NP-MRD: Showing NP-Card for 13,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate (NP0214483)

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Record Information

Version

2.0

Created at

2022-09-05 13:47:29 UTC

Updated at

2022-09-05 13:47:29 UTC

NP-MRD ID

NP0214483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13,19-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

13,19-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. 13,19-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 japonicum. 13,19-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


  Mrv1533004241521122D          

 32 39  0  0  0  0            999 V2000
    5.9678    0.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1752    1.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4820    1.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7606    1.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444   -0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1510   -0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004241521122D          

 32 39  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0214483

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CN3C4CC56C7CC(C(O)C5C(CC(C1)OC(=O)C1=CC=CC=C1)(C37)C24)C(=C)C6O

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO4/c1-13-16-8-17-22-27-10-15(32-24(31)14-6-4-3-5-7-14)9-25(2)12-28(22)18(20(25)27)11-26(17,23(13)30)21(27)19(16)29/h3-7,15-23,29-30H,1,8-12H2,2H3

> <INCHI_KEY>
AHJYUWVTHMSHBB-UHFFFAOYSA-N

> <FORMULA>
C27H31NO4

> <MOLECULAR_WEIGHT>
433.548

> <EXACT_MASS>
433.225308482

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.14227824565095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,19-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>
1.58

> <JCHEM_LOGP>
1.8012367226666666

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.721911324532705

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.992105378334948

> <JCHEM_PKA_STRONGEST_BASIC>
9.156789500907504

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
118.17019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,19-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                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      11.140   0.514   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.600   0.543   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.660   2.067   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.366   2.911   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.020   2.287   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.966   0.696   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.110  -0.370   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.749  -1.371   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.338  -2.108   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.239  -0.916   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.300   0.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.791   1.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.536   0.072   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.976   1.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.740   0.219   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.344   1.272   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.253   0.558   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       9.602  -0.867   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.651  -1.431   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.422  -2.359   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.057  -1.950   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.336  -3.464   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.436   3.019   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.477   4.447   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.202   5.311   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.817   4.639   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.313   6.847   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.039   7.712   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.149   9.248   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.535   9.919   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.810   9.055   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.699   7.519   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11   16                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15   21                                             
CONECT   11   10    6   12                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    6   17                                                  
CONECT   17   16    8   18                                                  
CONECT   18   17    2                                                       
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   10   22                                                  
CONECT   22   21                                                            
CONECT   23   12                                                            
CONECT   24    4   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   78    0
END

View in JSmol

Synonyms

Value	Source
13,19-Dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-3-yl benzoic acid	Generator
13,19-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

C₂₇H₃₁NO₄

Average Mass

433.5480 Da

Monoisotopic Mass

433.22531 Da

IUPAC Name

13,19-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

13,19-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

CC12CN3C4CC56C7CC(C(O)C5C(CC(C1)OC(=O)C1=CC=CC=C1)(C37)C24)C(=C)C6O

InChI Identifier

InChI=1S/C27H31NO4/c1-13-16-8-17-22-27-10-15(32-24(31)14-6-4-3-5-7-14)9-25(2)12-28(22)18(20(25)27)11-26(17,23(13)30)21(27)19(16)29/h3-7,15-23,29-30H,1,8-12H2,2H3

InChI Key

AHJYUWVTHMSHBB-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 japonicum	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
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Cyclic alcohol
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Amine
Organonitrogen compound
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	1.58	ALOGPS
logP	1.8	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.99	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	118.17 m³·mol⁻¹	ChemAxon
Polarizability	47.14 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

78299355

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate (NP0214483)

MOL for NP0214483 (13,19-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 NP0214483 (13,19-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 NP0214483 (13,19-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 NP0214483 (13,19-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 NP0214483 (13,19-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 NP0214483 (13,19-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 NP0214483 (13,19-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 NP0214483 (13,19-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 NP0214483 (13,19-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 NP0214483 (13,19-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl benzoate)