NP-MRD: Showing NP-Card for 4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one (NP0176464)

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Record Information

Version

2.0

Created at

2022-09-03 14:07:52 UTC

Updated at

2022-09-03 14:07:52 UTC

NP-MRD ID

NP0176464

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one

Description

4,6-Dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-2-one belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one is found in Ixeris chinensis. Based on a literature review very few articles have been published on 4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032216072D          

 31 34  0  0  0  0            999 V2000
    5.6412   -1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -2.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -2.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -2.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851   -1.6863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265   -0.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541   -0.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461    0.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0691    1.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    1.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600    2.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7280    2.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3730    2.4665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3150    3.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    4.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5471    2.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    3.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3439    1.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864    0.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6763    1.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
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 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  6 31  1  0  0  0  0
 14 31  1  0  0  0  0
M  END

     RDKit          3D

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    4.3622    0.5456   -1.2113 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8203    1.0211   -1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6060    0.2539   -2.0293 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.9386   -1.0329 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2186   -1.4818   -1.6519 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4622   -1.3401    0.4122 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0840   -2.6726    0.5296 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6758   -0.4171    1.3066 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5268    0.2443    2.2266 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3941    2.5766   -0.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2338   -1.3509   -1.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032216072D          

 31 34  0  0  0  0            999 V2000
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    4.9157    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0176464

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(O)CC(O)C2C(OC(=O)C2=C)C2C1CC(OC1OC(CO)C(O)C(O)C1O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O10/c1-7-11(29-20-17(26)16(25)15(24)12(6-22)30-20)4-9-13(7)18-14(8(2)19(27)31-18)10(23)5-21(9,3)28/h9-18,20,22-26,28H,1-2,4-6H2,3H3

> <INCHI_KEY>
GOBAOFSBAXNPFM-UHFFFAOYSA-N

> <FORMULA>
C21H30O10

> <MOLECULAR_WEIGHT>
442.461

> <EXACT_MASS>
442.183897166

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.55717336788948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-2-one

> <JCHEM_LOGP>
-2.3119087153333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.175098767831177

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207178860637176

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9350027542992034

> <JCHEM_POLAR_SURFACE_AREA>
166.14000000000001

> <JCHEM_REFRACTIVITY>
103.3319

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      10.530  -1.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.245  -1.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.176   0.433   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.380   1.393   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.691   0.843   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.843  -0.442   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.803  -1.646   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461  -3.148   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.665  -4.108   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.073  -3.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.686  -3.148   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.343  -4.649   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.146  -3.148   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.343  -1.646   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.901  -1.105   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970   0.433   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.766   1.393   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.996   2.916   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.429   3.479   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.659   5.002   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.092   5.564   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.296   4.604   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.455   5.962   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.684   7.485   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.021   5.399   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.183   6.359   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.792   3.876   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.642   3.314   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.455   0.843   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.996   2.285   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.303  -0.442   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    6   14                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₁₀

Average Mass

442.4610 Da

Monoisotopic Mass

442.18390 Da

IUPAC Name

4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1(O)CC(O)C2C(OC(=O)C2=C)C2C1CC(OC1OC(CO)C(O)C(O)C1O)C2=C

InChI Identifier

InChI=1S/C21H30O10/c1-7-11(29-20-17(26)16(25)15(24)12(6-22)30-20)4-9-13(7)18-14(8(2)19(27)31-18)10(23)5-21(9,3)28/h9-18,20,22-26,28H,1-2,4-6H2,3H3

InChI Key

GOBAOFSBAXNPFM-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
Ixeris chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Gamma butyrolactone
Monosaccharide
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Primary 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	-2.3	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	166.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	103.33 m³·mol⁻¹	ChemAxon
Polarizability	44.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

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

163049453

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one (NP0176464)

MOL for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D MOL for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D SDF for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D-SDF for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

PDB for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D PDB for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

SMILES for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

INCHI for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

Structure for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)

3D Structure for NP0176464 (4,6-dihydroxy-6-methyl-3,9-dimethylidene-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydroazuleno[4,5-b]furan-2-one)