NP-MRD: Showing NP-Card for 4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one (NP0168271)

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Record Information

Version

2.0

Created at

2022-09-03 04:02:22 UTC

Updated at

2022-09-03 04:02:22 UTC

NP-MRD ID

NP0168271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one

Description

4-{10,11-Dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]Octacosa-8,15-dien-8-yl}-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as 14-hydroxysteroids. These are steroids carrying a hydroxyl group at the 14-position of the steroid backbone. 4-{10,11-Dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]Octacosa-8,15-dien-8-yl}-2,5-dihydrofuran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231515292D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004231515292D          

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    6.4819    0.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4080    1.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8622   -0.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6813   -1.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8407   -1.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5893   -2.1758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1201   -2.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5154   -1.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 21 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C(CCC4=CC5OC6OCCC7OCOC67OC5CC34C)C1(O)C(O)C=C2C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O9/c1-26-12-21-20(37-25-29(38-21)23(6-8-33-25)35-14-36-29)10-16(26)3-4-18-17(26)5-7-27(2)19(11-22(30)28(18,27)32)15-9-24(31)34-13-15/h9-11,17-18,20-23,25,30,32H,3-8,12-14H2,1-2H3

> <INCHI_KEY>
JSDHSHRUWUICQY-UHFFFAOYSA-N

> <FORMULA>
C29H36O9

> <MOLECULAR_WEIGHT>
528.598

> <EXACT_MASS>
528.235932739

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.748564207485586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.1648458446666665

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.022541434668664

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.217842480074588

> <JCHEM_PKA_STRONGEST_BASIC>
-3.429704083389603

> <JCHEM_POLAR_SURFACE_AREA>
112.91000000000001

> <JCHEM_REFRACTIVITY>
133.40939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       8.323  -0.208   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.025   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.865   0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.408   0.788   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.639  -0.034   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.791   0.272   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.113  -0.518   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.770  -2.019   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.236  -2.157   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.631  -0.741   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.174  -0.243   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.124   1.268   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.036   2.281   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.493   1.783   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.653   2.796   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.111   2.299   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.270   3.312   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.728   2.814   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.887   3.827   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.345   3.329   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.642   1.818   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.483   0.805   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.780  -0.706   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.237  -1.203   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.397  -0.190   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.851  -1.662   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.926  -0.374   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.574   1.023   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.445   2.071   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.629   3.600   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.100   1.321   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.962   2.855   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.676  -1.719   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.205  -1.903   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.503  -3.414   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      17.900  -4.062   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      15.158  -4.164   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.029  -3.117   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10   14                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    4   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    2   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   31                                                  
CONECT   22   21    2   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   21   25   32                                             
CONECT   32   31                                                            
CONECT   33   27   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   33                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₉

Average Mass

528.5980 Da

Monoisotopic Mass

528.23593 Da

IUPAC Name

4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-2,5-dihydrofuran-2-one

Traditional Name

4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4=CC5OC6OCCC7OCOC67OC5CC34C)C1(O)C(O)C=C2C1=CC(=O)OC1

InChI Identifier

InChI=1S/C29H36O9/c1-26-12-21-20(37-25-29(38-21)23(6-8-33-25)35-14-36-29)10-16(26)3-4-18-17(26)5-7-27(2)19(11-22(30)28(18,27)32)15-9-24(31)34-13-15/h9-11,17-18,20-23,25,30,32H,3-8,12-14H2,1-2H3

InChI Key

JSDHSHRUWUICQY-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 14-hydroxysteroids. These are steroids carrying a hydroxyl group at the 14-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

14-hydroxysteroids

Alternative Parents

Substituents

14-hydroxysteroid
Dioxolopyran
Ketal
Para-dioxane
2-furanone
Oxane
Meta-dioxolane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
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	2.22	ALOGPS
logP	2.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.22	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	112.91 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.41 m³·mol⁻¹	ChemAxon
Polarizability	55.75 Å³	ChemAxon
Number of Rings	8	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

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

14586313

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one (NP0168271)

MOL for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

3D MOL for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

3D SDF for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

3D-SDF for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

PDB for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

3D PDB for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

SMILES for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

INCHI for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

Structure for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)

3D Structure for NP0168271 (4-{10,11-dihydroxy-3,7-dimethyl-18,20,24,26,28-pentaoxaheptacyclo[15.11.0.0³,¹⁵.0⁴,¹².0⁷,¹¹.0¹⁹,²⁷.0²³,²⁷]octacosa-8,15-dien-8-yl}-5h-furan-2-one)