NP-MRD: Showing NP-Card for methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate (NP0292326)

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Record Information

Version

2.0

Created at

2022-09-09 23:48:04 UTC

Updated at

2022-09-09 23:48:05 UTC

NP-MRD ID

NP0292326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate

Description

Methyl 1,6-dihydroxy-8,12-dimethyl-11-{[3-(1-methyl-1H-imidazol-4-yl)prop-2-enoyl]oxy}-5-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]Pentadeca-2,7,13-triene-2-carboxylate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Methyl 1,6-dihydroxy-8,12-dimethyl-11-{[3-(1-methyl-1H-imidazol-4-yl)prop-2-enoyl]oxy}-5-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]Pentadeca-2,7,13-triene-2-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161507052D          

 37 40  0  0  0  0            999 V2000
    2.6229   -2.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6930    0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780    0.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780    1.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9084    2.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 33 34  1  0  0  0  0
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 29 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004161507052D          

 37 40  0  0  0  0            999 V2000
    2.6229   -2.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 12  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  5 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
 22 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  7 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 29 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC2C(CC(OC(=O)C=CC3=CN(C)C=N3)C3(C)OC1(O)C=C3)C(C)=CC(O)C2C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H36N2O7/c1-16(2)25-20-12-21(26(33)35-6)28(34)10-9-27(4,37-28)23(13-19(20)17(3)11-22(25)31)36-24(32)8-7-18-14-30(5)15-29-18/h7-12,14-16,19-20,22-23,25,31,34H,13H2,1-6H3

> <INCHI_KEY>
VNBNQVPWVAJOJL-UHFFFAOYSA-N

> <FORMULA>
C28H36N2O7

> <MOLECULAR_WEIGHT>
512.603

> <EXACT_MASS>
512.252251507

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
55.34853255789186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 1,6-dihydroxy-8,12-dimethyl-11-{[3-(1-methyl-1H-imidazol-4-yl)prop-2-enoyl]oxy}-5-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
3.527499139

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.153679245244028

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.797633043137036

> <JCHEM_PKA_STRONGEST_BASIC>
5.946662438912431

> <JCHEM_POLAR_SURFACE_AREA>
120.11000000000001

> <JCHEM_REFRACTIVITY>
139.84980000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       4.896  -3.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.896  -2.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.562  -1.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.229  -2.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.562  -0.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.027   0.396   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.932   1.641   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.932   3.181   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.027   4.427   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.562   4.903   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.562   6.443   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.229   7.213   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.895   6.443   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.229   8.753   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.895   9.523   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.895  11.063   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.351  11.968   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.125  13.433   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -0.780  14.679   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.665  13.433   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.141  11.968   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.098   4.427   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.193   5.673   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.602   2.411   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.098   0.396   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.193  -0.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.193   1.641   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.193   3.181   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.266   3.951   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.600   3.181   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.600   1.641   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.933   0.871   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.266   0.871   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.266  -0.669   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.932  -1.439   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.600  -1.439   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.266   5.491   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   16                                                       
CONECT   22   10   23   24   28                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    5   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29    8   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    7   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   29                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl 1,6-dihydroxy-8,12-dimethyl-11-{[3-(1-methyl-1H-imidazol-4-yl)prop-2-enoyl]oxy}-5-(propan-2-yl)-15-oxatricyclo[10.2.1.0,]pentadeca-2,7,13-triene-2-carboxylic acid	Generator
Methyl 1,6-dihydroxy-8,12-dimethyl-11-{[3-(1-methyl-1H-imidazol-4-yl)prop-2-enoyl]oxy}-5-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylic acid	Generator

Chemical Formula

C₂₈H₃₆N₂O₇

Average Mass

512.6030 Da

Monoisotopic Mass

512.25225 Da

IUPAC Name

methyl 1,6-dihydroxy-8,12-dimethyl-11-{[3-(1-methyl-1H-imidazol-4-yl)prop-2-enoyl]oxy}-5-(propan-2-yl)-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate

Traditional Name

methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2C(CC(OC(=O)C=CC3=CN(C)C=N3)C3(C)OC1(O)C=C3)C(C)=CC(O)C2C(C)C

InChI Identifier

InChI=1S/C28H36N2O7/c1-16(2)25-20-12-21(26(33)35-6)28(34)10-9-27(4,37-28)23(13-19(20)17(3)11-22(25)31)36-24(32)8-7-18-14-30(5)15-29-18/h7-12,14-16,19-20,22-23,25,31,34H,13H2,1-6H3

InChI Key

VNBNQVPWVAJOJL-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
N-substituted imidazole
Fatty acyl
Azole
Dihydrofuran
Imidazole
Heteroaromatic compound
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic nitrogen 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	2.51	ALOGPS
logP	3.53	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.8	ChemAxon
pKa (Strongest Basic)	5.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	120.11 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.85 m³·mol⁻¹	ChemAxon
Polarizability	55.35 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	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

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

73999967

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate (NP0292326)

MOL for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D MOL for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D SDF for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D-SDF for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

PDB for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D PDB for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

SMILES for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

INCHI for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

Structure for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)

3D Structure for NP0292326 (methyl 1,6-dihydroxy-5-isopropyl-8,12-dimethyl-11-{[3-(1-methylimidazol-4-yl)prop-2-enoyl]oxy}-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-2,7,13-triene-2-carboxylate)