NP-MRD: Showing NP-Card for Reserpine (NP0050900)

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Record Information

Version

2.0

Created at

2022-04-27 22:22:17 UTC

Updated at

2024-09-03 04:17:09 UTC

NP-MRD ID

NP0050900

Natural Product DOI

https://doi.org/10.57994/0936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Reserpine

Description

Reserpine, also known as apoplon or serpalan, belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. Reserpine is a very strong basic compound (based on its pKa). Reserpine is a potentially toxic compound. An alkaloid found in the roots of Rauwolfia serpentina and R. Reserpine is found in Alstonia constricta, Alstonia venenata, Alstonia yunnanensis, Nicotiana attenuata, Rauvolfia latifrons, Rauvolfia littoralis, Rauvolfia mannii, Rauvolfia perakensis, Rauvolfia serpentina , Rauvolfia serpentine , Rauvolfia sp., Rauvolfia volkensii, Rauvolfia vomitoria , Rauvolfia yunnanensis, Rauwolfia nitida, Rauwolfia serpentina Benth ex Kurz., Rauwolfia vomitoria and Vinca minor. Vomitoria.

Structure

MOL 3D MOL SDF PDB SMILES InChI

206
  Mrv0541 02231214312D          

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M  END

     RDKit          3D

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M  END

206
  Mrv0541 02231214312D          

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    7.6474    0.1264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2224    0.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8083    0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9109   -0.7290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5553    1.1328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9505    1.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1007    0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7849   -0.9219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3839   -0.2567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7484    1.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8524    2.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4935    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455    2.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3518   -1.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4206    1.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8431   -1.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1111    2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7411    0.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5880    1.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2743    2.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0110    1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0385   -2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5488    0.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0984    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8067   -0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6143   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9060    0.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1639   -0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3226   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1977    1.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5212    0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2001   -0.3590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6583    1.2606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100    0.6457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  6  0  0  0
  1 28  1  0  0  0  0
 20  2  1  1  0  0  0
  2 30  1  0  0  0  0
  3 25  1  0  0  0  0
  3 34  1  0  0  0  0
  4 25  2  0  0  0  0
  5 30  2  0  0  0  0
  6 33  1  0  0  0  0
  6 40  1  0  0  0  0
  7 38  1  0  0  0  0
  7 42  1  0  0  0  0
  8 39  1  0  0  0  0
  8 43  1  0  0  0  0
  9 41  1  0  0  0  0
  9 44  1  0  0  0  0
 10 16  1  0  0  0  0
 10 17  1  0  0  0  0
 10 22  1  0  0  0  0
 11 21  1  0  0  0  0
 11 27  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 12 45  1  6  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 46  1  6  0  0  0
 14 16  1  0  0  0  0
 15 19  1  0  0  0  0
 15 25  1  1  0  0  0
 16 21  1  0  0  0  0
 16 47  1  1  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 29  1  0  0  0  0
 27 31  1  0  0  0  0
 29 32  2  0  0  0  0
 30 35  1  0  0  0  0
 31 33  2  0  0  0  0
 32 33  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 36 39  1  0  0  0  0
 37 38  2  0  0  0  0
 38 41  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=C3C=CC(OC)=C1)C2

> <INCHI_IDENTIFIER>
InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1

> <INCHI_KEY>
QEVHRUUCFGRFIF-MDEJGZGSSA-N

> <FORMULA>
C33H40N2O9

> <MOLECULAR_WEIGHT>
608.6787

> <EXACT_MASS>
608.273380888

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
66.05009821117685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
3.531495942666668

