NP-MRD: Showing NP-Card for 16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one (NP0207554)

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Record Information

Version

2.0

Created at

2022-09-05 04:12:29 UTC

Updated at

2022-09-05 04:12:29 UTC

NP-MRD ID

NP0207554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one

Description

16-(2-Hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]Tricosa-1(14),3(12),4(9),5,10,18(23),19,21-octaen-13-one belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. 16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one is found in Morus alba. 16-(2-Hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]Tricosa-1(14),3(12),4(9),5,10,18(23),19,21-octaen-13-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241510442D          

 33 37  0  0  0  0            999 V2000
    1.0468    3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7272    4.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077    4.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608    4.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4382    4.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937    3.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0092    3.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6154    2.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5558    2.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386    1.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9810    2.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6639    1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6043    0.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2871    0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0295    0.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2550   -0.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8502    0.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0891    1.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4062    1.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4658    2.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7830    3.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8425    4.0257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    2.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3578    3.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4173    4.1288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    1.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7830    2.6652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  6 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241510442D          

 33 37  0  0  0  0            999 V2000
    1.0468    3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0092    3.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5558    2.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2386    1.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0207554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(OO)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=CC=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O8/c1-24(2)8-7-14-18(32-24)11-16(27)20-21(28)15-10-19(25(3,4)33-29)30-17-9-12(26)5-6-13(17)22(15)31-23(14)20/h5-9,11,19,26-27,29H,10H2,1-4H3

> <INCHI_KEY>
FTIZDJNLUATQGK-UHFFFAOYSA-N

> <FORMULA>
C25H24O8

> <MOLECULAR_WEIGHT>
452.459

> <EXACT_MASS>
452.147117733

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
47.3953867419059

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
4.191376326333333

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.780987144667582

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.539070587780467

> <JCHEM_PKA_STRONGEST_BASIC>
-4.23904657664118

> <JCHEM_POLAR_SURFACE_AREA>
114.68

> <JCHEM_REFRACTIVITY>
120.78479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.954   6.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.224   7.581   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.494   8.452   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.353   8.851   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.818   8.732   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.095   6.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.617   6.544   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.749   5.499   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.638   3.963   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.912   3.099   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.298   3.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.573   2.907   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.461   1.371   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.736   0.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.122   1.178   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.543  -0.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.654   1.335   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.233   2.714   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.958   3.578   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.069   5.114   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.795   5.979   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.906   7.515   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.409   5.307   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.134   6.171   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.246   7.707   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.367   3.093   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.714   1.592   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.588   0.542   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.115   0.992   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.989  -0.058   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.768   2.493   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.895   3.543   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.328   4.975   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   11   24                                                  
CONECT   24   23    8   25                                                  
CONECT   25   24                                                            
CONECT   26    9   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26   33                                                  
CONECT   33   32    6                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₈

Average Mass

452.4590 Da

Monoisotopic Mass

452.14712 Da

IUPAC Name

16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one

Traditional Name

16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one

CAS Registry Number

Not Available

SMILES

CC(C)(OO)C1CC2=C(OC3=C4C=CC(C)(C)OC4=CC(O)=C3C2=O)C2=CC=C(O)C=C2O1

InChI Identifier

InChI=1S/C25H24O8/c1-24(2)8-7-14-18(32-24)11-16(27)20-21(28)15-10-19(25(3,4)33-29)30-17-9-12(26)5-6-13(17)22(15)31-23(14)20/h5-9,11,19,26-27,29H,10H2,1-4H3

InChI Key

FTIZDJNLUATQGK-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
Morus alba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
2,2-dimethyl-1-benzopyran
Benzoxepine
Chromone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Hydroperoxide
Peroxol
Ether
Alkyl hydroperoxide
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	3.89	ALOGPS
logP	4.19	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.54	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	120.78 m³·mol⁻¹	ChemAxon
Polarizability	47.4 Å³	ChemAxon
Number of Rings	5	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

5481972

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one (NP0207554)

MOL for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

3D MOL for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

3D SDF for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

3D-SDF for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

PDB for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

3D PDB for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

SMILES for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

INCHI for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

Structure for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)

3D Structure for NP0207554 (16-(2-hydroperoxypropan-2-yl)-11,20-dihydroxy-7,7-dimethyl-2,8,17-trioxapentacyclo[12.9.0.0³,¹².0⁴,⁹.0¹⁸,²³]tricosa-1(14),3,5,9,11,18,20,22-octaen-13-one)