NP-MRD: Showing NP-Card for (1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione (NP0282409)

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Record Information

Version

2.0

Created at

2022-09-09 09:13:37 UTC

Updated at

2022-09-09 09:13:38 UTC

NP-MRD ID

NP0282409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione

Description

Uredinorubellin I belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. (1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione is found in Ramularia uredinicola. Based on a literature review very few articles have been published on uredinorubellin I.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092211132D          

 40 46  0  0  1  0            999 V2000
    1.4610   -0.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -1.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1836   -3.4046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4846   -2.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -2.1426    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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 38 39  1  0  0  0  0
 17 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092211132D          

 40 46  0  0  1  0            999 V2000
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  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 20 19  1  1  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  2  0  0  0  0
 18 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 31 38  1  0  0  0  0
 38 39  1  0  0  0  0
 17 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0282409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=C1)[C@H](O)[C@]13CC4=CC(O)=C5C(=O)C6=C(O)C=CC(O)=C6C(=O)C5=C4[C@H]1C=C[C@@H](O)[C@@]3(O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O10/c1-10-6-12-20(16(33)7-10)28(39)30(40)18(35)5-2-13-19-11(9-29(13,30)27(12)38)8-17(34)23-24(19)26(37)22-15(32)4-3-14(31)21(22)25(23)36/h2-8,13,18,27,31-35,38,40H,9H2,1H3/t13-,18-,27+,29+,30-/m1/s1

> <INCHI_KEY>
GFXZZUIOUAYGTP-GVQITLLHSA-N

> <FORMULA>
C30H22O10

> <MOLECULAR_WEIGHT>
542.496

> <EXACT_MASS>
542.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
54.11046300812343

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,17R,20R,21R,29S)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0^{1,21}.0^{3,16}.0^{6,15}.0^{8,13}.0^{23,28}]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione

> <JCHEM_LOGP>
4.603912308666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.378714578248728

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.828462236980105

> <JCHEM_PKA_STRONGEST_BASIC>
-3.390933828991961

> <JCHEM_POLAR_SURFACE_AREA>
192.81999999999996

> <JCHEM_REFRACTIVITY>
141.74969999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,17R,20R,21R,29S)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0^{1,21}.0^{3,16}.0^{6,15}.0^{8,13}.0^{23,28}]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       2.727  -1.046   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.364  -2.448   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.468  -3.701   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.105  -5.103   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.209  -6.355   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.638  -5.252   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.534  -3.999   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.897  -2.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.659  -3.996   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.962  -2.896   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.703  -5.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.372  -4.047   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.700  -3.267   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.009  -1.758   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.470  -1.271   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.778   0.237   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.622  -2.293   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.313  -3.802   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.852  -4.289   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.236  -5.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.873  -7.103   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.977  -8.355   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.445  -8.206   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.549  -9.458   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.808  -6.804   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.912  -8.056   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.275  -6.654   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.379  -7.907   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.465  -4.824   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.156  -6.333   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.926  -4.337   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.078  -5.359   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.769  -6.867   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      16.539  -4.872   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.848  -3.363   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.696  -2.341   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      16.005  -0.833   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.235  -2.828   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.083  -1.806   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.392  -0.298   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   27                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   20   25                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   39                                                  
CONECT   18   17   19   29                                                  
CONECT   19   18   13   20                                                  
CONECT   20   19   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   11   26   27                                             
CONECT   26   25                                                            
CONECT   27   25    6   28                                                  
CONECT   28   27                                                            
CONECT   29   18   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   38                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   31   39                                                  
CONECT   39   38   17   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₀

Average Mass

542.4960 Da

Monoisotopic Mass

542.12130 Da

IUPAC Name

(1S,17R,20R,21R,29S)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0^{1,21}.0^{3,16}.0^{6,15}.0^{8,13}.0^{23,28}]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione

Traditional Name

(1S,17R,20R,21R,29S)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0^{1,21}.0^{3,16}.0^{6,15}.0^{8,13}.0^{23,28}]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=C1)[C@H](O)[C@]13CC4=CC(O)=C5C(=O)C6=C(O)C=CC(O)=C6C(=O)C5=C4[C@H]1C=C[C@@H](O)[C@@]3(O)C2=O

InChI Identifier

InChI=1S/C30H22O10/c1-10-6-12-20(16(33)7-10)28(39)30(40)18(35)5-2-13-19-11(9-29(13,30)27(12)38)8-17(34)23-24(19)26(37)22-15(32)4-3-14(31)21(22)25(23)36/h2-8,13,18,27,31-35,38,40H,9H2,1H3/t13-,18-,27+,29+,30-/m1/s1

InChI Key

GFXZZUIOUAYGTP-GVQITLLHSA-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
Ramularia uredinicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Fluorene
Tetralin
Indane
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Tertiary alcohol
Ketone
1,2-diol
Secondary alcohol
Polyol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	ChemAxon
pKa (Strongest Acidic)	7.83	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	192.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	141.75 m³·mol⁻¹	ChemAxon
Polarizability	54.11 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040602

Chemspider ID

24709393

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44578392

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione (NP0282409)

MOL for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

3D MOL for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

3D SDF for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

3D-SDF for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

PDB for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

3D PDB for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

SMILES for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

INCHI for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

Structure for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)

3D Structure for NP0282409 ((1s,17r,20r,21r,29s)-5,9,12,20,21,24,29-heptahydroxy-26-methylheptacyclo[15.12.0.0¹,²¹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²³,²⁸]nonacosa-3,5,8,10,12,15,18,23,25,27-decaene-7,14,22-trione)