NP-MRD: Showing NP-Card for (1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate (NP0239394)

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Record Information

Version

2.0

Created at

2022-09-06 22:59:16 UTC

Updated at

2022-09-06 22:59:16 UTC

NP-MRD ID

NP0239394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate

Description

Caeruline 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,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate is found in Delphinium caeruleum. (1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate was first documented in 2021 (PMID: 34901611). Based on a literature review very few articles have been published on Caeruline.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072200592D          

 31 36  0  0  1  0            999 V2000
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    0.5804   -2.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484   -1.5670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -0.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0294    0.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801    0.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844    0.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106    0.3360    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.8839   -0.0973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6107    0.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310   -0.2387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.3050    1.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072200592D          

 31 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0239394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(C)C=C[C@H](O)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@@H]5[C@H](C[C@@H]6OC)[C@@H]([C@@H](OC(C)=O)[C@H]23)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C25H37NO5/c1-6-26-11-24(3)8-7-17(28)25-15-9-13-16(29-4)10-14(18(15)20(13)30-5)19(23(25)26)21(22(24)25)31-12(2)27/h7-8,13-23,28H,6,9-11H2,1-5H3/t13-,14+,15-,16+,17+,18-,19+,20+,21-,22-,23-,24+,25+/m1/s1

> <INCHI_KEY>
HXNWYLMLUMDOCL-JNLINPFGSA-N

> <FORMULA>
C25H37NO5

> <MOLECULAR_WEIGHT>
431.573

> <EXACT_MASS>
431.267173295

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.76331801556447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3R,4R,5R,6S,8S,9R,10R,13R,16S,17R,18S)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadec-14-en-18-yl acetate

> <JCHEM_LOGP>
0.6403366659999992

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.25917096265098

> <JCHEM_PKA_STRONGEST_BASIC>
9.849439034302325

> <JCHEM_POLAR_SURFACE_AREA>
68.23

> <JCHEM_REFRACTIVITY>
116.67840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4R,5R,6S,8S,9R,10R,13R,16S,17R,18S)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadec-14-en-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.532  -6.347   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.083  -4.761   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.770  -2.925   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.723  -1.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.397  -0.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.055   0.594   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830   1.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.331   1.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.313   0.627   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.532   1.554   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.923  -0.980   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.383  -0.182   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.740   0.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.271  -0.446   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.787  -2.024   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.333  -2.501   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.139  -3.870   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.633  -3.120   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.113  -2.739   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.419  -3.175   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.536  -2.541   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.168  -3.678   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.459  -3.624   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.273  -4.932   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.184  -2.266   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.704  -0.854   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.343  -2.804   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.266  -1.186   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.469   0.198   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.609   1.657   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.903   2.754   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   26                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   26   27                                             
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   11    5                                                  
CONECT   27   20    3   11                                                  
CONECT   28   19   12   29                                                  
CONECT   29   28   14   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₇NO₅

Average Mass

431.5730 Da

Monoisotopic Mass

431.26717 Da

IUPAC Name

(1S,2R,3R,4R,5R,6S,8S,9R,10R,13R,16S,17R,18S)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadec-14-en-18-yl acetate

Traditional Name

(1S,2R,3R,4R,5R,6S,8S,9R,10R,13R,16S,17R,18S)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadec-14-en-18-yl acetate

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(C)C=C[C@H](O)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@@H]5[C@H](C[C@@H]6OC)[C@@H]([C@@H](OC(C)=O)[C@H]23)[C@@H]14

InChI Identifier

InChI=1S/C25H37NO5/c1-6-26-11-24(3)8-7-17(28)25-15-9-13-16(29-4)10-14(18(15)20(13)30-5)19(23(25)26)21(22(24)25)31-12(2)27/h7-8,13-23,28H,6,9-11H2,1-5H3/t13-,14+,15-,16+,17+,18-,19+,20+,21-,22-,23-,24+,25+/m1/s1

InChI Key

HXNWYLMLUMDOCL-JNLINPFGSA-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 caeruleum	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
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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
logP	0.64	ChemAxon
pKa (Strongest Acidic)	14.26	ChemAxon
pKa (Strongest Basic)	9.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	116.68 m³·mol⁻¹	ChemAxon
Polarizability	47.76 Å³	ChemAxon
Number of Rings	6	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

101647997

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Alvarez-Caballero JM, Cuca-Suarez LE, Coy-Barrera E, Carrasco-Pancorbo A, Olmo-Garcia L, Martin J, Cruz M, Perez-Victoria I, Reyes F: Caerulines A and B, Flavonol Diacylglycosides from Persea caerulea. ACS Omega. 2021 Nov 23;6(48):32631-32636. doi: 10.1021/acsomega.1c04255. eCollection 2021 Dec 7. [PubMed:34901611 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate (NP0239394)

MOL for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

3D MOL for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

3D SDF for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

3D-SDF for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

PDB for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

3D PDB for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

SMILES for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

INCHI for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

Structure for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)

3D Structure for NP0239394 ((1s,2r,3r,4r,5r,6s,8s,9r,10r,13r,16s,17r,18s)-11-ethyl-16-hydroxy-4,6-dimethoxy-13-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-14-en-18-yl acetate)