NP-MRD: Showing NP-Card for Reserpin N-oxide (NP0138805)

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Record Information

Version

1.0

Created at

2022-06-29 19:17:53 UTC

Updated at

2022-06-29 19:17:53 UTC

NP-MRD ID

NP0138805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Reserpin N-oxide

Description

474-48-6 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. Reserpin N-oxide is found in Rauvolfia serpentina. Based on a literature review very few articles have been published on 474-48-6.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221172D          

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  1  2  1  0  0  0  0
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M  CHG  2   8   1  30  -1
M  END

     RDKit          3D

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M  CHG  2  22   1  23  -1
M  END


  Mrv1652306292221172D          

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    5.1175    1.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6559    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069    2.1239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348    2.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    0.9538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606    0.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0316    0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365    0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6414    1.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875    1.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0465   -1.4628    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.2829    0.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8213    0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5491    1.5090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6318    0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1702    1.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9808    1.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2529    0.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7145   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9040   -0.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9867   -1.1350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4483   -1.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0635    0.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6019    0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5192    1.6729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3297    1.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  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  1  0  0  0  0
 11 12  2  0  0  0  0
 13 12  1  1  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 30  1  0  0  0  0
  4 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  0  0  0  0
 36 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  CHG  2   8   1  30  -1
M  END
> <DATABASE_ID>
NP0138805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@@H](C[C@@H]2C[N+]3([O-])CCC4=C(NC5=C4C=CC(OC)=C5)[C@H]3C[C@@H]2[C@@H]1C(=O)OC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H40N2O10/c1-39-19-7-8-20-21-9-10-35(38)16-18-13-27(45-32(36)17-11-25(40-2)30(42-4)26(12-17)41-3)31(43-5)28(33(37)44-6)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+,35?/m1/s1

> <INCHI_KEY>
VRKGMHQUKPFVFT-DMUFBCNISA-N

> <FORMULA>
C33H40N2O10

> <MOLECULAR_WEIGHT>
624.687

> <EXACT_MASS>
624.268295496

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
66.90843849989298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-19-(methoxycarbonyl)-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraen-13-ium-13-olate

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.407120759333335

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.858188023340244

> <JCHEM_PKA_STRONGEST_BASIC>
3.2343980696638717

> <JCHEM_POLAR_SURFACE_AREA>
137.6

> <JCHEM_REFRACTIVITY>
163.46339999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-19-(methoxycarbonyl)-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraen-13-ium-13-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      12.071   4.557   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.579   3.104   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.574   1.937   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.082   0.483   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.077  -0.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.564  -0.397   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.559  -1.564   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       7.046  -1.277   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0       6.041  -2.444   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.527  -2.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.019  -0.703   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.025   0.464   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.538   0.177   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.543   1.344   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.056   1.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.061   2.224   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.553   3.678   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.558   4.844   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.040   3.965   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.532   5.418   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       4.225   1.780   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.726   1.427   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.599  -0.108   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.206  -0.765   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.059   0.113   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.068   1.648   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.461   2.305   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.197   2.525   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.590   1.868   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.554  -2.731   0.000  0.00  0.00           O-1
HETATM   31  O   UNK     0      13.595   0.196   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.600   1.363   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.092   2.817   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.113   1.076   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.118   2.243   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.631   1.956   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      19.139   0.502   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      18.134  -0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.621  -0.378   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      18.642  -2.119   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      17.637  -3.285   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      20.652   0.215   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      21.657   1.382   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      19.636   3.123   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      21.149   2.836   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13   30                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15    3   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30    8                                                            
CONECT   31    4   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   44                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38   34                                                       
CONECT   40   38   41                                                       
CONECT   41   40                                                            
CONECT   42   37   43                                                       
CONECT   43   42                                                            
CONECT   44   36   45                                                       
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₀N₂O₁₀

Average Mass

624.6870 Da

Monoisotopic Mass

624.26830 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

474-48-6

SMILES

CO[C@H]1[C@@H](C[C@@H]2C[N+]3([O-])CCC4=C(NC5=C4C=CC(OC)=C5)[C@H]3C[C@@H]2[C@@H]1C(=O)OC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C33H40N2O10/c1-39-19-7-8-20-21-9-10-35(38)16-18-13-27(45-32(36)17-11-25(40-2)30(42-4)26(12-17)41-3)31(43-5)28(33(37)44-6)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+,35?/m1/s1

InChI Key

VRKGMHQUKPFVFT-DMUFBCNISA-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
Rauvolfia serpentina	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
Benzoic acid or derivatives
Indole
Indole or derivatives
Phenoxy compound
Methoxybenzene
Benzoyl
Phenol ether
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Piperidine
Pyrrole
Methyl ester
Trialkyl amine oxide
Heteroaromatic compound
Carboxylic acid ester
Trisubstituted n-oxide
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
N-oxide
Ether
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic zwitterion
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
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

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

58798804

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12442718

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Reserpin N-oxide (NP0138805)

MOL for NP0138805 (Reserpin N-oxide)

3D MOL for NP0138805 (Reserpin N-oxide)

3D SDF for NP0138805 (Reserpin N-oxide)

3D-SDF for NP0138805 (Reserpin N-oxide)

PDB for NP0138805 (Reserpin N-oxide)

3D PDB for NP0138805 (Reserpin N-oxide)

SMILES for NP0138805 (Reserpin N-oxide)

INCHI for NP0138805 (Reserpin N-oxide)

Structure for NP0138805 (Reserpin N-oxide)

3D Structure for NP0138805 (Reserpin N-oxide)