NP-MRD: Showing NP-Card for (1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate (NP0243383)

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Record Information

Version

2.0

Created at

2022-09-07 03:55:11 UTC

Updated at

2022-09-07 03:55:11 UTC

NP-MRD ID

NP0243383

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate

Description

12-Acetyllucidusculine belongs to the class of organic compounds known as napelline-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the napelline skeleton, which is a hexacyclic compound, with an additional C-20-C-7 bond in the kaurane-type. (1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate is found in Aconitum flavum and Aconitum sachalinense. Based on a literature review very few articles have been published on 12-acetyllucidusculine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072205552D          

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M  END

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  Mrv1652309072205552D          

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M  END
> <DATABASE_ID>
NP0243383

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C)CC[C@@H](O)[C@@]34[C@@H]2CC(C13)[C@@]12C[C@H]([C@H](C[C@@H]41)OC(C)=O)C(=C)[C@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H37NO5/c1-6-27-12-24(5)8-7-21(30)26-19(24)9-17(22(26)27)25-11-16(13(2)23(25)32-15(4)29)18(10-20(25)26)31-14(3)28/h16-23,30H,2,6-12H2,1,3-5H3/t16-,17?,18-,19+,20+,21+,22?,23+,24-,25-,26-/m0/s1

> <INCHI_KEY>
LBTGOQKCUJMQQK-RFXPKWRHSA-N

> <FORMULA>
C26H37NO5

> <MOLECULAR_WEIGHT>
443.584

> <EXACT_MASS>
443.267173295

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
46.52782429402319

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,5S,7R,8R,13R,16R,17R)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-7-yl acetate

> <JCHEM_LOGP>
1.4131371076666661

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.635443242438757

> <JCHEM_PKA_STRONGEST_BASIC>
10.217904168735304

> <JCHEM_POLAR_SURFACE_AREA>
76.07

> <JCHEM_REFRACTIVITY>
117.99159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5S,7R,8R,13R,16R,17R)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1^{5,8}.0^{1,10}.0^{2,8}.0^{13,17}]nonadecan-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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       9.013   1.623   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.648   2.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.428   3.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.275   3.469   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.010   2.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.918   1.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.086   0.364   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.912   1.344   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.453   1.088   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.519  -0.023   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.601   2.650   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.150   4.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.364   4.416   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.835   5.883   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.432   3.290   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.326   2.388   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.665   3.071   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.312   4.570   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.162   5.014   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.472   1.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.060   4.025   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.909   5.417   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.549   5.385   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.307   6.726   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.847   6.740   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.605   8.081   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.629   5.413   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.204   1.594   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.993   0.069   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.209  -0.877   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.635  -0.297   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.997  -2.402   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21   28                                             
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11   20                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8   16   21                                             
CONECT   16   15    6   17                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17    9                                                       
CONECT   21   15    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    5    2   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

Not Available

Chemical Formula

C₂₆H₃₇NO₅

Average Mass

443.5840 Da

Monoisotopic Mass

443.26717 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(C)CC[C@@H](O)[C@@]34[C@@H]2CC(C13)[C@@]12C[C@H]([C@H](C[C@@H]41)OC(C)=O)C(=C)[C@H]2OC(C)=O

InChI Identifier

InChI=1S/C26H37NO5/c1-6-27-12-24(5)8-7-21(30)26-19(24)9-17(22(26)27)25-11-16(13(2)23(25)32-15(4)29)18(10-20(25)26)31-14(3)28/h16-23,30H,2,6-12H2,1,3-5H3/t16-,17?,18-,19+,20+,21+,22?,23+,24-,25-,26-/m0/s1

InChI Key

LBTGOQKCUJMQQK-RFXPKWRHSA-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 flavum	LOTUS Database	35616633
Aconitum sachalinense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as napelline-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the napelline skeleton, which is a hexacyclic compound, with an additional C-20-C-7 bond in the kaurane-type.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Napelline-type diterpenoid alkaloids

Alternative Parents

Substituents

Napelline-type diterpenoid alkaloid
Alkaloid or derivatives
Azepane
Dicarboxylic acid or derivatives
Piperidine
Cyclic alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxide
Organonitrogen compound
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Amine
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038133

Chemspider ID

23311471

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44445647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate (NP0243383)

MOL for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

3D MOL for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

3D SDF for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

3D-SDF for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

PDB for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

3D PDB for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

SMILES for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

INCHI for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

Structure for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)

3D Structure for NP0243383 ((1r,2r,4s,5s,7r,8r,13r,16r,17r)-4-(acetyloxy)-11-ethyl-16-hydroxy-13-methyl-6-methylidene-11-azahexacyclo[7.7.2.1⁵,⁸.0¹,¹⁰.0²,⁸.0¹³,¹⁷]nonadecan-7-yl acetate)