NP-MRD: Showing NP-Card for 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 (NP0321871)

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Record Information

Version

2.0

Created at

2022-09-12 00:18:38 UTC

Updated at

2022-09-12 00:18:38 UTC

NP-MRD ID

NP0321871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

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. 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. 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 a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241512102D          

 36 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241512102D          

 36 42  0  0  0  0            999 V2000
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    3.3899   -0.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0354    0.0925    0.0000 C   0  0  0  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
    5.5387   -1.3033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7618   -2.0976    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  0  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  0  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  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 29  1  0  0  0  0
 19 29  1  0  0  0  0
 27 30  1  0  0  0  0
  3 30  1  0  0  0  0
 19 30  1  0  0  0  0
 25 31  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1CC2(C)CCC(OC(=O)C3=CC=CC=C3)C34C5CC6C(OC)C5C(O)(CC6OC)C(CC23)C14

> <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

> <INCHI_KEY>
GNNQINKXWHFSIK-UHFFFAOYSA-N

> <FORMULA>
C30H41NO5

> <MOLECULAR_WEIGHT>
495.66

> <EXACT_MASS>
495.298473424

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.59852086559406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.8628455939999995

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.125885441957973

> <JCHEM_PKA_STRONGEST_BASIC>
9.990753785513558

> <JCHEM_POLAR_SURFACE_AREA>
68.23

> <JCHEM_REFRACTIVITY>
136.33350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         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  C   UNK     0       7.691  -3.146   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.171  -2.762   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.174  -4.302   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.477  -3.195   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.595  -2.558   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.766  -0.872   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.401  -2.823   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.328  -1.209   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.533   0.173   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.398   1.707   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.659   2.591   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.339  -2.433   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.755  -3.915   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   29                                             
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   29   30                                             
CONECT   20   19   21   31                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28    5   19                                                  
CONECT   30   27    3   19                                                  
CONECT   31   25   20   32                                                  
CONECT   32   31   22   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   23   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Value	Source
11-Ethyl-8-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-16-yl benzoic acid	Generator
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 benzoic acid	Generator

Chemical Formula

C₃₀H₄₁NO₅

Average Mass

495.6600 Da

Monoisotopic Mass

495.29847 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCN1CC2(C)CCC(OC(=O)C3=CC=CC=C3)C34C5CC6C(OC)C5C(O)(CC6OC)C(CC23)C14

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

InChI Key

GNNQINKXWHFSIK-UHFFFAOYSA-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
logP	2.9	ALOGPS
logP	2.86	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	9.99	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.33 m³·mol⁻¹	ChemAxon
Polarizability	55.6 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 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 (NP0321871)

MOL for NP0321871 (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 NP0321871 (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 NP0321871 (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 NP0321871 (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 NP0321871 (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 NP0321871 (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 NP0321871 (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 NP0321871 (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 NP0321871 (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 NP0321871 (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)