NP-MRD: Showing NP-Card for 11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one (NP0160115)

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Record Information

Version

2.0

Created at

2022-09-02 17:59:56 UTC

Updated at

2022-09-02 17:59:56 UTC

NP-MRD ID

NP0160115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one

Description

11-Ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-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. 11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one is found in Delphinium biternatum. 11-Ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261505402D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004261505402D          

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M  END
> <DATABASE_ID>
NP0160115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1CC2(COC)C3C(OC)C4(O)C1C3(CCC2O)C1CC2C(CC4(O)C1C2=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H37NO7/c1-5-25-10-21(11-30-2)15(26)6-7-22-13-8-12-14(31-3)9-23(28,16(13)17(12)27)24(29,20(22)25)19(32-4)18(21)22/h12-16,18-20,26,28-29H,5-11H2,1-4H3

> <INCHI_KEY>
GBDXKPVZSMASOC-UHFFFAOYSA-N

> <FORMULA>
C24H37NO7

> <MOLECULAR_WEIGHT>
451.56

> <EXACT_MASS>
451.257002535

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.3286730927709

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one

> <ALOGPS_LOGP>
-0.78

> <JCHEM_LOGP>
-1.2859074550000011

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.735745356439232

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.171170511292166

> <JCHEM_PKA_STRONGEST_BASIC>
8.781886747810843

> <JCHEM_POLAR_SURFACE_AREA>
108.69000000000001

> <JCHEM_REFRACTIVITY>
114.63109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       0.868  -6.220   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.944  -4.599   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.770  -2.925   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.723  -1.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.397  -0.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.184   0.503   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.791   0.316   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.710   1.552   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.830   1.388   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.146   2.898   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.331   1.821   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.313   0.627   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.923  -0.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.383  -0.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.740   0.873   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.271  -0.446   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.787  -2.024   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.633  -3.120   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.113  -2.739   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.183  -4.369   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.266  -1.186   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.469   0.198   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.501   1.466   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.419  -3.175   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.573  -4.837   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.536  -2.541   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.863  -3.331   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.798  -3.509   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.704  -0.854   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.343  -2.804   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.424  -2.392   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.663  -1.313   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    9   29                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   29   30                                             
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   24                                             
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21   16   23                                                  
CONECT   23   22                                                            
CONECT   24   19   25   26   30                                             
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26    5   13                                                  
CONECT   30   24    3   13                                                  
CONECT   31   17   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₇NO₇

Average Mass

451.5600 Da

Monoisotopic Mass

451.25700 Da

IUPAC Name

11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one

Traditional Name

11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one

CAS Registry Number

Not Available

SMILES

CCN1CC2(COC)C3C(OC)C4(O)C1C3(CCC2O)C1CC2C(CC4(O)C1C2=O)OC

InChI Identifier

InChI=1S/C24H37NO7/c1-5-25-10-21(11-30-2)15(26)6-7-22-13-8-12-14(31-3)9-23(28,16(13)17(12)27)24(29,20(22)25)19(32-4)18(21)22/h12-16,18-20,26,28-29H,5-11H2,1-4H3

InChI Key

GBDXKPVZSMASOC-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 biternatum	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
1,2-aminoalcohol
Ketone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Polyol
Ether
Dialkyl ether
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Hydrocarbon derivative
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	-0.78	ALOGPS
logP	-1.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114.63 m³·mol⁻¹	ChemAxon
Polarizability	48.33 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

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-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one (NP0160115)

MOL for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D MOL for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D SDF for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D-SDF for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

PDB for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D PDB for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

SMILES for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

INCHI for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

Structure for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)

3D Structure for NP0160115 (11-ethyl-8,9,14-trihydroxy-6,18-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-one)