NP-MRD: Showing NP-Card for (2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one (NP0182789)

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Record Information

Version

2.0

Created at

2022-09-03 21:34:58 UTC

Updated at

2022-09-03 21:34:58 UTC

NP-MRD ID

NP0182789

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one

Description

Abiesatrine A belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Based on a literature review very few articles have been published on Abiesatrine A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223342D          

 34 39  0  0  1  0            999 V2000
    1.9639   -1.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905   -0.9573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.8788    1.5514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2796    2.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6695    1.7868    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1328    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0236    2.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0  0  0  0
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 33 34  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309032223342D          

 34 39  0  0  1  0            999 V2000
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  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  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  6  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 14  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  6  0  0  0
  4 31  1  0  0  0  0
  4 32  1  1  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0182789

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@]2(C[C@@H](C)[C@]3(C)CC[C@@]4(C)C5=CC[C@H]6C(C)(C)[C@H](O)CC[C@]6(C)[C@@H]5CC[C@@]34O2)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-18-16-29(33-24(18)32)17-19(2)27(6)14-15-28(7)21-8-9-22-25(3,4)23(31)11-12-26(22,5)20(21)10-13-30(27,28)34-29/h8,18-20,22-23,31H,9-17H2,1-7H3/t18-,19-,20-,22+,23-,26-,27+,28+,29-,30-/m1/s1

> <INCHI_KEY>
NLPGKOUOIOJNMX-AYLXSBHYSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.64788483454298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,2'S,4R,5'S,6'R,10'R,13'S,14'R,17'R,19'R)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0^{2,10}.0^{5,10}.0^{14,19}]henicosan]-1'(21')-en-5-one

> <JCHEM_LOGP>
5.880612135333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.554178983374175

> <JCHEM_PKA_STRONGEST_BASIC>
-0.806689345049345

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
133.38199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2'S,4R,5'S,6'R,10'R,13'S,14'R,17'R,19'R)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0^{2,10}.0^{5,10}.0^{14,19}]henicosan]-1'(21')-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.666  -2.789   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.836  -1.787   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.713  -0.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.135   0.339   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.016   1.398   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.374   2.896   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.255   3.955   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.850   3.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.848   4.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.511   4.726   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.038   4.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.321   3.013   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.589   3.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.635   2.211   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.987   2.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.301   2.144   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.263   0.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.577  -0.198   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.140   1.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.087  -0.503   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.539  -1.738   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.853  -2.541   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.187  -2.474   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.872  -1.671   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.911  -0.132   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.558  -0.869   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.596   0.671   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.244  -0.066   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.275   1.003   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.968   2.277   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.611   0.779   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       7.136  -0.830   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.334  -2.144   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.925  -3.566   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31   32                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   30                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   30                                             
CONECT   13   12                                                            
CONECT   14   12   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   17   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   14   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   12    8   31                                             
CONECT   31   30    4                                                       
CONECT   32    4   33                                                       
CONECT   33   32    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(2R,2'S,4R,5'S,6'R,10'R,13'S,14'R,17'R,19'R)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0^{2,10}.0^{5,10}.0^{14,19}]henicosan]-1'(21')-en-5-one

Traditional Name

(2R,2'S,4R,5'S,6'R,10'R,13'S,14'R,17'R,19'R)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0^{2,10}.0^{5,10}.0^{14,19}]henicosan]-1'(21')-en-5-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@]2(C[C@@H](C)[C@]3(C)CC[C@@]4(C)C5=CC[C@H]6C(C)(C)[C@H](O)CC[C@]6(C)[C@@H]5CC[C@@]34O2)OC1=O

InChI Identifier

InChI=1S/C30H46O4/c1-18-16-29(33-24(18)32)17-19(2)27(6)14-15-28(7)21-8-9-22-25(3,4)23(31)11-12-26(22,5)20(21)10-13-30(27,28)34-29/h8,18-20,22-23,31H,9-17H2,1-7H3/t18-,19-,20-,22+,23-,26-,27+,28+,29-,30-/m1/s1

InChI Key

NLPGKOUOIOJNMX-AYLXSBHYSA-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 withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Ketal
Gamma butyrolactone
Oxane
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Carbonyl group
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	5.88	ChemAxon
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	133.38 m³·mol⁻¹	ChemAxon
Polarizability	54.65 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

24571135

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46243533

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one (NP0182789)

MOL for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

3D MOL for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

3D SDF for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

3D-SDF for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

PDB for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

3D PDB for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

SMILES for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

INCHI for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

Structure for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)

3D Structure for NP0182789 ((2r,2's,4r,5's,6'r,10'r,13's,14'r,17'r,19'r)-17'-hydroxy-2',4,5',6',14',18',18'-heptamethyl-9'-oxaspiro[oxolane-2,8'-pentacyclo[11.8.0.0²,¹⁰.0⁵,¹⁰.0¹⁴,¹⁹]henicosan]-1'(21')-en-5-one)