NP-MRD: Showing NP-Card for 8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate (NP0300090)

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Record Information

Version

2.0

Created at

2022-09-10 12:17:50 UTC

Updated at

2022-09-10 12:17:51 UTC

NP-MRD ID

NP0300090

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate

Description

5'-(Acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]Nonadecan]-14'-en-8'-yl acetate belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. 8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate is found in Eurycoma longifolia. 5'-(Acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]Nonadecan]-14'-en-8'-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251509332D          

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M  END

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M  END


  Mrv1533004251509332D          

 36 41  0  0  0  0            999 V2000
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 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 12 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300090

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(=O)OC2CC3C(C)=CC(=O)C(O)C3(C)C3C4(O)OCC23C1(O)C1(CO1)C4OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O12/c1-9-5-13(27)15(28)20(4)12(9)6-14-21-7-33-23(30,18(20)21)19(35-11(3)26)22(8-32-22)24(21,31)16(17(29)36-14)34-10(2)25/h5,12,14-16,18-19,28,30-31H,6-8H2,1-4H3

> <INCHI_KEY>
WTCMEJJWMIBEMX-UHFFFAOYSA-N

> <FORMULA>
C24H28O12

> <MOLECULAR_WEIGHT>
508.476

> <EXACT_MASS>
508.158076342

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.22619107782066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-8'-yl acetate

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-1.5525690216666663

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.885074253536919

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.731577954902487

> <JCHEM_PKA_STRONGEST_BASIC>
-3.701560011707792

> <JCHEM_POLAR_SURFACE_AREA>
178.42000000000002

> <JCHEM_REFRACTIVITY>
113.2251

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-8'-yl acetate

> <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       9.465  -9.223   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.209  -7.875   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.749  -7.845   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.414  -6.556   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.874  -6.586   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.121  -7.919   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.879  -9.260   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.587  -7.877   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.858  -6.493   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.326  -6.680   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.399  -5.452   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.865  -5.583   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.017  -4.321   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.636  -2.926   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.245  -1.663   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.171  -2.794   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.824  -1.399   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.052  -4.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.773  -2.696   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.766  -4.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.878  -2.642   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.229  -1.142   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.560  -2.001   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.024  -3.485   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.431  -4.984   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.060  -5.265   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.597  -5.355   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.010  -4.065   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.438  -3.488   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.224  -5.013   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.443  -2.654   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.311  -1.381   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.846  -1.496   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.714  -0.224   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.515  -2.884   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.212  -6.978   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   26                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22   23   31                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    9   20   26                                             
CONECT   26   25    5   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
CONECT   31   28   21   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   12                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Value	Source
5'-(Acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0,.0,.0,]nonadecan]-14'-en-8'-yl acetic acid	Generator
5'-(Acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-8'-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₈O₁₂

Average Mass

508.4760 Da

Monoisotopic Mass

508.15808 Da

IUPAC Name

5'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-8'-yl acetate

Traditional Name

5'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-8'-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(=O)OC2CC3C(C)=CC(=O)C(O)C3(C)C3C4(O)OCC23C1(O)C1(CO1)C4OC(C)=O

InChI Identifier

InChI=1S/C24H28O12/c1-9-5-13(27)15(28)20(4)12(9)6-14-21-7-33-23(30,18(20)21)19(35-11(3)26)22(8-32-22)24(21,31)16(17(29)36-14)34-10(2)25/h5,12,14-16,18-19,28,30-31H,6-8H2,1-4H3

InChI Key

WTCMEJJWMIBEMX-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
Eurycoma longifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Cyclohexenone
Oxepane
Oxane
Pyran
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Cyclic ketone
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Oxacycle
Carbonyl group
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	-0.12	ALOGPS
logP	-1.6	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.73	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	178.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.23 m³·mol⁻¹	ChemAxon
Polarizability	48.23 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate (NP0300090)

MOL for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

3D MOL for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

3D SDF for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

3D-SDF for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

PDB for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

3D PDB for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

SMILES for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

INCHI for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

Structure for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)

3D Structure for NP0300090 (8'-(acetyloxy)-4',7',17'-trihydroxy-14',18'-dimethyl-9',16'-dioxo-3',10'-dioxaspiro[oxirane-2,6'-pentacyclo[9.8.0.0¹,⁷.0⁴,¹⁹.0¹³,¹⁸]nonadecan]-14'-en-5'-yl acetate)