NP-MRD: Showing NP-Card for 11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate (NP0249049)

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Record Information

Version

2.0

Created at

2022-09-07 11:30:15 UTC

Updated at

2022-09-07 11:30:15 UTC

NP-MRD ID

NP0249049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate

Description

11-Ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-yl acetate 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-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate is found in Aconitum variegatum. 11-Ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-yl acetate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518472D          

 32 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004231518472D          

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 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1CC2(C)CCC(OC)C34C2CC(C13)C1(O)CC(OC)C2CC4(O)C1C2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H39NO6/c1-6-26-12-22(3)8-7-18(31-5)25-17(22)9-15(21(25)26)23(28)11-16(30-4)14-10-24(25,29)20(23)19(14)32-13(2)27/h14-21,28-29H,6-12H2,1-5H3

> <INCHI_KEY>
NETXKASDOZAODV-UHFFFAOYSA-N

> <FORMULA>
C25H39NO6

> <MOLECULAR_WEIGHT>
449.588

> <EXACT_MASS>
449.27773798

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
48.94868645633308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
-0.08954945833333335

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.358287280808298

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.63789486119488

> <JCHEM_PKA_STRONGEST_BASIC>
9.840159261801281

> <JCHEM_POLAR_SURFACE_AREA>
88.46000000000001

> <JCHEM_REFRACTIVITY>
116.83029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -2.560   1.802   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.007   1.430   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.386  -0.162   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.220  -1.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.543  -2.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.051  -3.593   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.108  -4.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.394  -4.958   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.375  -3.764   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.240  -5.490   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.991  -6.987   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.981  -2.157   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.762  -2.285   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.591  -0.598   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.473   0.039   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.398  -0.333   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.167  -0.394   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.027   1.222   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.687  -0.011   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.842  -1.104   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.414  -0.706   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.100   0.702   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.329  -2.683   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.801  -4.005   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.442  -2.953   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.699  -4.676   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.324  -1.947   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.528  -3.329   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.785  -4.384   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.098  -5.308   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.495  -4.660   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.961  -6.842   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   16   25                                             
CONECT   13   12    5   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15    3   12                                                  
CONECT   17   15   18   19   27                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   12   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   17   28                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
11-Ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-4-yl acetic acid	Generator
11-Ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₉NO₆

Average Mass

449.5880 Da

Monoisotopic Mass

449.27774 Da

IUPAC Name

11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate

Traditional Name

11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CCN1CC2(C)CCC(OC)C34C2CC(C13)C1(O)CC(OC)C2CC4(O)C1C2OC(C)=O

InChI Identifier

InChI=1S/C25H39NO6/c1-6-26-12-22(3)8-7-18(31-5)25-17(22)9-15(21(25)26)23(28)11-16(30-4)14-10-24(25,29)20(23)19(14)32-13(2)27/h14-21,28-29H,6-12H2,1-5H3

InChI Key

NETXKASDOZAODV-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 variegatum	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
Quinolidine
Alkaloid or derivatives
Azepane
Piperidine
Cyclic alcohol
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Alcohol
Organopnictogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.28	ALOGPS
logP	-0.09	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	9.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	116.83 m³·mol⁻¹	ChemAxon
Polarizability	48.95 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

73804013

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-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate (NP0249049)

MOL for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D MOL for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D SDF for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D-SDF for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

PDB for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D PDB for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

SMILES for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

INCHI for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

Structure for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D Structure for NP0249049 (11-ethyl-2,8-dihydroxy-6,16-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)