NP-MRD: Showing NP-Card for 5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one (NP0160654)

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Record Information

Version

1.0

Created at

2022-09-02 18:39:19 UTC

Updated at

2022-09-02 18:39:19 UTC

NP-MRD ID

NP0160654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one

Description

Mosinone A belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Mosinone A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Mosinone A has been detected, but not quantified in, fruits. 5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one is found in Annona squamosa. It was first documented in 2000 (PMID: 11413487). This could make mosinone a a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305492D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061305492D          

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   -1.3819    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2751   -0.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3587    2.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    2.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9356   -1.5157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4773    2.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6107   -0.8483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4681    0.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2780    0.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
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 19 18  1  0  0  0  0
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 23 16  1  0  0  0  0
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 26 25  1  0  0  0  0
 29  2  1  0  0  0  0
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 38 29  2  0  0  0  0
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 44 35  1  0  0  0  0
 44 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC\C=C/CCC(O)C1CCC(O1)C(O)CCCCCC(=O)CCCCC1CC(CC(C)=O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C37H64O7/c1-3-4-5-6-7-8-9-10-11-12-13-16-23-33(40)35-25-26-36(44-35)34(41)24-17-14-15-20-31(39)21-18-19-22-32-28-30(27-29(2)38)37(42)43-32/h12-13,30,32-36,40-41H,3-11,14-28H2,1-2H3/b13-12-

> <INCHI_KEY>
MEZMFFSHBLPWKU-SEYXRHQNSA-N

> <FORMULA>
C37H64O7

> <MOLECULAR_WEIGHT>
620.8999

> <EXACT_MASS>
620.465204402

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
75.96429191981812

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(11-hydroxy-11-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one

> <ALOGPS_LOGP>
7.15

> <JCHEM_LOGP>
8.230829968666667

> <ALOGPS_LOGS>
-6.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.495907503468363

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.893757939987257

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148665083868692

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
176.7808

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.22e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(11-hydroxy-11-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      18.640 -17.983   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.706   2.886   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.014 -16.576   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.919 -15.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.293 -13.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.198 -12.677   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.571 -11.270   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.477 -10.025   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.850  -8.618   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.755  -7.372   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.129  -5.965   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.034  -4.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.408  -3.312   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.090   1.675   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.756   2.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.876  -3.151   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.423   2.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.421   2.445   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.088   1.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.422   1.675   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.755   1.675   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.250  -1.744   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.757   1.675   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.862   1.157   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.831   2.302   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.548   1.318   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.986   2.302   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.175   2.725   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.017   1.157   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.089   2.445   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.580   1.675   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.718  -1.583   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.091   2.445   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.092  -0.177   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.425   1.675   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.247  -0.177   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.270   3.971   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       4.089   3.985   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      14.813  -2.829   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      12.091   3.985   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -4.873  -1.583   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.740   0.144   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      13.586   0.144   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   29                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   16                                                       
CONECT   14   15   17                                                       
CONECT   15   14   20                                                       
CONECT   16   13   23                                                       
CONECT   17   14   24                                                       
CONECT   18   19   21                                                       
CONECT   19   18   22                                                       
CONECT   20   15   31                                                       
CONECT   21   18   31                                                       
CONECT   22   19   32                                                       
CONECT   23   16   33                                                       
CONECT   24   17   34                                                       
CONECT   25   26   35                                                       
CONECT   26   25   36                                                       
CONECT   27   29   30                                                       
CONECT   28   30   32                                                       
CONECT   29    2   27   38                                                  
CONECT   30   27   28   37                                                  
CONECT   31   20   21   39                                                  
CONECT   32   22   28   43                                                  
CONECT   33   23   35   40                                                  
CONECT   34   24   36   41                                                  
CONECT   35   25   33   44                                                  
CONECT   36   26   34   44                                                  
CONECT   37   30   42   43                                                  
CONECT   38   29                                                            
CONECT   39   31                                                            
CONECT   40   33                                                            
CONECT   41   34                                                            
CONECT   42   37                                                            
CONECT   43   32   37                                                       
CONECT   44   35   36                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

View in JSmol

Synonyms

Value	Source
Mosinone a	MeSH

Chemical Formula

C₃₇H₆₄O₇

Average Mass

620.8999 Da

Monoisotopic Mass

620.46520 Da

IUPAC Name

5-(11-hydroxy-11-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one

Traditional Name

5-(11-hydroxy-11-{5-[(4Z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC\C=C/CCC(O)C1CCC(O1)C(O)CCCCCC(=O)CCCCC1CC(CC(C)=O)C(=O)O1

InChI Identifier

InChI=1S/C37H64O7/c1-3-4-5-6-7-8-9-10-11-12-13-16-23-33(40)35-25-26-36(44-35)34(41)24-17-14-15-20-31(39)21-18-19-22-32-28-30(27-29(2)38)37(42)43-32/h12-13,30,32-36,40-41H,3-11,14-28H2,1-2H3/b13-12-

InChI Key

MEZMFFSHBLPWKU-SEYXRHQNSA-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
Annona squamosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	7.15	ALOGPS
logP	8.23	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	176.78 m³·mol⁻¹	ChemAxon
Polarizability	75.96 Å³	ChemAxon
Number of Rings	2	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

HMDB0031228

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003252

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

131751150

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
LOTUS database [Link]

Showing NP-Card for 5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one (NP0160654)

MOL for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

3D MOL for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

3D SDF for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

3D-SDF for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

PDB for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

3D PDB for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

SMILES for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

INCHI for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

Structure for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)

3D Structure for NP0160654 (5-(11-hydroxy-11-{5-[(4z)-1-hydroxypentadec-4-en-1-yl]oxolan-2-yl}-5-oxoundecyl)-3-(2-oxopropyl)oxolan-2-one)