NP-MRD: Showing NP-Card for 2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate (NP0217054)

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Record Information

Version

2.0

Created at

2022-09-05 17:16:04 UTC

Updated at

2022-09-05 17:16:04 UTC

NP-MRD ID

NP0217054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate

Description

2-(Acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl benzoate belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class. 2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate is found in Aconitum sanyoense. 2-(Acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl benzoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251510532D          

 36 43  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004251510532D          

 36 43  0  0  0  0            999 V2000
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 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 15 22  1  0  0  0  0
 21 23  1  0  0  0  0
  8 23  1  0  0  0  0
 12 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217054

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(CC2(C)CN3C4CC56C7CC(CC5(O)C1(C37)C24)C(=C)C6O)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H33NO6/c1-14-17-9-18-22-29-21-19(11-27(18,23(14)32)28(29,34)10-17)30(22)13-26(21,3)12-20(24(29)35-15(2)31)36-25(33)16-7-5-4-6-8-16/h4-8,17-24,32,34H,1,9-13H2,2-3H3

> <INCHI_KEY>
UHHNHGRRAVEXIE-UHFFFAOYSA-N

> <FORMULA>
C29H33NO6

> <MOLECULAR_WEIGHT>
491.584

> <EXACT_MASS>
491.230787787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.747199397819436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
1.550784748000002

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.326869210224853

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.584434699906108

> <JCHEM_PKA_STRONGEST_BASIC>
8.937071365005412

> <JCHEM_POLAR_SURFACE_AREA>
96.30000000000001

> <JCHEM_REFRACTIVITY>
128.3878

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       9.371   6.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.891   7.284   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.518   8.778   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.783   6.214   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.156   4.720   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.661   4.254   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.989   2.719   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.758   1.794   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.179   0.367   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.505   3.405   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.055   4.196   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.322   2.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.218   1.469   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.090   2.415   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.224   4.267   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.744   4.794   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.737   3.687   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.021   2.527   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.061   2.773   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.876   1.466   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.940   3.495   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.759   4.659   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.350   1.829   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.461   2.212   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.939   1.568   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.805   1.435   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.903  -0.102   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.798   5.292   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.266   4.827   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.403   5.866   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.597   3.323   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.065   2.858   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.396   1.354   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.259   0.315   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.791   0.780   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.460   2.284   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   23                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19   26                                             
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    5   22   23                                             
CONECT   22   21   11   15                                                  
CONECT   23   21    8   12                                                  
CONECT   24   17   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   14   27                                                  
CONECT   27   26                                                            
CONECT   28    6   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   86    0
END

View in JSmol

Synonyms

Value	Source
2-(Acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-3-yl benzoic acid	Generator
2-(Acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoic acid	Generator

Chemical Formula

C₂₉H₃₃NO₆

Average Mass

491.5840 Da

Monoisotopic Mass

491.23079 Da

IUPAC Name

2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate

Traditional Name

2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(CC2(C)CN3C4CC56C7CC(CC5(O)C1(C37)C24)C(=C)C6O)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H33NO6/c1-14-17-9-18-22-29-21-19(11-27(18,23(14)32)28(29,34)10-17)30(22)13-26(21,3)12-20(24(29)35-15(2)31)36-25(33)16-7-5-4-6-8-16/h4-8,17-24,32,34H,1,9-13H2,2-3H3

InChI Key

UHHNHGRRAVEXIE-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
Aconitum sanyoense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hetisine-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hetisine skeleton, which is a heptacyclic compound with an additional N-C-6 bond as compared with the hetidine-type, and thus, is one of most complex entries in the atisane-class.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Hetisine-type diterpenoid alkaloids

Alternative Parents

Substituents

Hetisine-type diterpenoid alkaloid
Azaspirodecane
Benzoate ester
Quinolizidine
Benzoic acid or derivatives
Indole or derivatives
Alkaloid or derivatives
Indolizidine
Isoindoline
Isoindole or derivatives
Benzoyl
Azepane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
N-alkylpyrrolidine
Piperidine
Tertiary alcohol
Pyrrolidine
Cyclic alcohol
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
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	1.27	ALOGPS
logP	1.55	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	8.94	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	128.39 m³·mol⁻¹	ChemAxon
Polarizability	51.75 Å³	ChemAxon
Number of Rings	8	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

85082556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate (NP0217054)

MOL for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

3D MOL for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

3D SDF for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

3D-SDF for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

PDB for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

3D PDB for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

SMILES for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

INCHI for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

Structure for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)

3D Structure for NP0217054 (2-(acetyloxy)-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)