NP-MRD: Showing NP-Card for methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate (NP0276211)

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Record Information

Version

2.0

Created at

2022-09-09 00:12:54 UTC

Updated at

2022-09-09 00:12:54 UTC

NP-MRD ID

NP0276211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate

Description

Colletotrichin belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate is found in Colletotrichum nicotianae. Based on a literature review very few articles have been published on Colletotrichin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092202122D          

 35 37  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0915   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3631   -3.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -4.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8199   -4.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  1  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
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  9 10  1  0  0  0  0
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  5 12  1  0  0  0  0
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 16 17  1  0  0  0  0
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 16 19  1  0  0  0  0
  6 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  6  0  0  0
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 32 33  1  0  0  0  0
 29 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END

     RDKit          3D

 77 79  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309092202122D          

 35 37  0  0  1  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
  6 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0276211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(C)OC(OC)=C(C[C@H]2C(=C)CC[C@@H]3[C@@](C)(CCC(C)(C)O)[C@@H](O)CC[C@@]23C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O7/c1-16-9-10-20-27(5,12-11-21(29)28(20,6)14-13-26(3,4)32)19(16)15-18-23(30)22(24(31)33-7)17(2)35-25(18)34-8/h19-21,29,32H,1,9-15H2,2-8H3/t19-,20-,21-,27-,28+/m0/s1

> <INCHI_KEY>
IUNGBSYMDFEAMS-KPRONASWSA-N

> <FORMULA>
C28H42O7

> <MOLECULAR_WEIGHT>
490.637

> <EXACT_MASS>
490.293053692

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.71597076810856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 5-{[(1S,4aS,5R,6S,8aS)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxo-4H-pyran-3-carboxylate

> <JCHEM_LOGP>
4.194954290666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.834809111522805

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.390464973623278

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5929030900381164

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
144.76130000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 5-{[(1S,4aS,5R,6S,8aS)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.678  -6.382   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.314  -8.465   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.397  -7.828   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.573   0.294   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8   20                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20    6    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   29   22   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₇

Average Mass

490.6370 Da

Monoisotopic Mass

490.29305 Da

IUPAC Name

methyl 5-{[(1S,4aS,5R,6S,8aS)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxo-4H-pyran-3-carboxylate

Traditional Name

methyl 5-{[(1S,4aS,5R,6S,8aS)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(C)OC(OC)=C(C[C@H]2C(=C)CC[C@@H]3[C@@](C)(CCC(C)(C)O)[C@@H](O)CC[C@@]23C)C1=O

InChI Identifier

InChI=1S/C28H42O7/c1-16-9-10-20-27(5,12-11-21(29)28(20,6)14-13-26(3,4)32)19(16)15-18-23(30)22(24(31)33-7)17(2)35-25(18)34-8/h19-21,29,32H,1,9-15H2,2-8H3/t19-,20-,21-,27-,28+/m0/s1

InChI Key

IUNGBSYMDFEAMS-KPRONASWSA-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
Colletotrichum nicotianae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Alkyl aryl ether
Pyranone
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Vinylogous ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.19	ChemAxon
pKa (Strongest Acidic)	18.39	ChemAxon
pKa (Strongest Basic)	-0.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	144.76 m³·mol⁻¹	ChemAxon
Polarizability	54.72 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

84259

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

93332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate (NP0276211)

MOL for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

3D MOL for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

3D SDF for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

3D-SDF for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

PDB for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

3D PDB for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

SMILES for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

INCHI for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

Structure for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)

3D Structure for NP0276211 (methyl 5-{[(1s,4as,5r,6s,8as)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-6-methoxy-2-methyl-4-oxopyran-3-carboxylate)