NP-MRD: Showing NP-Card for Norrauvomitine (NP0066698)

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Record Information

Version

2.0

Created at

2022-04-28 10:56:49 UTC

Updated at

2022-04-28 10:56:49 UTC

NP-MRD ID

NP0066698

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Norrauvomitine

Description

(1R,9R,10S,12R,13E,16S,17S,18S)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoate belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether. Norrauvomitine is found in Rauvolfia vomitoria . Based on a literature review very few articles have been published on (1R,9R,10S,12R,13E,16S,17S,18S)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212562D          

 36 42  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282212562D          

 36 42  0  0  1  0            999 V2000
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 11 20  1  0  0  0  0
 14 21  1  0  0  0  0
  7 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066698

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C(=O)O[C@H]1[C@@H]2[C@@H]3C[C@@]11[C@@H](NC4=CC=CC=C14)[C@@H]1C[C@H]2\C(CN31)=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C29H32N2O5/c1-5-15-14-31-20-12-17(15)24-21(31)13-29(18-8-6-7-9-19(18)30-26(20)29)27(24)36-28(32)16-10-22(33-2)25(35-4)23(11-16)34-3/h5-11,17,20-21,24,26-27,30H,12-14H2,1-4H3/b15-5-/t17-,20-,21-,24-,26-,27-,29+/m0/s1

> <INCHI_KEY>
CKVGOUASLXKGHJ-PHINDKHXSA-N

> <FORMULA>
C29H32N2O5

> <MOLECULAR_WEIGHT>
488.584

> <EXACT_MASS>
488.231122138

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.12144784865709

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9R,10S,12R,13E,16S,17S,18S)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoate

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.3887770306666676

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.924081326760017

> <JCHEM_PKA_STRONGEST_BASIC>
7.426613366669793

> <JCHEM_POLAR_SURFACE_AREA>
69.26

> <JCHEM_REFRACTIVITY>
137.23049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10S,12R,13E,16S,17S,18S)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoate

> <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       7.626   3.299   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.763   1.765   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.503   0.879   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.106   1.527   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.969   3.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.229   3.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.458   3.574   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.817   2.058   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.727   0.849   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.267   2.113   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.083   3.778   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.046   4.706   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.606   4.974   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.910   3.288   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.584   1.650   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.500   0.948   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.986   2.293   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.414   1.717   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.629   0.192   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.436   3.696   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.259   2.835   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.435   1.305   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.197   0.388   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.336   0.535   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.373  -1.142   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.785  -1.755   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.961  -3.285   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.723  -4.202   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.311  -3.589   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.135  -2.059   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.927  -4.505   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.339  -3.892   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.899  -5.732   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.311  -6.345   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.373  -3.898   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.549  -5.428   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
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   13   21                                             
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   16                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    7                                                       
CONECT   14   12   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   10                                                       
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   11                                                       
CONECT   21   14    7   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28   34                                                       
CONECT   34   33                                                            
CONECT   35   27   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1R,9R,10S,12R,13E,16S,17S,18S)-13-Ethylidene-8,15-diazahexacyclo[14.2.1.0,.0,.0,.0,]nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoic acid	Generator

Chemical Formula

C₂₉H₃₂N₂O₅

Average Mass

488.5840 Da

Monoisotopic Mass

488.23112 Da

IUPAC Name

(1R,9R,10S,12R,13E,16S,17S,18S)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoate

Traditional Name

(1R,9R,10S,12R,13E,16S,17S,18S)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-yl 3,4,5-trimethoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C(=O)O[C@H]1[C@@H]2[C@@H]3C[C@@]11[C@@H](NC4=CC=CC=C14)[C@@H]1C[C@H]2\C(CN31)=C/C

InChI Identifier

InChI=1S/C29H32N2O5/c1-5-15-14-31-20-12-17(15)24-21(31)13-29(18-8-6-7-9-19(18)30-26(20)29)27(24)36-28(32)16-10-22(33-2)25(35-4)23(11-16)34-3/h5-11,17,20-21,24,26-27,30H,12-14H2,1-4H3/b15-5-/t17-,20-,21-,24-,26-,27-,29+/m0/s1

InChI Key

CKVGOUASLXKGHJ-PHINDKHXSA-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
Rauvolfia vomitoria	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ajmaline-sarpagine alkaloids

Sub Class

Not Available

Direct Parent

Ajmaline-sarpagine alkaloids

Alternative Parents

Substituents

Sarpagine-skeleton
Pyridoindole
Beta-carboline
Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
Quinolizidine
Benzoate ester
Dihydroindole
Indole or derivatives
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Quinuclidine
Phenol ether
Benzoyl
Anisole
Aralkylamine
Secondary aliphatic/aromatic amine
Azepane
Alkyl aryl ether
Benzenoid
Piperidine
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	3.8	ALOGPS
logP	3.39	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.92	ChemAxon
pKa (Strongest Basic)	7.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.26 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	137.23 m³·mol⁻¹	ChemAxon
Polarizability	53.12 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163103676

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Norrauvomitine (NP0066698)

MOL for NP0066698 (Norrauvomitine)

3D MOL for NP0066698 (Norrauvomitine)

3D SDF for NP0066698 (Norrauvomitine)

3D-SDF for NP0066698 (Norrauvomitine)

PDB for NP0066698 (Norrauvomitine)

3D PDB for NP0066698 (Norrauvomitine)

SMILES for NP0066698 (Norrauvomitine)

INCHI for NP0066698 (Norrauvomitine)

Structure for NP0066698 (Norrauvomitine)

3D Structure for NP0066698 (Norrauvomitine)