NP-MRD: Showing NP-Card for 11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one (NP0328354)

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Record Information

Version

1.0

Created at

2022-09-12 11:45:14 UTC

Updated at

2022-09-12 11:45:15 UTC

NP-MRD ID

NP0328354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one

Description

Neoacrimarine H belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Neoacrimarine H is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Neoacrimarine H has been detected, but not quantified in, citrus. 11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one is found in Citrus aurantium. This could make neoacrimarine H a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061306522D          

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M  END

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  Mrv0541 05061306522D          

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    6.8724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -4.9204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -7.7783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7474   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349   -7.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8724   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9224   -6.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4599   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 14 13  2  0  0  0  0
 16  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18  7  1  0  0  0  0
 19 15  2  0  0  0  0
 20 11  1  0  0  0  0
 21  8  2  0  0  0  0
 22 15  1  0  0  0  0
 22 17  2  0  0  0  0
 23 12  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  2  0  0  0  0
 26 18  2  0  0  0  0
 26 21  1  0  0  0  0
 27 17  1  0  0  0  0
 27 24  2  0  0  0  0
 28 18  1  0  0  0  0
 28 24  1  0  0  0  0
 29 16  2  0  0  0  0
 29 25  1  0  0  0  0
 30 25  1  0  0  0  0
 31 30  1  0  0  0  0
 32  1  1  0  0  0  0
 32  2  1  0  0  0  0
 32 14  1  0  0  0  0
 33  3  1  0  0  0  0
 33  4  1  0  0  0  0
 33 31  1  0  0  0  0
 34  5  1  0  0  0  0
 34 26  1  0  0  0  0
 34 27  1  0  0  0  0
 35 19  1  0  0  0  0
 36 23  2  0  0  0  0
 37 28  2  0  0  0  0
 38 31  1  0  0  0  0
 39 21  1  0  0  0  0
 39 30  1  0  0  0  0
 40 23  1  0  0  0  0
 40 29  1  0  0  0  0
 41 22  1  0  0  0  0
 41 32  1  0  0  0  0
 42 20  1  0  0  0  0
 42 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(C=CC=C2OC2C(O)C(C)(C)OC3=C2C2=C(C=CC(=O)O2)C=C3)C(=O)C2=C1C1=C(OC(C)(C)C=C1)C=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C33H29NO8/c1-32(2)14-13-17-22(41-32)15-19(35)24-27(17)34(5)26-18(28(24)37)7-6-8-21(26)39-30-25-20(42-33(3,4)31(30)38)11-9-16-10-12-23(36)40-29(16)25/h6-15,30-31,35,38H,1-5H3

> <INCHI_KEY>
KYDGDSAPWLVOME-UHFFFAOYSA-N

> <FORMULA>
C33H29NO8

> <MOLECULAR_WEIGHT>
567.5853

> <EXACT_MASS>
567.189316909

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
58.287187298626776

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
11-hydroxy-6-({13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-14-yl}oxy)-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
5.544316221666666

