NP-MRD: Showing NP-Card for [(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate (NP0146405)

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Record Information

Version

2.0

Created at

2022-09-02 01:47:57 UTC

Updated at

2022-09-02 01:47:57 UTC

NP-MRD ID

NP0146405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate

Description

18-Benzoyldavisinol 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. [(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate was first documented in 2021 (PMID: 34240855). Based on a literature review very few articles have been published on 18-Benzoyldavisinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203472D          

 31 38  0  0  1  0            999 V2000
   -1.1906    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2644    0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    0.6350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9611    1.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940    0.6205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4176   -0.0472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0434   -0.6807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4083   -1.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2315   -1.4746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6899   -0.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250   -0.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5131   -0.8426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1596   -0.9505    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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   -1.4343   -1.1013    0.3512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8281   -1.3423   -0.2494 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022203472D          

 31 38  0  0  1  0            999 V2000
   -1.1906    0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845    0.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1203    0.6350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0146405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H]2[C@@]34C[C@H]5[C@@H]6[C@]7(COC(=O)C8=CC=CC=C8)CN5[C@H]([C@H]3C[C@@H]1C(=C)C4)[C@]26CCC7

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO3/c1-15-11-26-12-19-21-25(14-31-24(30)16-6-3-2-4-7-16)8-5-9-27(21)22(26)20(29)17(15)10-18(26)23(27)28(19)13-25/h2-4,6-7,17-23,29H,1,5,8-14H2/t17-,18-,19+,20+,21-,22-,23-,25+,26+,27+/m1/s1

> <INCHI_KEY>
LWCZLKLWGRYTGX-RAAJJMTLSA-N

> <FORMULA>
C27H31NO3

> <MOLECULAR_WEIGHT>
417.549

> <EXACT_MASS>
417.230393862

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.14779663490701

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,5S,8R,9S,11R,14S,16S,17S,18R,19S)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-5-yl]methyl benzoate

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
2.982087700000001

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.589082972208196

> <JCHEM_PKA_STRONGEST_BASIC>
9.399054713794012

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
116.9139

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,5S,8R,9S,11R,14S,16S,17S,18R,19S)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-5-yl]methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.223   0.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.718   0.568   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.494   1.597   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.091   1.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.661   1.913   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.216   1.158   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.379  -0.088   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.548  -1.271   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.229  -2.652   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.766  -2.753   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.621  -1.472   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.940  -0.091   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.158  -1.573   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.013  -0.292   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.550  -0.393   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.231  -1.774   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.376  -3.055   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.839  -2.954   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.002  -0.619   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.131   0.747   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.497   1.091   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.803   0.273   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.900  -1.136   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.395  -0.629   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.202  -1.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.056  -0.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.370  -0.066   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.309   1.473   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.138   0.309   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       5.329  -0.655   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       6.161  -2.019   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24   29                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8   22                                                  
CONECT    8    7    9   19   31                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    8   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    7   23   29                                             
CONECT   23   22   24   30                                                  
CONECT   24   23    4   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    2   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    4   22                                                  
CONECT   30   23    6   31                                                  
CONECT   31   30    8                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   76    0
END

View in JSmol

Synonyms

Value	Source
18-Benzoyl-davisinol	MeSH

Chemical Formula

C₂₇H₃₁NO₃

Average Mass

417.5490 Da

Monoisotopic Mass

417.23039 Da

IUPAC Name

[(1S,5S,8R,9S,11R,14S,16S,17S,18R,19S)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-5-yl]methyl benzoate

Traditional Name

[(1S,5S,8R,9S,11R,14S,16S,17S,18R,19S)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-5-yl]methyl benzoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H]2[C@@]34C[C@H]5[C@@H]6[C@]7(COC(=O)C8=CC=CC=C8)CN5[C@H]([C@H]3C[C@@H]1C(=C)C4)[C@]26CCC7

InChI Identifier

InChI=1S/C27H31NO3/c1-15-11-26-12-19-21-25(14-31-24(30)16-6-3-2-4-7-16)8-5-9-27(21)22(26)20(29)17(15)10-18(26)23(27)28(19)13-25/h2-4,6-7,17-23,29H,1,5,8-14H2/t17-,18-,19+,20+,21-,22-,23-,25+,26+,27+/m1/s1

InChI Key

LWCZLKLWGRYTGX-RAAJJMTLSA-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

Not Available

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
Quinolizidine
Benzoate ester
Azaspirodecane
Alkaloid or derivatives
Isoindole or derivatives
Isoindoline
Indolizidine
Indole or derivatives
Benzoic acid or derivatives
Benzoyl
Azepane
Benzenoid
N-alkylpyrrolidine
Piperidine
Monocyclic benzene moiety
Pyrrolidine
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
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	ALOGPS
logP	2.98	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	9.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.91 m³·mol⁻¹	ChemAxon
Polarizability	43.15 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

C00024819

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

101714438

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yu K, Yao F, Zeng Q, Xie H, Ding H: Asymmetric Total Syntheses of (+)-Davisinol and (+)-18-Benzoyldavisinol: A HAT-Initiated Transannular Redox Radical Approach. J Am Chem Soc. 2021 Jul 21;143(28):10576-10581. doi: 10.1021/jacs.1c05703. Epub 2021 Jul 9. [PubMed:34240855 ]
LOTUS database [Link]

Showing NP-Card for [(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate (NP0146405)

MOL for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

3D MOL for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

3D SDF for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

3D-SDF for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

PDB for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

3D PDB for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

SMILES for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

INCHI for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

Structure for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)

3D Structure for NP0146405 ([(1s,5s,8r,9s,11r,14s,16s,17s,18r,19s)-19-hydroxy-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-5-yl]methyl benzoate)