NP-MRD: Showing NP-Card for (2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate (NP0242535)

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Record Information

Version

2.0

Created at

2022-09-07 02:52:27 UTC

Updated at

2022-09-07 02:52:27 UTC

NP-MRD ID

NP0242535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate

Description

Ptychantin H belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate is found in Ptychanthus striatus. Based on a literature review very few articles have been published on Ptychantin H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204522D          

 38 39  0  0  1  0            999 V2000
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  6 35  1  1  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072204522D          

 38 39  0  0  1  0            999 V2000
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    5.4187   -0.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707    0.0404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1637    0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6117   -0.4012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8666   -1.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4187   -1.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3146   -1.7989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  6  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 21 16  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
  6 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0242535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]12CC[C@@H](O)C(C)(C)[C@@H]1[C@@H](C[C@@](C)(OC(C)=O)[C@@H]2C[C@@H](OC(C)=O)[C@@](C)(O)C=C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O10/c1-10-26(8,34)23(37-18(4)31)13-21-27(9,38-19(5)32)14-20(36-17(3)30)24-25(6,7)22(33)11-12-28(21,24)15-35-16(2)29/h10,20-24,33-34H,1,11-15H2,2-9H3/t20-,21+,22-,23-,24+,26+,27-,28+/m1/s1

> <INCHI_KEY>
ZOLBTJUGZWGNAY-OJXKERJZSA-N

> <FORMULA>
C28H44O10

> <MOLECULAR_WEIGHT>
540.65

> <EXACT_MASS>
540.293447617

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.3298498701194

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-1-[(1R,2R,4R,4aR,6R,8aR)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-decahydronaphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate

> <JCHEM_LOGP>
1.1333151966666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.744097504156663

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.63601938038402

> <JCHEM_PKA_STRONGEST_BASIC>
-2.927654706138477

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
135.78949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-1-[(1R,2R,4R,4aR,6R,8aR)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1H-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-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       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.438   3.644   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.898   0.976   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.700   2.684   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.394   3.501   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.277   4.112   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.329   5.326   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.804   5.112   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.906   6.754   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.206   2.364   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.682   0.900   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.188   0.579   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.219   1.724   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.743   3.189   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      17.725   1.404   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.652  -0.245   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.128  -1.709   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.076  -2.923   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.487  -0.986   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.097  -2.854   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.573  -4.319   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.591  -2.534   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.115  -1.069   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.145   0.075   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.639   0.396   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.609  -0.749   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.084  -2.214   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.115  -3.358   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.054  -3.358   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   29                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   21    8   30                                             
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35    6   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄O₁₀

Average Mass

540.6500 Da

Monoisotopic Mass

540.29345 Da

IUPAC Name

(2R,3S)-1-[(1R,2R,4R,4aR,6R,8aR)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-decahydronaphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate

Traditional Name

(2R,3S)-1-[(1R,2R,4R,4aR,6R,8aR)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1H-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12CC[C@@H](O)C(C)(C)[C@@H]1[C@@H](C[C@@](C)(OC(C)=O)[C@@H]2C[C@@H](OC(C)=O)[C@@](C)(O)C=C)OC(C)=O

InChI Identifier

InChI=1S/C28H44O10/c1-10-26(8,34)23(37-18(4)31)13-21-27(9,38-19(5)32)14-20(36-17(3)30)24-25(6,7)22(33)11-12-28(21,24)15-35-16(2)29/h10,20-24,33-34H,1,11-15H2,2-9H3/t20-,21+,22-,23-,24+,26+,27-,28+/m1/s1

InChI Key

ZOLBTJUGZWGNAY-OJXKERJZSA-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
Ptychanthus striatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Labdane diterpenoid
Tetracarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.13	ChemAxon
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	135.79 m³·mol⁻¹	ChemAxon
Polarizability	56.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

15213237

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate (NP0242535)

MOL for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

3D MOL for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

3D SDF for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

3D-SDF for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

PDB for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

3D PDB for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

SMILES for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

INCHI for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

Structure for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)

3D Structure for NP0242535 ((2r,3s)-1-[(1r,2r,4r,4ar,6r,8ar)-2,4-bis(acetyloxy)-8a-[(acetyloxy)methyl]-6-hydroxy-2,5,5-trimethyl-hexahydro-1h-naphthalen-1-yl]-3-hydroxy-3-methylpent-4-en-2-yl acetate)