NP-MRD: Showing NP-Card for 15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one (NP0211304)

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Record Information

Version

1.0

Created at

2022-09-05 09:32:18 UTC

Updated at

2022-09-05 09:32:19 UTC

NP-MRD ID

NP0211304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one

Description

15-{7,7-Dimethyl-6-oxabicyclo[3.2.1]Octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-5-one belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. 15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one is found in Monocarpia marginalis. 15-{7,7-Dimethyl-6-oxabicyclo[3.2.1]Octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251509212D          

 34 40  0  0  0  0            999 V2000
    6.4248    5.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7919    4.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9899    4.3419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    3.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5966    3.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4432    4.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4535    3.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8149    2.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5850    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 18 19  1  0  0  0  0
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 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
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 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
 28 30  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004251509212D          

 34 40  0  0  0  0            999 V2000
    6.4248    5.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2CC1CCC2C1CCC2(C)C3CCC4C5(CC35CCC12C)CC(=O)C(O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O3/c1-26(2)23-9-10-24-29(6)12-11-20(19-8-7-18-15-22(19)34-27(18,3)4)28(29,5)13-14-30(24)17-31(23,30)16-21(32)25(26)33/h18-20,22-25,33H,7-17H2,1-6H3

> <INCHI_KEY>
YLLSLJJPDKOBCA-UHFFFAOYSA-N

> <FORMULA>
C31H48O3

> <MOLECULAR_WEIGHT>
468.722

> <EXACT_MASS>
468.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.46800082776395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
5.572747755666667

> <ALOGPS_LOGS>
-6.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.75969932306423

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.974867247629447

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6845916536799432

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
134.23519999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.86e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one

> <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      11.993   9.845   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.678   8.466   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.870   9.441   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.181   8.105   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.530   6.709   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.314   6.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.894   7.521   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.913   5.981   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.721   5.006   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.682   5.435   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   19   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   16   28   31                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   11   14   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₈O₃

Average Mass

468.7220 Da

Monoisotopic Mass

468.36035 Da

IUPAC Name

15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one

Traditional Name

15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2CC1CCC2C1CCC2(C)C3CCC4C5(CC35CCC12C)CC(=O)C(O)C4(C)C

InChI Identifier

InChI=1S/C31H48O3/c1-26(2)23-9-10-24-29(6)12-11-20(19-8-7-18-15-22(19)34-27(18,3)4)28(29,5)13-14-30(24)17-31(23,30)16-21(32)25(26)33/h18-20,22-25,33H,7-17H2,1-6H3

InChI Key

YLLSLJJPDKOBCA-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
Monocarpia marginalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
3-hydroxysteroid
Hydroxysteroid
Oxosteroid
2-oxosteroid
Oxepane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Cyclic ketone
Ketone
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
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	4.98	ALOGPS
logP	5.57	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.24 m³·mol⁻¹	ChemAxon
Polarizability	56.47 Å³	ChemAxon
Number of Rings	7	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

74348235

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one (NP0211304)

MOL for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

3D MOL for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

3D SDF for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

3D-SDF for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

PDB for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

3D PDB for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

SMILES for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

INCHI for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

Structure for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)

3D Structure for NP0211304 (15-{7,7-dimethyl-6-oxabicyclo[3.2.1]octan-4-yl}-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-5-one)