-Card for Ibogaine (NP0050879)

MOL for NP0050879 (Ibogaine)

3D MOL for NP0050879 (Ibogaine)

3D SDF for NP0050879 (Ibogaine)

3D-SDF for NP0050879 (Ibogaine)

PDB for NP0050879 (Ibogaine)

3D PDB for NP0050879 (Ibogaine)

SMILES for NP0050879 (Ibogaine)

INCHI for NP0050879 (Ibogaine)

Structure for NP0050879 (Ibogaine)

3D Structure for NP0050879 (Ibogaine)