NP-MRD: Showing NP-Card for (1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol (NP0154668)

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Record Information

Version

2.0

Created at

2022-09-02 11:36:57 UTC

Updated at

2022-09-02 11:36:57 UTC

NP-MRD ID

NP0154668

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol

Description

Cyathinin D belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol is found in Cyathus subglobisporus. Based on a literature review very few articles have been published on Cyathinin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022213362D          

 34 39  0  0  1  0            999 V2000
    3.5282   -3.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050   -2.7973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1347   -1.9753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3636   -1.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7258   -2.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9316   -2.0489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7276   -1.2495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0624   -1.7376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901   -0.7309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1776   -1.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8567    0.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539    0.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2845    0.1512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0582    0.4376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697   -0.2097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1121   -0.8962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3178   -0.6732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5512   -0.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -0.1394    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8705    0.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3126    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8211    0.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8448   -1.5553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5312   -2.0128    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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  9 10  1  6  0  0  0
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 16  4  1  1  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 15 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
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 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

 72 77  0  0  0  0  0  0  0  0999 V2000
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  3 33  1  0
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M  END


  Mrv1652309022213362D          

 34 39  0  0  1  0            999 V2000
    3.5282   -3.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 15 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  2  0  0  0  0
 23 31  1  0  0  0  0
 32 31  1  1  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0154668

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H](O)[C@@H]2C3=C(CC[C@]3(C)CC[C@@]2(C)[C@H]2O[C@@H]3OC[C@@H](O)[C@]4(O)OC=C1[C@H]2[C@]34O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O8/c1-12(2)13-6-7-23(3)8-9-24(4)18(16(13)23)19(28)20(31-5)14-10-33-26(30)15(27)11-32-22-25(26,29)17(14)21(24)34-22/h10,12,15,17-22,27-30H,6-9,11H2,1-5H3/t15-,17-,18+,19-,20+,21+,22+,23-,24-,25+,26+/m1/s1

> <INCHI_KEY>
AJLJAVRFWUUVNX-SDJLEFBYSA-N

> <FORMULA>
C26H38O8

> <MOLECULAR_WEIGHT>
478.582

> <EXACT_MASS>
478.256668184

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.515489382498096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,10R,11R,12S,16S,17R,20S,21S,22R)-12-methoxy-2,5-dimethyl-8-(propan-2-yl)-15,19,23-trioxahexacyclo[18.2.1.0^{2,10}.0^{5,9}.0^{13,22}.0^{16,21}]tricosa-8,13-diene-11,16,17,21-tetrol

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
1.0827067603333311

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.70827047475321

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.77642204299324

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3280206398650787

> <JCHEM_POLAR_SURFACE_AREA>
117.84000000000002

> <JCHEM_REFRACTIVITY>
121.5401

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,10R,11R,12S,16S,17R,20S,21S,22R)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0^{2,10}.0^{5,9}.0^{13,22}.0^{16,21}]tricosa-8,13-diene-11,16,17,21-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.586  -6.102   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.849  -5.222   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.718  -3.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.279  -3.140   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.088  -4.241   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.606  -3.825   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.225  -2.332   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.983  -3.244   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.661  -1.364   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.331  -2.141   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.599   0.174   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.901   0.998   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.264   0.282   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.709   0.817   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.663  -0.391   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.809  -1.673   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.327  -1.257   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.896  -0.688   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.198  -0.260   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.225   0.934   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.636   1.216   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.134   1.574   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.193   0.457   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.784   1.879   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.733   0.496   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.246  -0.956   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.023  -1.893   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.063  -3.432   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.415  -4.168   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.749  -4.236   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.755  -1.020   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.257  -1.378   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.044  -2.903   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.325  -3.757   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15    4   17                                                  
CONECT   17   16   13    7   18                                             
CONECT   18   17                                                            
CONECT   19   15   20   21   32                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   23   32                                                  
CONECT   32   31   19   33                                                  
CONECT   33   32    3   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

C₂₆H₃₈O₈

Average Mass

478.5820 Da

Monoisotopic Mass

478.25667 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H](O)[C@@H]2C3=C(CC[C@]3(C)CC[C@@]2(C)[C@H]2O[C@@H]3OC[C@@H](O)[C@]4(O)OC=C1[C@H]2[C@]34O)C(C)C

InChI Identifier

InChI=1S/C26H38O8/c1-12(2)13-6-7-23(3)8-9-24(4)18(16(13)23)19(28)20(31-5)14-10-33-26(30)15(27)11-32-22-25(26,29)17(14)21(24)34-22/h10,12,15,17-22,27-30H,6-9,11H2,1-5H3/t15-,17-,18+,19-,20+,21+,22+,23-,24-,25+,26+/m1/s1

InChI Key

AJLJAVRFWUUVNX-SDJLEFBYSA-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
Cyathus subglobisporus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Furopyran
Pyran
Oxane
Monosaccharide
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.64	ALOGPS
logS	-2.8	ALOGPS

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

78439209

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol (NP0154668)

MOL for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

3D MOL for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

3D SDF for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

3D-SDF for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

PDB for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

3D PDB for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

SMILES for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

INCHI for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

Structure for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)

3D Structure for NP0154668 ((1s,2r,5r,10r,11r,12s,16s,17r,20s,21s,22r)-8-isopropyl-12-methoxy-2,5-dimethyl-15,19,23-trioxahexacyclo[18.2.1.0²,¹⁰.0⁵,⁹.0¹³,²².0¹⁶,²¹]tricosa-8,13-diene-11,16,17,21-tetrol)