NP-MRD: Showing NP-Card for (3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate (NP0301617)

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Record Information

Version

2.0

Created at

2022-09-10 14:41:50 UTC

Updated at

2022-09-10 14:41:50 UTC

NP-MRD ID

NP0301617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate

Description

(24S)-24-Methyl-5alpha-cholestane-3beta,6beta,8beta,25-tetraol 25-acetate, also known as (24S)-24-methyl-5α-cholestane-3β,6β,8β,25-tetraol 25-acetic acid, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Based on a literature review very few articles have been published on (24S)-24-Methyl-5alpha-cholestane-3beta,6beta,8beta,25-tetraol 25-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102216412D          

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M  END

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M  END


  Mrv1652309102216412D          

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    4.1858   -3.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2146   -5.2103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 12  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 30 29  1  6  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
 17 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0301617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC[C@H](C)C(C)(C)OC(C)=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](O)C[C@@H]3[C@H](O)C[C@@]21O

> <INCHI_IDENTIFIER>
InChI=1S/C30H52O5/c1-18(8-9-19(2)27(4,5)35-20(3)31)22-10-11-25-28(22,6)15-13-26-29(7)14-12-21(32)16-23(29)24(33)17-30(25,26)34/h18-19,21-26,32-34H,8-17H2,1-7H3/t18-,19+,21+,22-,23-,24-,25-,26-,28-,29+,30-/m1/s1

> <INCHI_KEY>
MFWCHZGHVGCMLB-FPZSORRDSA-N

> <FORMULA>
C30H52O5

> <MOLECULAR_WEIGHT>
492.741

> <EXACT_MASS>
492.381474774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
59.25037169034503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,6R)-2,3-dimethyl-6-[(1R,2S,5S,7S,8R,10R,11R,14R,15R)-5,8,10-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptan-2-yl acetate

> <JCHEM_LOGP>
4.3125934956666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.858870543243238

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.104510671256975

> <JCHEM_PKA_STRONGEST_BASIC>
-2.690986497212517

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
138.30270000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6R)-2,3-dimethyl-6-[(1R,2S,5S,7S,8R,10R,11R,14R,15R)-5,8,10-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.576   0.559   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.631  -0.657   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.211  -2.084   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -5.105  -0.447   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.160  -1.662   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.376  -2.608   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.944  -0.717   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.215  -2.878   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.795  -4.305   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.690  -2.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.744  -3.883   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.362  -2.246   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.594  -3.453   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.867  -9.726   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.312  -7.735   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   34                                                  
CONECT   18   17   14   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   25   30                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   23   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   22   17   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(24S)-24-Methyl-5a-cholestane-3b,6b,8b,25-tetraol 25-acetate	Generator
(24S)-24-Methyl-5a-cholestane-3b,6b,8b,25-tetraol 25-acetic acid	Generator
(24S)-24-Methyl-5alpha-cholestane-3beta,6beta,8beta,25-tetraol 25-acetic acid	Generator
(24S)-24-Methyl-5α-cholestane-3β,6β,8β,25-tetraol 25-acetate	Generator
(24S)-24-Methyl-5α-cholestane-3β,6β,8β,25-tetraol 25-acetic acid	Generator

Chemical Formula

C₃₀H₅₂O₅

Average Mass

492.7410 Da

Monoisotopic Mass

492.38147 Da

IUPAC Name

(3S,6R)-2,3-dimethyl-6-[(1R,2S,5S,7S,8R,10R,11R,14R,15R)-5,8,10-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptan-2-yl acetate

Traditional Name

(3S,6R)-2,3-dimethyl-6-[(1R,2S,5S,7S,8R,10R,11R,14R,15R)-5,8,10-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptan-2-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](CC[C@H](C)C(C)(C)OC(C)=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](O)C[C@@H]3[C@H](O)C[C@@]21O

InChI Identifier

InChI=1S/C30H52O5/c1-18(8-9-19(2)27(4,5)35-20(3)31)22-10-11-25-28(22,6)15-13-26-29(7)14-12-21(32)16-23(29)24(33)17-30(25,26)34/h18-19,21-26,32-34H,8-17H2,1-7H3/t18-,19+,21+,22-,23-,24-,25-,26-,28-,29+,30-/m1/s1

InChI Key

MFWCHZGHVGCMLB-FPZSORRDSA-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 ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
Steroid ester
3-hydroxysteroid
3-beta-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	4.31	ChemAxon
pKa (Strongest Acidic)	14.1	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.3 m³·mol⁻¹	ChemAxon
Polarizability	59.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

27024858

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46855102

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate (NP0301617)

MOL for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

3D MOL for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

3D SDF for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

3D-SDF for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

PDB for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

3D PDB for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

SMILES for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

INCHI for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

Structure for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)

3D Structure for NP0301617 ((3s,6r)-6-[(1r,3ar,3br,5r,5as,7s,9as,9br,11ar)-3b,5,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-2-yl acetate)