NP-MRD: Showing NP-Card for 5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one (NP0280254)

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Record Information

Version

2.0

Created at

2022-09-09 05:56:19 UTC

Updated at

2022-09-09 05:56:19 UTC

NP-MRD ID

NP0280254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one

Description

Muricadienin 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. Muricadienin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Muricadienin has been detected, but not quantified in, fruits. 5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one is found in Annona muricata. This could make muricadienin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061306452D          

 37 37  0  0  0  0            999 V2000
  -10.0037    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4119    8.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5748    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8603    2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8603    2.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1458    3.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4313    4.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
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 19 18  2  0  0  0  0
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 21 20  1  0  0  0  0
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 27 26  1  0  0  0  0
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 35 34  1  0  0  0  0
 36 35  2  0  0  0  0
 37 33  1  0  0  0  0
 37 35  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 05061306452D          

 37 37  0  0  0  0            999 V2000
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   -7.1458    3.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1458    4.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4313    4.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4313    5.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7169    5.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0024    5.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0024    4.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2879    4.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5735    4.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5735    5.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8590    5.7744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8590    6.5994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5735    7.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5735    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8590    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4300    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7134    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713    7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394    7.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914    8.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2857    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3720    9.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7589    9.6220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1789    9.2414    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  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 33  2  1  0  0  0  0
 33 32  1  0  0  0  0
 34 31  1  0  0  0  0
 34 32  2  0  0  0  0
 35 34  1  0  0  0  0
 36 35  2  0  0  0  0
 37 33  1  0  0  0  0
 37 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC\C=C/CC\C=C/CCCCCCCCCCCCC1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H62O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-34-32-33(2)37-35(34)36/h14-15,18-19,32-33H,3-13,16-17,20-31H2,1-2H3/b15-14-,19-18-

> <INCHI_KEY>
ZZXWNKPYSIVFNM-XUWLZAGCSA-N

> <FORMULA>
C35H62O2

> <MOLECULAR_WEIGHT>
514.8656

> <EXACT_MASS>
514.474981228

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
69.49864774439746

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
10.82

> <JCHEM_LOGP>
13.51738907433333

> <ALOGPS_LOGS>
-7.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.115322232239539

> <JCHEM_PKA_STRONGEST_BASIC>
-6.879887748924184

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
165.68550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.65e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]-5H-furan-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     -18.674   1.539   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.969  15.756   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.340   0.769   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.006   1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -16.006   3.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -14.673   3.849   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -14.673   5.389   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.339   6.159   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -13.339   7.699   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.005   8.469   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.005  10.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.672  10.779   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.338  10.009   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.338   8.469   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.004   7.699   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.671   8.469   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.671  10.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.337  10.779   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.337  12.319   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.671  13.089   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.671  14.629   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.337  15.399   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.003  14.629   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.669  15.399   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.336  14.629   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.002  15.399   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.332  14.629   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.665  15.399   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.999  14.629   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.333  15.399   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.666  14.629   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.407  14.773   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.437  15.917   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.000  15.399   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.161  16.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.017  17.961   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       9.667  17.251   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   33                                                            
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   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   34                                                       
CONECT   32   33   34                                                       
CONECT   33    2   32   37                                                  
CONECT   34   31   32   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   33   35                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   74    0
END

View in JSmol

Synonyms

Value	Source
5-Methyl-3-(13,17-triacontadienyl)-2(5H)-furanone	HMDB
Muricadienin	MeSH

Chemical Formula

C₃₅H₆₂O₂

Average Mass

514.8656 Da

Monoisotopic Mass

514.47498 Da

IUPAC Name

5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]-2,5-dihydrofuran-2-one

Traditional Name

5-methyl-3-[(13Z,17Z)-triaconta-13,17-dien-1-yl]-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC\C=C/CC\C=C/CCCCCCCCCCCCC1=CC(C)OC1=O

InChI Identifier

InChI=1S/C35H62O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-34-32-33(2)37-35(34)36/h14-15,18-19,32-33H,3-13,16-17,20-31H2,1-2H3/b15-14-,19-18-

InChI Key

ZZXWNKPYSIVFNM-XUWLZAGCSA-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 muricata	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
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
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	10.82	ALOGPS
logP	13.52	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	15.12	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	165.69 m³·mol⁻¹	ChemAxon
Polarizability	69.5 Å³	ChemAxon
Number of Rings	1	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

HMDB0032850

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010827

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

131751334

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one (NP0280254)

MOL for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

3D MOL for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

3D SDF for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

3D-SDF for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

PDB for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

3D PDB for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

SMILES for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

INCHI for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

Structure for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)

3D Structure for NP0280254 (5-methyl-3-[(13z,17z)-triaconta-13,17-dien-1-yl]-5h-furan-2-one)