NP-MRD: Showing NP-Card for 15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione (NP0172002)

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Record Information

Version

2.0

Created at

2022-09-03 08:45:33 UTC

Updated at

2022-09-03 08:45:33 UTC

NP-MRD ID

NP0172002

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione

Description

15-Chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]Hexacosa-4,13(23),14,16(22)-tetraene-6,9-dione belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione is found in Salinispora tropica. 15-Chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]Hexacosa-4,13(23),14,16(22)-tetraene-6,9-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181500492D          

 37 43  0  0  0  0            999 V2000
    7.5131    1.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4089    0.5614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8177   -0.1551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5975    0.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395    0.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8752    0.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5601   -0.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748    0.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3967    2.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630    2.4027    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    6.3627    2.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004181500492D          

 37 43  0  0  0  0            999 V2000
    7.5131    1.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8033    0.6999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 36  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  2  0  0  0  0
 10 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(=O)OCC(O)C2=CC(Cl)=C3C(O)C45OC6=C(C)C(=O)C11OC1C6(O)OC4(C(O)CC5O)C3=C2

> <INCHI_IDENTIFIER>
InChI=1S/C24H23ClO12/c1-7-15(29)21-18(33-2)19(31)34-6-11(26)8-3-9-14(10(25)4-8)16(30)23-13(28)5-12(27)22(9,23)37-24(32,17(7)35-23)20(21)36-21/h3-4,11-13,16,18,20,26-28,30,32H,5-6H2,1-2H3

> <INCHI_KEY>
CYXHIOKLZVVCBQ-UHFFFAOYSA-N

> <FORMULA>
C24H23ClO12

> <MOLECULAR_WEIGHT>
538.89

> <EXACT_MASS>
538.0878039

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.64786252030292

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione

> <ALOGPS_LOGP>
-0.04

> <JCHEM_LOGP>
-1.0678407833333337

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.64807938631493

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.740952307139317

> <JCHEM_PKA_STRONGEST_BASIC>
-3.372675625497556

> <JCHEM_POLAR_SURFACE_AREA>
184.73999999999998

> <JCHEM_REFRACTIVITY>
119.1417

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      14.024   2.091   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.699   1.306   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.791   2.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.097   1.048   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.860  -0.290   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.582   0.478   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.980   0.213   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.367   0.433   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.779  -0.990   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.060   1.423   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   2.208   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.607   3.781   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       1.238   4.485   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       3.916   4.643   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.409   6.144   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.491   7.380   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.994   6.183   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.499   6.549   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.125   5.795   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.687   6.261   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.017   7.765   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.877   5.216   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.335   5.710   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.569   3.667   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.193   2.173   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.088   3.246   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.919   4.234   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.355   4.789   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.517   3.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.433   4.773   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.931   5.384   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.361   4.814   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.281   7.072   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.753   7.579   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.187   9.011   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.228   3.821   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.321   2.294   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   37                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   36                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   30   34                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    3   25   26                                             
CONECT   25   24   26                                                       
CONECT   26   25   24   27                                                  
CONECT   27   26   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   17   31   36                                             
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   17   35                                                  
CONECT   35   34                                                            
CONECT   36   30   14   37                                                  
CONECT   37   36   10                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₃ClO₁₂

Average Mass

538.8900 Da

Monoisotopic Mass

538.08780 Da

IUPAC Name

15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione

Traditional Name

15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione

CAS Registry Number

Not Available

SMILES

COC1C(=O)OCC(O)C2=CC(Cl)=C3C(O)C45OC6=C(C)C(=O)C11OC1C6(O)OC4(C(O)CC5O)C3=C2

InChI Identifier

InChI=1S/C24H23ClO12/c1-7-15(29)21-18(33-2)19(31)34-6-11(26)8-3-9-14(10(25)4-8)16(30)23-13(28)5-12(27)22(9,23)37-24(32,17(7)35-23)20(21)36-21/h3-4,11-13,16,18,20,26-28,30,32H,5-6H2,1-2H3

InChI Key

CYXHIOKLZVVCBQ-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
Salinispora tropica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Indane
Cyclohexenone
Para-dioxane
Aryl chloride
Aryl halide
Benzenoid
Cyclic alcohol
Vinylogous ester
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Organohalogen compound
Organooxygen compound
Carbonyl group
Organochloride
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-0.04	ALOGPS
logP	-1.1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	184.74 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	119.14 m³·mol⁻¹	ChemAxon
Polarizability	48.65 Å³	ChemAxon
Number of Rings	7	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

72818039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione (NP0172002)

MOL for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

3D MOL for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

3D SDF for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

3D-SDF for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

PDB for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

3D PDB for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

SMILES for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

INCHI for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

Structure for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)

3D Structure for NP0172002 (15-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,25-tetraoxaheptacyclo[11.8.2.2³,⁷.1⁴,¹⁸.0¹,¹⁸.0¹⁶,²².0⁷,²⁶]hexacosa-4,13,15,22-tetraene-6,9-dione)