NP-MRD: Showing NP-Card for 10-Hydroxycoronaridine (NP0067870)

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Record Information

Version

2.0

Created at

2022-04-28 12:42:41 UTC

Updated at

2022-04-28 12:42:41 UTC

NP-MRD ID

NP0067870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-Hydroxycoronaridine

Description

10-Hydroxycoronaridine 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. 10-Hydroxycoronaridine 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. 10-Hydroxycoronaridine is found in Tabernaemontana echinata Vell. 10-Hydroxycoronaridine was first documented in 2000 (PMID: 10763593). Based on a literature review a small amount of articles have been published on 10-hydroxycoronaridine (PMID: 35052998).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214422D          

 26 30  0  0  1  0            999 V2000
    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
    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
    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
    5.3077   -1.5168    0.0000 O   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
   -1.3310   -1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    0.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    1.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070    0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310    1.3813    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  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
  7 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 11 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 11 23  1  1  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
   -4.8179   -1.7736    0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3837   -1.7976    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8262   -0.3942   -0.0335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9301    0.2924    1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5970    0.9711    1.6596 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6332   -0.1825    1.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8491   -1.1617    0.9650 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0937   -2.1946    0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -2.0200   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835   -0.6202   -0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8339    0.5194   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7117    1.5596   -0.2443 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9577    1.0869   -0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2025    1.6905    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410    0.9253    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2910   -0.4482    0.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026   -1.2592    0.4728 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0579   -1.0416    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9084   -0.2784   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270    0.6873   -0.5533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8372    1.1756   -1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4968    0.5852   -2.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517    2.3871   -2.2766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3838    2.9530   -3.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1744    1.7235    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.6086   -0.2756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3673   -1.0063    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2318   -2.7949    0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896   -1.5849    1.7285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7490   -2.2869    0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -2.3576   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3012    0.1551   -0.8381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7698    1.0026    1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004   -0.4370    2.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    1.6609    2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3987    0.1717    2.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9743   -0.5958    2.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4521   -3.1550    0.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895   -2.3604    1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6986   -2.3077   -1.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9380   -2.7285   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    2.5626   -0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735    2.7682    0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3063    1.4080    0.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7312   -1.5667    1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9329   -2.0997    0.1448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4568    2.6946   -4.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3544    4.0612   -3.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758    2.7329   -4.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014    2.1291   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4336    2.5175    0.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2018   -1.3595   -1.0770 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  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11 20  1  0
 20 25  1  0
 20 26  1  0
 20 21  1  6
 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  6
  4 33  1  0
  4 34  1  0
  5 35  1  1
  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
 15 44  1  0
 17 45  1  0
 18 46  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  6
 24 47  1  0
 24 48  1  0
 24 49  1  0
M  END


  Mrv1652304282214422D          

 26 30  0  0  1  0            999 V2000
    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
    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
    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
    5.3077   -1.5168    0.0000 O   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
   -1.3310   -1.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    0.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    1.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070    0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310    1.3813    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  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
  7 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 11 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 11 23  1  1  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>
NP0067870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1C[C@H]2CN3CCC4=C(NC5=CC=C(O)C=C45)[C@](C2)([C@H]13)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c1-3-13-8-12-10-21(20(25)26-2)18-15(6-7-23(11-12)19(13)21)16-9-14(24)4-5-17(16)22-18/h4-5,9,12-13,19,22,24H,3,6-8,10-11H2,1-2H3/t12-,13+,19+,21-/m1/s1

> <INCHI_KEY>
TUZCJNZERFWZAS-YDBSYXHISA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.415998647163406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
2.9964493816095876

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.430381515762612

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.588625817090797

> <JCHEM_PKA_STRONGEST_BASIC>
8.4417049436587

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
99.9194

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,15R,17S,18S)-17-ethyl-7-hydroxy-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                                 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       4.489  -2.056   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.698  -0.735   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.709   0.426   0.000  0.00  0.00           N+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       8.647  -1.947   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.783  -0.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.522   0.472   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.908  -2.831   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.934  -0.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.805  -2.099   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.357  -3.476   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.648  -4.307   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.057  -3.609   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.728  -2.755   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.605  -0.730   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.213  -1.692   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.685  -0.121   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.348  -1.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.877  -1.473   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.485  -2.888   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.329   0.978   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.253   2.209   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.200   1.162   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.804   2.578   0.000  0.00  0.00           C+0
CONECT    1    2    5   15                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7                                                            
CONECT   11    2   12   18   23                                             
CONECT   12   11   13   20                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    1                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   11                                                       
CONECT   19   17   20                                                       
CONECT   20   19   12   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   11   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

Not Available

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

methyl (1S,15R,17S,18S)-17-ethyl-7-hydroxy-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-7-hydroxy-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]2CN3CCC4=C(NC5=CC=C(O)C=C45)[C@](C2)([C@H]13)C(=O)OC

InChI Identifier

InChI=1S/C21H26N2O3/c1-3-13-8-12-10-21(20(25)26-2)18-15(6-7-23(11-12)19(13)21)16-9-14(24)4-5-17(16)22-18/h4-5,9,12-13,19,22,24H,3,6-8,10-11H2,1-2H3/t12-,13+,19+,21-/m1/s1

InChI Key

TUZCJNZERFWZAS-YDBSYXHISA-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
Tabernaemontana echinata Vell.	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
Pyrroloazepine
3-alkylindole
Hydroxyindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
Azepine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Methyl ester
Pyrrole
Carboxylic acid ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Organic oxide
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	3.61	ALOGPS
logP	3	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	8.44	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	39.42 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

C00025704

Chemspider ID

138080

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156852

PDB ID

Not Available

ChEBI ID

146256

Good Scents ID

Not Available

References

General References

Ngah L, Tsopgni WDT, Nyobe JCN, Tcho AT, Langat MK, Ndom JC, Mas-Claret E, Sadgrove NJ, Waffo AFK, Phumthum M: A New Antimicrobial Phenylpropanol from the Leaves of Tabernaemontana inconspicua Stapf. (Apocynaceae) Inhibits Pathogenic Gram-Negative Bacteria. Antibiotics (Basel). 2022 Jan 17;11(1). pii: antibiotics11010121. doi: 10.3390/antibiotics11010121. [PubMed:35052998 ]
Masuda K, Akiyama T, Taki M, Takaishi S, Iijima Y, Yamazaki M, Aimi N, Jato J, Waterman PG: Isolation of 10-hydroxycoronaridine from Tabernaemontana penduliflora and its estrogen-like activity. Planta Med. 2000 Mar;66(2):169-71. doi: 10.1055/s-2000-11132. [PubMed:10763593 ]

Showing NP-Card for 10-Hydroxycoronaridine (NP0067870)

MOL for NP0067870 (10-Hydroxycoronaridine)

3D MOL for NP0067870 (10-Hydroxycoronaridine)

3D SDF for NP0067870 (10-Hydroxycoronaridine)

3D-SDF for NP0067870 (10-Hydroxycoronaridine)

PDB for NP0067870 (10-Hydroxycoronaridine)

3D PDB for NP0067870 (10-Hydroxycoronaridine)

SMILES for NP0067870 (10-Hydroxycoronaridine)

INCHI for NP0067870 (10-Hydroxycoronaridine)

Structure for NP0067870 (10-Hydroxycoronaridine)

3D Structure for NP0067870 (10-Hydroxycoronaridine)