NP-MRD: Showing NP-Card for (1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate (NP0252997)

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Record Information

Version

2.0

Created at

2022-09-07 16:43:22 UTC

Updated at

2022-09-07 16:43:22 UTC

NP-MRD ID

NP0252997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate

Description

(1S,2R,3R,4S,5R,6S,8S,9S,10R,13S,16S,17R)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-16-yl benzoate belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. (1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate is found in Aconitum karakolicum. Based on a literature review very few articles have been published on (1S,2R,3R,4S,5R,6S,8S,9S,10R,13S,16S,17R)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-16-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072218432D          

 36 42  0  0  1  0            999 V2000
   -0.3274   -2.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -2.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.6043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4197   -0.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0090    0.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0155    0.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8202    0.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3453    0.3251    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1498    0.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937    1.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  9 19  1  0  0  0  0
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 29 30  1  1  0  0  0
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  5 31  1  0  0  0  0
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 33 20  1  6  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 77 83  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309072218432D          

 36 42  0  0  1  0            999 V2000
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    3.3060   -1.4797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3073   -2.3047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3984   -1.7119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3902   -1.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4816   -0.4669    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8221   -1.5122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3899   -0.6478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0354    0.0925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9630    0.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386    1.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  6  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 31 30  1  6  0  0  0
  5 31  1  0  0  0  0
 19 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32  3  1  1  0  0  0
 19 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 20  1  6  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(C)CC[C@H](OC(=O)C3=CC=CC=C3)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@H](C[C@H]23)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C30H41NO5/c1-5-31-16-28(2)12-11-23(36-27(32)17-9-7-6-8-10-17)30-19-13-18-21(34-3)15-29(33,24(19)25(18)35-4)20(26(30)31)14-22(28)30/h6-10,18-26,33H,5,11-16H2,1-4H3/t18-,19-,20+,21+,22-,23+,24-,25+,26-,28-,29+,30-/m1/s1

> <INCHI_KEY>
GNNQINKXWHFSIK-FQYKMUNDSA-N

> <FORMULA>
C30H41NO5

> <MOLECULAR_WEIGHT>
495.66

> <EXACT_MASS>
495.298473424

> <ALOGPS_LOGP>
2.90

> <ALOGPS_LOGS>
-4.47

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.611  -4.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.926  -4.371   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.618  -2.995   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.783  -1.614   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.460  -0.167   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.017   0.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.896   1.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.398   1.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.378   0.607   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.880   0.948   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.335   2.419   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.837   2.760   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.289   3.549   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.787   3.208   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.741   4.338   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.196   5.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.698   6.150   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.744   5.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.985  -0.999   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.447  -0.204   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.805   0.849   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.334  -0.473   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.847  -2.052   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.339  -2.433   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.755  -3.915   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.691  -3.146   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.171  -2.762   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.174  -4.302   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.477  -3.195   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.595  -2.558   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.766  -0.872   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.401  -2.823   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.328  -1.209   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.533   0.173   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.398   1.707   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.659   2.591   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   31                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    9   20   31   32                                             
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   29   33                                             
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30    5   19                                                  
CONECT   32   29    3   19                                                  
CONECT   33   27   20   34                                                  
CONECT   34   33   22   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,4S,5R,6S,8S,9S,10R,13S,16S,17R)-11-Ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-16-yl benzoic acid	Generator

Chemical Formula

C₃₀H₄₁NO₅

Average Mass

495.6600 Da

Monoisotopic Mass

495.29847 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(C)CC[C@H](OC(=O)C3=CC=CC=C3)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@H](C[C@H]23)[C@@H]14

InChI Identifier

InChI=1S/C30H41NO5/c1-5-31-16-28(2)12-11-23(36-27(32)17-9-7-6-8-10-17)30-19-13-18-21(34-3)15-29(33,24(19)25(18)35-4)20(26(30)31)14-22(28)30/h6-10,18-26,33H,5,11-16H2,1-4H3/t18-,19-,20+,21+,22-,23+,24-,25+,26-,28-,29+,30-/m1/s1

InChI Key

GNNQINKXWHFSIK-FQYKMUNDSA-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
Aconitum karakolicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Benzoate ester
Quinolidine
Benzoic acid or derivatives
Alkaloid or derivatives
Benzoyl
Azepane
Monocyclic benzene moiety
Benzenoid
Piperidine
Tertiary alcohol
Cyclic alcohol
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Amine
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
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

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

163189678

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate (NP0252997)

MOL for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

3D MOL for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

3D SDF for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

3D-SDF for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

PDB for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

3D PDB for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

SMILES for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

INCHI for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

Structure for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)

3D Structure for NP0252997 ((1s,2r,3r,4s,5r,6s,8s,9s,10r,13s,16s,17r)-11-ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-16-yl benzoate)