NP-MRD: Showing NP-Card for 3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol (NP0187645)

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Record Information

Version

2.0

Created at

2022-09-04 03:50:52 UTC

Updated at

2022-09-04 03:50:52 UTC

NP-MRD ID

NP0187645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

Description

Ilicicolin H belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond. 3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol is found in Calonectria pyrochroa. 3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol was first documented in 2019 (PMID: 31216742). Based on a literature review a small amount of articles have been published on ilicicolin H (PMID: 33573152) (PMID: 35355395) (PMID: 34947016) (PMID: 30905148).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205502D          

 32 35  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434    1.2375    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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    3.0613   -0.1370   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042205502D          

 32 35  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0187645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\[C@@H]1[C@H]2C[C@@H](C)CC[C@@H]2C(C)=C[C@H]1C(=O)C1=C(O)N=CC(C2=CC=C(O)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO4/c1-4-5-20-21-12-15(2)6-11-19(21)16(3)13-22(20)25(30)24-26(31)23(14-28-27(24)32)17-7-9-18(29)10-8-17/h4-5,7-10,13-15,19-22,29H,6,11-12H2,1-3H3,(H2,28,31,32)/b5-4+/t15-,19+,20+,21-,22+/m0/s1

> <INCHI_KEY>
BYVVOONSAAQMKI-RFKCMYLBSA-N

> <FORMULA>
C27H31NO4

> <MOLECULAR_WEIGHT>
433.548

> <EXACT_MASS>
433.225308482

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
49.21132183514183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

> <JCHEM_LOGP>
7.039853153333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.179999269947873

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.387160863765958

> <JCHEM_PKA_STRONGEST_BASIC>
0.4118825444046187

> <JCHEM_POLAR_SURFACE_AREA>
90.65

> <JCHEM_REFRACTIVITY>
128.20989999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   21                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
CONECT   21   13    8   22                                                  
CONECT   22   21                                                            
CONECT   23    5   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26    4                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₁NO₄

Average Mass

433.5480 Da

Monoisotopic Mass

433.22531 Da

IUPAC Name

3-[(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

Traditional Name

3-[(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

CAS Registry Number

Not Available

SMILES

C\C=C\[C@@H]1[C@H]2C[C@@H](C)CC[C@@H]2C(C)=C[C@H]1C(=O)C1=C(O)N=CC(C2=CC=C(O)C=C2)=C1O

InChI Identifier

InChI=1S/C27H31NO4/c1-4-5-20-21-12-15(2)6-11-19(21)16(3)13-22(20)25(30)24-26(31)23(14-28-27(24)32)17-7-9-18(29)10-8-17/h4-5,7-10,13-15,19-22,29H,6,11-12H2,1-3H3,(H2,28,31,32)/b5-4+/t15-,19+,20+,21-,22+/m0/s1

InChI Key

BYVVOONSAAQMKI-RFKCMYLBSA-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
Calonectria pyrochroa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

Alternative Parents

Substituents

3-phenylpyridine
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Dihydropyridine
Phenol
Hydroxypyridine
Pyridinone
Monocyclic benzene moiety
Hydropyridine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Ketone
Lactam
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:77772 )
monohydroxypyridine (CHEBI:77772 )
pyridone (CHEBI:77772 )
aromatic ketone (CHEBI:77772 )
carbobicyclic compound (CHEBI:77772 )

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	7.04	ChemAxon
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	0.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.21 m³·mol⁻¹	ChemAxon
Polarizability	49.21 Å³	ChemAxon
Number of Rings	4	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

C00028381

Chemspider ID

8518297

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10342838

PDB ID

Not Available

ChEBI ID

77772

Good Scents ID

Not Available

References

General References

Lin X, Yuan S, Chen S, Chen B, Xu H, Liu L, Li H, Gao Z: Heterologous Expression of Ilicicolin H Biosynthetic Gene Cluster and Production of a New Potent Antifungal Reagent, Ilicicolin J. Molecules. 2019 Jun 18;24(12). pii: molecules24122267. doi: 10.3390/molecules24122267. [PubMed:31216742 ]
Guzman EA, Pitts TP, Tandberg KR, Winder PL, Wright AE: Discovery of Survivin Inhibitors Part 1: Screening the Harbor Branch Pure Compound Library. Mar Drugs. 2021 Jan 30;19(2). pii: md19020073. doi: 10.3390/md19020073. [PubMed:33573152 ]
Young DH, Meunier B, Wang NX: Interaction of picolinamide fungicide primary metabolites UK-2A and CAS-649 with the cytochrome bc(1) complex Qi site: mutation effects and modelling in Saccharomyces cerevisiae. Pest Manag Sci. 2022 Jun;78(6):2657-2666. doi: 10.1002/ps.6893. Epub 2022 Apr 29. [PubMed:35355395 ]
Shenouda ML, Ambilika M, Cox RJ: Trichoderma reesei Contains a Biosynthetic Gene Cluster That Encodes the Antifungal Agent Ilicicolin H. J Fungi (Basel). 2021 Dec 1;7(12):1034. doi: 10.3390/jof7121034. [PubMed:34947016 ]
Zhang Z, Jamieson CS, Zhao YL, Li D, Ohashi M, Houk KN, Tang Y: Enzyme-Catalyzed Inverse-Electron Demand Diels-Alder Reaction in the Biosynthesis of Antifungal Ilicicolin H. J Am Chem Soc. 2019 Apr 10;141(14):5659-5663. doi: 10.1021/jacs.9b02204. Epub 2019 Mar 26. [PubMed:30905148 ]
LOTUS database [Link]

Showing NP-Card for 3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol (NP0187645)

MOL for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D MOL for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D SDF for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D-SDF for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

PDB for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D PDB for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

SMILES for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

INCHI for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

Structure for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)

3D Structure for NP0187645 (3-[(1r,2s,4as,7s,8ar)-4,7-dimethyl-1-[(1e)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonyl]-5-(4-hydroxyphenyl)pyridine-2,4-diol)