NP-MRD: Showing NP-Card for (3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one (NP0251962)

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Record Information

Version

2.0

Created at

2022-09-07 15:19:21 UTC

Updated at

2022-09-07 15:19:22 UTC

NP-MRD ID

NP0251962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one

Description

Beauveriolide I belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Beauveriolide I is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one was first documented in 2002 (PMID: 12617514). Based on a literature review a significant number of articles have been published on beauveriolide I (PMID: 17803269) (PMID: 31926180) (PMID: 23252879) (PMID: 22790951) (PMID: 19396893).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217192D          

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M  END

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M  END


  Mrv1652309072217192D          

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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  4  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  4  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  4  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  7 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC[C@H](C)[C@@H]1CC(O)=N[C@@H](CC2=CC=CC=C2)C(O)=N[C@@H](C)C(O)=N[C@H](CC(C)C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H41N3O5/c1-6-7-11-18(4)23-16-24(31)29-21(15-20-12-9-8-10-13-20)26(33)28-19(5)25(32)30-22(14-17(2)3)27(34)35-23/h8-10,12-13,17-19,21-23H,6-7,11,14-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t18-,19-,21-,22+,23-/m0/s1

> <INCHI_KEY>
ZKSLFHXTWGEITF-JIORRVSTSA-N

> <FORMULA>
C27H41N3O5

> <MOLECULAR_WEIGHT>
487.641

> <EXACT_MASS>
487.304621432

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.54695082606185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,6S,9S,13S)-9-benzyl-13-[(2S)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one

> <JCHEM_LOGP>
3.3324398914414397

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.8534710444921543

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.998281747979476

> <JCHEM_PKA_STRONGEST_BASIC>
4.417361375329832

> <JCHEM_POLAR_SURFACE_AREA>
124.07000000000001

> <JCHEM_REFRACTIVITY>
134.52040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6S,9S,13S)-9-benzyl-13-[(2S)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one

> <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      -4.465  -3.318   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.132  -4.088   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.798  -3.318   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.464  -4.088   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.869  -3.318   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.869  -1.778   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.203  -4.088   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.477  -2.573   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.003  -2.365   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.732  -1.008   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       4.672  -3.752   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.203  -4.457   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.440  -3.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.853  -4.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.090  -3.238   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.503  -3.852   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.677  -5.382   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.440  -6.298   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.027  -5.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.410  -5.983   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.836  -6.566   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       5.193  -6.926   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       5.401  -8.452   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.826  -9.035   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.183  -9.395   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.391 -10.921   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0       2.758  -8.812   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       2.550  -7.286   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.332  -8.229   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.540  -9.755   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.965 -10.338   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.322 -10.698   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.124  -6.703   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.093  -7.646   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.917  -5.177   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   12   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    7                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁N₃O₅

Average Mass

487.6410 Da

Monoisotopic Mass

487.30462 Da

IUPAC Name

(3R,6S,9S,13S)-9-benzyl-13-[(2S)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one

Traditional Name

(3R,6S,9S,13S)-9-benzyl-13-[(2S)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one

CAS Registry Number

Not Available

SMILES

CCCC[C@H](C)[C@@H]1CC(O)=N[C@@H](CC2=CC=CC=C2)C(O)=N[C@@H](C)C(O)=N[C@H](CC(C)C)C(=O)O1

InChI Identifier

InChI=1S/C27H41N3O5/c1-6-7-11-18(4)23-16-24(31)29-21(15-20-12-9-8-10-13-20)26(33)28-19(5)25(32)30-22(14-17(2)3)27(34)35-23/h8-10,12-13,17-19,21-23H,6-7,11,14-16H2,1-5H3,(H,28,33)(H,29,31)(H,30,32)/t18-,19-,21-,22+,23-/m0/s1

InChI Key

ZKSLFHXTWGEITF-JIORRVSTSA-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 cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.33	ChemAxon
pKa (Strongest Acidic)	3	ChemAxon
pKa (Strongest Basic)	4.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	124.07 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.52 m³·mol⁻¹	ChemAxon
Polarizability	54.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00016129

Chemspider ID

8088999

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9913349

PDB ID

Not Available

ChEBI ID

180490

Good Scents ID

Not Available

References

General References

Tomoda H, Doi T: Discovery and combinatorial synthesis of fungal metabolites beauveriolides, novel antiatherosclerotic agents. Acc Chem Res. 2008 Jan;41(1):32-9. doi: 10.1021/ar700117b. Epub 2007 Sep 6. [PubMed:17803269 ]
Wang X, Gao YL, Zhang ML, Zhang HD, Huang JZ, Li L: Genome mining and biosynthesis of the Acyl-CoA:cholesterol acyltransferase inhibitor beauveriolide I and III in Cordyceps militaris. J Biotechnol. 2020 Feb 10;309:85-91. doi: 10.1016/j.jbiotec.2020.01.002. Epub 2020 Jan 8. [PubMed:31926180 ]
Huang HJ, Jian YR, Chen CY: Traditional Chinese medicine application in HIV: an in silico study. J Biomol Struct Dyn. 2014;32(1):1-12. doi: 10.1080/07391102.2012.745168. Epub 2012 Dec 20. [PubMed:23252879 ]
Nakaya S, Mizuno S, Ishigami H, Yamakawa Y, Kawagishi H, Ushimaru T: New rapid screening method for anti-aging compounds using budding yeast and identification of beauveriolide I as a potent active compound. Biosci Biotechnol Biochem. 2012;76(6):1226-8. doi: 10.1271/bbb.110872. Epub 2012 Jun 7. [PubMed:22790951 ]
Witter DP, Chen Y, Rogel JK, Boldt GE, Wentworth P Jr: The natural products beauveriolide I and III: a new class of beta-amyloid-lowering compounds. Chembiochem. 2009 May 25;10(8):1344-7. doi: 10.1002/cbic.200900139. [PubMed:19396893 ]
Namatame I, Matsuda D, Tomoda H, Yamaguchi Y, Masuma R, Kobayashi S, Omura S: Selective production of fungal beauveriolide I or III by fermentation in amino acid-supplemented media. J Antibiot (Tokyo). 2002 Dec;55(12):1048-52. doi: 10.7164/antibiotics.55.1048. [PubMed:12617514 ]
LOTUS database [Link]

Showing NP-Card for (3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one (NP0251962)

MOL for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D MOL for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D SDF for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D-SDF for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

PDB for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D PDB for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

SMILES for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

INCHI for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

Structure for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)

3D Structure for NP0251962 ((3r,6s,9s,13s)-9-benzyl-13-[(2s)-hexan-2-yl]-5,8,11-trihydroxy-6-methyl-3-(2-methylpropyl)-1-oxa-4,7,10-triazacyclotrideca-4,7,10-trien-2-one)