NP-MRD: Showing NP-Card for 5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione (NP0194079)

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Record Information

Version

2.0

Created at

2022-09-04 11:40:16 UTC

Updated at

2022-09-04 11:40:16 UTC

NP-MRD ID

NP0194079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione

Description

Lactoquinomycin B belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. 5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione is found in Streptomyces tanashiensis. Lactoquinomycin B is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231514152D          

 34 39  0  0  0  0            999 V2000
   -2.1008   -0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5446   -0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -0.5698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826   -1.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322   -1.9655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2379   -2.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5999   -1.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875   -2.9289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2933   -3.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9313   -3.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6232   -1.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2347   -0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0405   -0.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901    0.3155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967   -1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529   -1.6895    0.0000 O   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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M  END

     RDKit          3D

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    5.5929   -0.7789   -0.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.5730    0.2164   -0.0423 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0005    1.3792    0.4728 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2221    2.9160    0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9502    0.2088   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
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 11 42  1  0
M  END


  Mrv1533004231514152D          

 34 39  0  0  0  0            999 V2000
   -2.1008   -0.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5446   -0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388   -0.5698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0194079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC(C1O)N(C)C)C1=CC=C2C(=O)C34OC3(C(C)OC3CC(=O)OC43)C(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO9/c1-9-18(27)13(25(3)4)7-14(31-9)11-5-6-12-17(19(11)28)21(30)23-10(2)32-15-8-16(26)33-22(15)24(23,34-23)20(12)29/h5-6,9-10,13-15,18,22,27-28H,7-8H2,1-4H3

> <INCHI_KEY>
UKGUMAYTBDAONQ-UHFFFAOYSA-N

> <FORMULA>
C24H27NO9

> <MOLECULAR_WEIGHT>
473.478

> <EXACT_MASS>
473.168581453

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.56421292495666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
0.3811407602299059

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.608587815532683

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2667758540044884

> <JCHEM_PKA_STRONGEST_BASIC>
7.97486906625424

> <JCHEM_POLAR_SURFACE_AREA>
135.13

> <JCHEM_REFRACTIVITY>
114.81189999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione

> <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      -3.922  -0.257   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.883  -1.394   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.379  -1.064   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.341  -2.201   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.807  -3.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.311  -3.999   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.349  -2.862   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.853  -3.192   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -2.777  -5.467   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -4.281  -5.798   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.738  -6.605   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.163  -1.870   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.629  -0.403   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.133  -0.072   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.171  -1.210   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.676  -0.879   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.141   0.589   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.714  -2.016   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.752  -3.154   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.248  -3.484   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.286  -4.622   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.820  -6.089   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.790  -4.291   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.256  -2.823   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.659  -2.187   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.487  -0.657   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.625   0.381   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       8.979  -0.347   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.218  -1.686   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.744  -3.815   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.278  -5.283   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.706  -2.677   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.202  -3.008   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.736  -4.476   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   29                                             
CONECT   19   18   20                                                       
CONECT   20   19   18   21   30                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   18   24                                                  
CONECT   30   20   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   15   33                                                  
CONECT   33   32   12   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₇NO₉

Average Mass

473.4780 Da

Monoisotopic Mass

473.16858 Da

IUPAC Name

5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione

Traditional Name

5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione

CAS Registry Number

Not Available

SMILES

CC1OC(CC(C1O)N(C)C)C1=CC=C2C(=O)C34OC3(C(C)OC3CC(=O)OC43)C(=O)C2=C1O

InChI Identifier

InChI=1S/C24H27NO9/c1-9-18(27)13(25(3)4)7-14(31-9)11-5-6-12-17(19(11)28)21(30)23-10(2)32-15-8-16(26)33-22(15)24(23,34-23)20(12)29/h5-6,9-10,13-15,18,22,27-28H,7-8H2,1-4H3

InChI Key

UKGUMAYTBDAONQ-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
Streptomyces tanashiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Naphthalene
Tetralin
Furopyran
Quinone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1,4-dioxepane
Pyranone
Dioxepane
Aralkylamine
Pyran
Monosaccharide
Oxane
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Furan
Vinylogous acid
1,2-aminoalcohol
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Ketone
Tertiary aliphatic amine
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Alcohol
Amine
Organopnictogen compound
Organooxygen compound
Organonitrogen 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	1.48	ALOGPS
logP	0.38	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.81 m³·mol⁻¹	ChemAxon
Polarizability	48.56 Å³	ChemAxon
Number of Rings	6	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

130509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione (NP0194079)

MOL for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

3D MOL for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

3D SDF for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

3D-SDF for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

PDB for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

3D PDB for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

SMILES for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

INCHI for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

Structure for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)

3D Structure for NP0194079 (5-[4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16,18-trioxapentacyclo[8.7.1.0¹,¹⁰.0³,⁸.0¹¹,¹⁵]octadeca-3,5,7-triene-2,9,13-trione)