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.29011270669428

> <JCHEM_PKA_STRONGEST_BASIC>
7.559517906091002

> <JCHEM_POLAR_SURFACE_AREA>
117.78

> <JCHEM_REFRACTIVITY>
161.41849999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
reserpine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 206                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.869  -3.187   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      19.024  -0.794   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.182  -3.963   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.221  -2.156   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      19.569   1.818   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.116   2.931   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      24.028  -3.199   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      25.117   2.023   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      26.080  -0.903   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      13.267   3.259   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       9.489   1.538   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      14.275   0.236   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.348   1.428   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.709   0.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.767  -1.361   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.237   2.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.841   2.950   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.988   1.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.398  -1.721   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.517  -0.479   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.730   2.435   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.791   4.724   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.255   3.899   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.285   5.044   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.723  -2.493   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.724   3.895   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.252   2.439   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.374  -3.513   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.674   5.096   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.050   0.355   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.698   2.082   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.112   4.775   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.621   3.258   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.139  -5.096   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.558   0.041   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.584   1.189   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.039  -1.422   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.547  -1.737   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      24.091   0.874   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.080   4.070   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      24.573  -0.588   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      23.002  -4.348   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      24.636   3.486   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      27.106   0.246   0.000  0.00  0.00           C+0
HETATM   45  H   UNK     0      13.440  -0.670   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      16.162   2.353   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      11.405   1.205   0.000  0.00  0.00           H+0
CONECT    1   19   28                                                       
CONECT    2   20   30                                                       
CONECT    3   25   34                                                       
CONECT    4   25                                                            
CONECT    5   30                                                            
CONECT    6   33   40                                                       
CONECT    7   38   42                                                       
CONECT    8   39   43                                                       
CONECT    9   41   44                                                       
CONECT   10   16   17   22                                                  
CONECT   11   21   27                                                       
CONECT   12   13   14   15   45                                             
CONECT   13   12   17   18   46                                             
CONECT   14   12   16                                                       
CONECT   15   12   19   25                                                  
CONECT   16   10   14   21   47                                             
CONECT   17   10   13                                                       
CONECT   18   13   20                                                       
CONECT   19    1   15   20                                                  
CONECT   20    2   18   19                                                  
CONECT   21   11   16   23                                                  
CONECT   22   10   24                                                       
CONECT   23   21   24   26                                                  
CONECT   24   22   23                                                       
CONECT   25    3    4   15                                                  
CONECT   26   23   27   29                                                  
CONECT   27   11   26   31                                                  
CONECT   28    1                                                            
CONECT   29   26   32                                                       
CONECT   30    2    5   35                                                  
CONECT   31   27   33                                                       
CONECT   32   29   33                                                       
CONECT   33    6   31   32                                                  
CONECT   34    3                                                            
CONECT   35   30   36   37                                                  
CONECT   36   35   39                                                       
CONECT   37   35   38                                                       
CONECT   38    7   37   41                                                  
CONECT   39    8   36   41                                                  
CONECT   40    6                                                            
CONECT   41    9   38   39                                                  
CONECT   42    7                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   16                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

View in JSmol

Synonyms

Value	Source
(-)-Reserpine	ChEBI
(3beta,16beta,17alpha,18beta,20alpha)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	ChEBI
3,4,5-Trimethoxybenzoyl methyl reserpate	ChEBI
Apoplon	ChEBI
Reserpin	ChEBI
Serpalan	ChEBI
(3b,16b,17a,18b,20a)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3b,16b,17a,18b,20a)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	Generator
(3beta,16beta,17alpha,18beta,20alpha)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3Β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3Β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	Generator
3,4,5-Trimethoxybenzoyl methyl reserpic acid	Generator
Rausedil	HMDB
Serpasil	HMDB
V Serp	HMDB
V-Serp	HMDB
Raupasil	HMDB
Serpivite	HMDB
Raunervil	HMDB
Vitarine brand OF reserpine	HMDB
Rausedyl	HMDB
Vangarde brand OF reserpine	HMDB

Chemical Formula

C₃₃H₄₀N₂O₉

Average Mass

608.6787 Da

Monoisotopic Mass

608.27338 Da

IUPAC Name

methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

Traditional Name

reserpine

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=C3C=CC(OC)=C1)C2

InChI Identifier

InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1

InChI Key

QEVHRUUCFGRFIF-MDEJGZGSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-19	View Spectrum

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
Alstonia constricta	LOTUS Database	35616633
Alstonia venenata	LOTUS Database	35616633
Alstonia yunnanensis	Plant	KNApSAcK
Nicotiana attenuata	LOTUS Database	35616633
Rauvolfia latifrons	Plant	KNApSAcK
Rauvolfia littoralis	LOTUS Database	35616633
Rauvolfia mannii	LOTUS Database	35616633
Rauvolfia perakensis	Plant	KNApSAcK
Rauvolfia serpentina	Plant	KNApSAcK
Rauvolfia serpentine	Plant	KNApSAcK
Rauvolfia sp.	Plant	KNApSAcK
Rauvolfia volkensii	LOTUS Database	35616633
Rauvolfia vomitoria	Plant	KNApSAcK
Rauvolfia yunnanensis	Plant	KNApSAcK
Rauwolfia nitida	Plant	KNApSAcK
Rauwolfia serpentina Benth ex Kurz.	Plant	KNApSAcK
Rauwolfia vomitoria	Plant	KNApSAcK
Vinca minor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Yohimbine
Corynanthean skeleton
Yohimbine alkaloid
Pyridoindole
Beta-carboline
Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
Benzoate ester
3-alkylindole
Indole
Indole or derivatives
Benzoic acid or derivatives
Benzoyl
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Piperidine
Pyrrole
Methyl ester
Heteroaromatic compound
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxylic acid ester
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Azacycle
Dialkyl ether
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid ester (CHEBI:28487 )
yohimban alkaloid (CHEBI:28487 )
Indole alkaloids (C06539 )
Alkaloids (C06539 )

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	4.05	ALOGPS
logP	3.53	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.29	ChemAxon
pKa (Strongest Basic)	7.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.78 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	161.42 m³·mol⁻¹	ChemAxon
Polarizability	66.05 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon