NP-MRD: Showing NP-Card for Episcopalidine (NP0067179)

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Record Information

Version

2.0

Created at

2022-04-28 11:27:06 UTC

Updated at

2022-04-28 11:27:07 UTC

NP-MRD ID

NP0067179

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Episcopalidine

Description

(1S,3R,4R,5S,8S,9R,11R,14S,17R,18S)-3-(acetyloxy)-5,7-dimethyl-12-methylidene-10,16-dioxo-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-4-yl benzoate belongs to the class of organic compounds known as hetidine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetidine skeleton, which is a hexacyclic compound with an additional C-20-C-14 bond in the atisine-type. Episcopalidine is found in Aconitum contortum and Aconitum episcopale. Based on a literature review very few articles have been published on (1S,3R,4R,5S,8S,9R,11R,14S,17R,18S)-3-(acetyloxy)-5,7-dimethyl-12-methylidene-10,16-dioxo-7-azahexacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-4-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213272D          

 37 43  0  0  1  0            999 V2000
    2.8586    2.0344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282213272D          

 37 43  0  0  1  0            999 V2000
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 14 13  1  6  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  6  0  0  0
  1 16  1  0  0  0  0
 14 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 18 20  1  0  0  0  0
 12 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 11 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 10 34  1  1  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
  1 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0067179

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@@]2(C)[C@@H](OC(=O)C3=CC=CC=C3)[C@@H](C[C@]34[C@H]5C[C@@H]6C(=C)C[C@@]5(CC(=O)[C@@H]23)[C@H]([C@H]14)C6=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H33NO6/c1-15-11-29-12-19(33)24-28(3)14-31(4)25-22(29)23(34)18(15)10-21(29)30(24,25)13-20(36-16(2)32)26(28)37-27(35)17-8-6-5-7-9-17/h5-9,18,20-22,24-26H,1,10-14H2,2-4H3/t18-,20-,21+,22+,24+,25+,26+,28-,29+,30+/m1/s1

> <INCHI_KEY>
PZNXWOJHEGLWBY-BTIIQKHQSA-N

> <FORMULA>
C30H33NO6

> <MOLECULAR_WEIGHT>
503.595

> <EXACT_MASS>
503.230787787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.23611210723013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4R,5S,8S,9R,11R,14S,17R,18S)-3-(acetyloxy)-5,7-dimethyl-12-methylidene-10,16-dioxo-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecan-4-yl benzoate

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.906688213666666

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.157501549884227

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.36845130173337

> <JCHEM_PKA_STRONGEST_BASIC>
8.667799353742542

> <JCHEM_POLAR_SURFACE_AREA>
89.97999999999999

> <JCHEM_REFRACTIVITY>
133.6045

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,5S,8S,9R,11R,14S,17R,18S)-3-(acetyloxy)-5,7-dimethyl-12-methylidene-10,16-dioxo-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecan-4-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.336   3.797   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.265   4.896   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.659   6.384   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.798   4.474   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.640   2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.129   1.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.478   0.891   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.253  -0.465   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.334   2.342   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.757   3.654   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.475   2.396   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.531   4.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.592   4.312   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.794   3.199   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.641   2.088   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.405   2.460   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.270   4.643   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.087   5.695   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -1.424   5.261   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.429   7.197   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.708   5.043   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.156   4.520   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.428   3.005   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.333   5.514   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.844   0.901   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.323   0.474   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.433   1.541   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.693  -1.021   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.583  -2.089   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.952  -3.584   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.432  -4.011   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.542  -2.944   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.172  -1.449   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.317   3.109   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.877   1.681   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.429   2.262   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.720   1.423   0.000  0.00  0.00           C+0
CONECT    1    2   16   36                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   17                                                  
CONECT    5    4    6   15   35                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11   19   34                                             
CONECT   11   10   12   25                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15   17                                             
CONECT   15   14    5   16                                                  
CONECT   16   15    1                                                       
CONECT   17   14    4   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   10                                                       
CONECT   20   18                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   11   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   10                                                            
CONECT   35    5   36                                                       
CONECT   36   35    1   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1S,3R,4R,5S,8S,9R,11R,14S,17R,18S)-3-(Acetyloxy)-5,7-dimethyl-12-methylidene-10,16-dioxo-7-azahexacyclo[9.6.2.0,.0,.0,.0,]nonadecan-4-yl benzoic acid	Generator

Chemical Formula

C₃₀H₃₃NO₆

Average Mass

503.5950 Da

Monoisotopic Mass

503.23079 Da

IUPAC Name

(1S,3R,4R,5S,8S,9R,11R,14S,17R,18S)-3-(acetyloxy)-5,7-dimethyl-12-methylidene-10,16-dioxo-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecan-4-yl benzoate

Traditional Name

(1S,3R,4R,5S,8S,9R,11R,14S,17R,18S)-3-(acetyloxy)-5,7-dimethyl-12-methylidene-10,16-dioxo-7-azahexacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{9,14}.0^{14,18}]nonadecan-4-yl benzoate

CAS Registry Number

Not Available

SMILES

CN1C[C@@]2(C)[C@@H](OC(=O)C3=CC=CC=C3)[C@@H](C[C@]34[C@H]5C[C@@H]6C(=C)C[C@@]5(CC(=O)[C@@H]23)[C@H]([C@H]14)C6=O)OC(C)=O

InChI Identifier

InChI=1S/C30H33NO6/c1-15-11-29-12-19(33)24-28(3)14-31(4)25-22(29)23(34)18(15)10-21(29)30(24,25)13-20(36-16(2)32)26(28)37-27(35)17-8-6-5-7-9-17/h5-9,18,20-22,24-26H,1,10-14H2,2-4H3/t18-,20-,21+,22+,24+,25+,26+,28-,29+,30+/m1/s1

InChI Key

PZNXWOJHEGLWBY-BTIIQKHQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 contortum	Plant	KNApSAcK
Aconitum episcopale	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hetidine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetidine skeleton, which is a hexacyclic compound with an additional C-20-C-14 bond in the atisine-type.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Hetidine-type diterpenoid alkaloids

Alternative Parents

Substituents

Hetidine-type diterpenoid alkaloid
Benzoate ester
Alkaloid or derivatives
Benzoic acid or derivatives
Benzoyl
Benzenoid
Piperidine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Ketone
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.22	ALOGPS
logP	2.91	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	16.37	ChemAxon
pKa (Strongest Basic)	8.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.6 m³·mol⁻¹	ChemAxon
Polarizability	53.24 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162975416

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Episcopalidine (NP0067179)

MOL for NP0067179 (Episcopalidine)

3D MOL for NP0067179 (Episcopalidine)

3D SDF for NP0067179 (Episcopalidine)

3D-SDF for NP0067179 (Episcopalidine)

PDB for NP0067179 (Episcopalidine)

3D PDB for NP0067179 (Episcopalidine)

SMILES for NP0067179 (Episcopalidine)

INCHI for NP0067179 (Episcopalidine)

Structure for NP0067179 (Episcopalidine)

3D Structure for NP0067179 (Episcopalidine)