NP-MRD: Showing NP-Card for 14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one (NP0305340)

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Record Information

Version

2.0

Created at

2022-09-10 21:05:36 UTC

Updated at

2022-09-10 21:05:36 UTC

NP-MRD ID

NP0305340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one

Description

14-Ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]Docosan-21-one 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. 14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one is found in Delphinium elatum. 14-Ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]Docosan-21-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241514072D          

 31 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241514072D          

 31 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0305340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1CC2(C)CCC(OC)C34C5CC6C(O)C5C5(CC6OC)OCOC5(C13)C(=O)C24

> <INCHI_IDENTIFIER>
InChI=1S/C24H35NO6/c1-5-25-10-21(2)7-6-15(29-4)23-13-8-12-14(28-3)9-22(16(13)17(12)26)24(20(23)25,31-11-30-22)19(27)18(21)23/h12-18,20,26H,5-11H2,1-4H3

> <INCHI_KEY>
QUIBNSQWVBDPPR-UHFFFAOYSA-N

> <FORMULA>
C24H35NO6

> <MOLECULAR_WEIGHT>
433.545

> <EXACT_MASS>
433.246437851

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.482476127783755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.5258781903333316

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.778909325093416

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.479760835864475

> <JCHEM_PKA_STRONGEST_BASIC>
8.791228632873928

> <JCHEM_POLAR_SURFACE_AREA>
77.46000000000001

> <JCHEM_REFRACTIVITY>
110.66139999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one

> <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      -0.430  -4.366   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.106  -4.254   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.777  -2.869   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.923  -1.494   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.572  -0.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.129   0.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.049   1.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.561   1.954   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.524   0.742   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.029   1.070   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.498   2.537   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.129  -0.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.644  -0.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.013   0.960   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.586  -0.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.143  -1.838   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.984  -2.915   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.380  -2.712   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.029  -4.179   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.067  -5.359   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.658  -4.728   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.627  -3.110   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.545  -2.670   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.739  -2.355   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.243  -2.720   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.879  -0.688   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.540  -1.118   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.736   0.278   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.529   1.804   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.639  -2.200   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.702  -1.086   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   26                                             
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   23   26                                             
CONECT   13   12   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22   27                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   18   23   24                                             
CONECT   23   22    3   12                                                  
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    5   12                                                  
CONECT   27   18   13   28                                                  
CONECT   28   27   15   29                                                  
CONECT   29   28                                                            
CONECT   30   16   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₅NO₆

Average Mass

433.5450 Da

Monoisotopic Mass

433.24644 Da

IUPAC Name

14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one

Traditional Name

14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one

CAS Registry Number

Not Available

SMILES

CCN1CC2(C)CCC(OC)C34C5CC6C(O)C5C5(CC6OC)OCOC5(C13)C(=O)C24

InChI Identifier

InChI=1S/C24H35NO6/c1-5-25-10-21(2)7-6-15(29-4)23-13-8-12-14(28-3)9-22(16(13)17(12)26)24(20(23)25,31-11-30-22)19(27)18(21)23/h12-18,20,26H,5-11H2,1-4H3

InChI Key

QUIBNSQWVBDPPR-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
Delphinium elatum	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
Meta-dioxolane
Cyclic alcohol
Ketone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Acetal
Oxacycle
Dialkyl ether
Ether
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Hydrocarbon derivative
Organic oxide
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	0.89	ALOGPS
logP	0.53	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	110.66 m³·mol⁻¹	ChemAxon
Polarizability	46.48 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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 14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one (NP0305340)

MOL for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

3D MOL for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

3D SDF for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

3D-SDF for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

PDB for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

3D PDB for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

SMILES for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

INCHI for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

Structure for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)

3D Structure for NP0305340 (14-ethyl-4-hydroxy-6,19-dimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)