NP-MRD: Showing NP-Card for 7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione (NP0322543)

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Record Information

Version

1.0

Created at

2022-09-12 01:22:17 UTC

Updated at

2022-09-12 01:22:17 UTC

NP-MRD ID

NP0322543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione

Description

7,9,16-Trihydroxy-13,14-dimethoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,8-dione belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione is found in Chrysosporium queenslandicum. It was first documented in 2021 (PMID: 34472195). Based on a literature review a significant number of articles have been published on 7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,8-dione (PMID: 34293549) (PMID: 35284724) (PMID: 34200810) (PMID: 34121546).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122203222D          

 28 29  0  0  0  0            999 V2000
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   -0.7145   -1.2375    0.0000 O   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
   -0.0000   -2.4750    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
    0.7145   -3.7125    0.0000 O   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  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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 27 28  2  0  0  0  0
M  END

     RDKit          3D

 54 55  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309122203222D          

 28 29  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   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
   -0.0000   -2.4750    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
    0.7145   -3.7125    0.0000 O   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  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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 12  8  1  4  0  0  0
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M  END
> <DATABASE_ID>
NP0322543

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(C=CCC(O)C(=O)C(O)CCCC(C)OC2=O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O8/c1-11-6-4-8-13(21)18(24)14(22)9-5-7-12-17(20(25)28-11)15(23)10-16(26-2)19(12)27-3/h5,7,10-11,13-14,21-23H,4,6,8-9H2,1-3H3

> <INCHI_KEY>
PUUOBLVKESWSLM-UHFFFAOYSA-N

> <FORMULA>
C20H26O8

> <MOLECULAR_WEIGHT>
394.42

> <EXACT_MASS>
394.162767797

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.332436250027925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,8-dione

> <JCHEM_LOGP>
2.620256554666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.999568806533489

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.089484473885594

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5288044054200656

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
102.26939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3H-2-benzoxacyclotetradecine-1,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   27                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26    7   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₈

Average Mass

394.4200 Da

Monoisotopic Mass

394.16277 Da

IUPAC Name

7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,8-dione

Traditional Name

7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3H-2-benzoxacyclotetradecine-1,8-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(C=CCC(O)C(=O)C(O)CCCC(C)OC2=O)=C1OC

InChI Identifier

InChI=1S/C20H26O8/c1-11-6-4-8-13(21)18(24)14(22)9-5-7-12-17(20(25)28-11)15(23)10-16(26-2)19(12)27-3/h5,7,10-11,13-14,21-23H,4,6,8-9H2,1-3H3

InChI Key

PUUOBLVKESWSLM-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

Species Name	Source	Reference
Chrysosporium queenslandicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Vinylogous acid
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Polyol
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen 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	2.62	ChemAxon
pKa (Strongest Acidic)	10.09	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.27 m³·mol⁻¹	ChemAxon
Polarizability	39.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162858622

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vera P, Canellas E, Nerin C, Dreolin N, Goshawk J: The migration of NIAS from ethylene-vinyl acetate corks and their identification using gas chromatography mass spectrometry and liquid chromatography ion mobility quadrupole time-of-flight mass spectrometry. Food Chem. 2022 Jan 1;366:130592. doi: 10.1016/j.foodchem.2021.130592. Epub 2021 Jul 14. [PubMed:34293549 ]
Faure MDM, Dindault C, Rice NA, Lessard BH: Layer-by-Layer Organic Photovoltaic Solar Cells Using a Solution-Processed Silicon Phthalocyanine Non-Fullerene Acceptor. ACS Omega. 2022 Feb 22;7(9):7541-7549. doi: 10.1021/acsomega.1c05715. eCollection 2022 Mar 8. [PubMed:35284724 ]
Li Y, Li Q, Wang X, Fu Q, Hu C, Qiu X, Li T, Wang F: Eliminating the Detrimental Effect of Secondary Doping on PEDOT : PSS Hole Transporting Material Performance. ChemSusChem. 2021 Nov 4;14(21):4802-4811. doi: 10.1002/cssc.202101458. Epub 2021 Sep 29. [PubMed:34472195 ]
Liu H, Hussain S, Lee J, Vikraman D, Kang J: Ultrasonically Processed WSe(2) Nanosheets Blended Bulk Heterojunction Active Layer for High-Performance Polymer Solar Cells and X-ray Detectors. Materials (Basel). 2021 Jun 10;14(12):3206. doi: 10.3390/ma14123206. [PubMed:34200810 ]
Silpa KP, Chakraborty K: Cistobislactone, an undescribed variant of 14-membered bislactonic macrodiolide, from old-lady octopus Cistopus indicus (family Octopodidae) attenuates inflammatory lipoxygenase. Nat Prod Res. 2022 Jun;36(12):3002-3012. doi: 10.1080/14786419.2021.1938041. Epub 2021 Jun 14. [PubMed:34121546 ]
LOTUS database [Link]

Showing NP-Card for 7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione (NP0322543)

MOL for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

3D MOL for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

3D SDF for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

3D-SDF for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

PDB for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

3D PDB for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

SMILES for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

INCHI for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

Structure for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)

3D Structure for NP0322543 (7,9,16-trihydroxy-13,14-dimethoxy-3-methyl-4,5,6,7,9,10-hexahydro-3h-2-benzoxacyclotetradecine-1,8-dione)