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.829101221606528

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.141133247051693

> <JCHEM_PKA_STRONGEST_BASIC>
-3.748741998497093

> <JCHEM_POLAR_SURFACE_AREA>
114.76000000000002

> <JCHEM_REFRACTIVITY>
156.083

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-6-({13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-14-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.639  -9.529   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.639 -11.508   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.008  -4.840   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.008  -2.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.438  -7.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.828  -9.185   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.058 -10.518   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.058  -7.851   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.208  -1.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.898  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748  -1.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.128  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.128  -9.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.588  -9.185   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.898 -13.186   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.438  -2.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.898 -10.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.518 -10.518   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.438 -13.186   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.518  -2.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.518  -7.851   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.128 -11.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.898  -5.184   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.208 -11.852   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.748  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.748  -9.185   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.438 -10.518   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.748 -11.852   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.208  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.518  -5.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.058  -5.184   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.818 -10.518   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.828  -3.850   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       8.208  -9.185   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0       8.208 -14.519   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.128  -6.517   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      10.518 -13.186   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      12.828  -6.517   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       9.748  -6.517   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       7.438  -5.184   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       3.588 -11.852   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      12.058  -2.516   0.000  0.00  0.00           O+0
CONECT    1   32                                                            
CONECT    2   32                                                            
CONECT    3   33                                                            
CONECT    4   33                                                            
CONECT    5   34                                                            
CONECT    6    7    8                                                       
CONECT    7    6   18                                                       
CONECT    8    6   21                                                       
CONECT    9   11   16                                                       
CONECT   10   12   16                                                       
CONECT   11    9   20                                                       
CONECT   12   10   23                                                       
CONECT   13   14   17                                                       
CONECT   14   13   32                                                       
CONECT   15   19   22                                                       
CONECT   16    9   10   29                                                  
CONECT   17   13   22   27                                                  
CONECT   18    7   26   28                                                  
CONECT   19   15   24   35                                                  
CONECT   20   11   25   42                                                  
CONECT   21    8   26   39                                                  
CONECT   22   15   17   41                                                  
CONECT   23   12   36   40                                                  
CONECT   24   19   27   28                                                  
CONECT   25   20   29   30                                                  
CONECT   26   18   21   34                                                  
CONECT   27   17   24   34                                                  
CONECT   28   18   24   37                                                  
CONECT   29   16   25   40                                                  
CONECT   30   25   31   39                                                  
CONECT   31   30   33   38                                                  
CONECT   32    1    2   14   41                                             
CONECT   33    3    4   31   42                                             
CONECT   34    5   26   27                                                  
CONECT   35   19                                                            
CONECT   36   23                                                            
CONECT   37   28                                                            
CONECT   38   31                                                            
CONECT   39   21   30                                                       
CONECT   40   23   29                                                       
CONECT   41   22   32                                                       
CONECT   42   20   33                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Value	Source
(+)-Neoacrimarine-H	HMDB

Chemical Formula

C₃₃H₂₉NO₈

Average Mass

567.5853 Da

Monoisotopic Mass

567.18932 Da

IUPAC Name

11-hydroxy-6-({13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-14-yl}oxy)-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

Traditional Name

11-hydroxy-6-({13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-14-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one

CAS Registry Number

Not Available

SMILES

CN1C2=C(C=CC=C2OC2C(O)C(C)(C)OC3=C2C2=C(C=CC(=O)O2)C=C3)C(=O)C2=C1C1=C(OC(C)(C)C=C1)C=C2O

InChI Identifier

InChI=1S/C33H29NO8/c1-32(2)14-13-17-22(41-32)15-19(35)24-27(17)34(5)26-18(28(24)37)7-6-8-21(26)39-30-25-20(42-33(3,4)31(30)38)11-9-16-10-12-23(36)40-29(16)25/h6-15,30-31,35,38H,1-5H3

InChI Key

KYDGDSAPWLVOME-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
Citrus aurantium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Pyranocoumarin
Angular pyranocoumarin
Pyranochromene
Chromenopyridine
2,2-dimethyl-1-benzopyran
Coumarin
Dihydroquinolone
Dihydroquinoline
1-benzopyran
Benzopyran
Chromane
Pyranone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyran
Benzenoid
Pyridine
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Secondary alcohol
Lactone
Azacycle
Ether
Oxacycle
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
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	4.6	ALOGPS
logP	5.54	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	10.14	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	156.08 m³·mol⁻¹	ChemAxon
Polarizability	58.29 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033031

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011023

KNApSAcK ID

C00024226

Chemspider ID

8682617

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10507216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one (NP0328354)

MOL for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

3D MOL for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

3D SDF for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

3D-SDF for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

PDB for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

3D PDB for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

SMILES for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

INCHI for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

Structure for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)

3D Structure for NP0328354 (11-hydroxy-6-({9-hydroxy-8,8-dimethyl-2-oxo-9h,10h-pyrano[2,3-h]chromen-10-yl}oxy)-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one)