NP-MRD: Showing NP-Card for (1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one (NP0297665)

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Record Information

Version

2.0

Created at

2022-09-10 08:13:03 UTC

Updated at

2022-09-10 08:13:03 UTC

NP-MRD ID

NP0297665

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one

Description

PACININE 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. (1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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. Based on a literature review very few articles have been published on PACININE.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102210132D          

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M  END

     RDKit          2D

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M  END


  Mrv1652309102210132D          

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M  END
> <DATABASE_ID>
NP0297665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C)CC[C@H](OC)[C@]34[C@@H]5C[C@H]6[C@H](OC)[C@@H]5[C@@]5(C[C@@H]6OC)OCO[C@]5([C@@H]13)C(=O)[C@H]24

> <INCHI_IDENTIFIER>
InChI=1S/C25H37NO6/c1-6-26-11-22(2)8-7-16(29-4)24-14-9-13-15(28-3)10-23(17(14)18(13)30-5)25(21(24)26,32-12-31-23)20(27)19(22)24/h13-19,21H,6-12H2,1-5H3/t13-,14-,15+,16+,17-,18+,19-,21+,22+,23-,24+,25+/m1/s1

> <INCHI_KEY>
FTEXZAOPVCNOHP-NXHWWDTFSA-N

> <FORMULA>
C25H37NO6

> <MOLECULAR_WEIGHT>
447.572

> <EXACT_MASS>
447.262087915

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.705   1.499   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.169   1.388   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.497   0.002   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.352  -1.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.702  -2.847   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.145  -3.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.225  -4.396   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.287  -4.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.250  -3.609   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.755  -3.937   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.223  -5.404   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.854  -2.007   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.271  -0.197   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.352   0.243   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.384   1.861   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.792   2.492   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.755   1.312   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.106  -0.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.709   0.048   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.868  -1.029   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.365  -0.667   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.799   0.811   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.312  -2.572   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.738  -3.827   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.370  -2.759   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.265  -1.749   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.462  -3.145   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.255  -4.671   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.473  -5.613   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.465  -0.512   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.031  -0.147   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.605  -2.179   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   32                                             
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   25   32                                             
CONECT   13   12    3   14                                                  
CONECT   14   13   15   18   30                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19   26                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   12   26                                                  
CONECT   26   25   18   27                                                  
CONECT   27   26   23   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   14   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   12    5                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₇NO₆

Average Mass

447.5720 Da

Monoisotopic Mass

447.26209 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(C)CC[C@H](OC)[C@]34[C@@H]5C[C@H]6[C@H](OC)[C@@H]5[C@@]5(C[C@@H]6OC)OCO[C@]5([C@@H]13)C(=O)[C@H]24

InChI Identifier

InChI=1S/C25H37NO6/c1-6-26-11-22(2)8-7-16(29-4)24-14-9-13-15(28-3)10-23(17(14)18(13)30-5)25(21(24)26,32-12-31-23)20(27)19(22)24/h13-19,21H,6-12H2,1-5H3/t13-,14-,15+,16+,17-,18+,19-,21+,22+,23-,24+,25+/m1/s1

InChI Key

FTEXZAOPVCNOHP-NXHWWDTFSA-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
Ketone
Tertiary amine
Tertiary aliphatic amine
Acetal
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organopnictogen compound
Aldehyde
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Amine
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

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

28489416

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57392358

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one (NP0297665)

MOL for NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-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 NP0297665 ((1s,2r,3r,4s,5r,6s,8r,12s,13s,16r,19s,20r)-14-ethyl-4,6,19-trimethoxy-16-methyl-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosan-21-one)