NP-MRD: Showing NP-Card for n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid (NP0226749)

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Record Information

Version

2.0

Created at

2022-09-06 05:53:12 UTC

Updated at

2022-09-06 05:53:13 UTC

NP-MRD ID

NP0226749

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid

Description

N-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Based on a literature review very few articles have been published on N-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062207532D          

 37 40  0  0  0  0            999 V2000
    5.4217    0.1644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309062207532D          

 37 40  0  0  0  0            999 V2000
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   -2.6693    4.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5416    4.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704    5.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1868    4.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8864    4.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2156    3.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    3.2131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437    3.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3721    3.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6149    4.4748    0.0000 O   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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 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
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 34 33  1  4  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226749

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NC1C(O)C(O)C(CO)OC1OCC1(C)C(O)CCC2(C)C1CC(=O)C1=C2CCC(C)(C1)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H43NO8/c1-6-26(3)9-7-17-16(12-26)18(32)11-20-27(17,4)10-8-21(33)28(20,5)14-36-25-22(29-15(2)31)24(35)23(34)19(13-30)37-25/h6,19-25,30,33-35H,1,7-14H2,2-5H3,(H,29,31)

> <INCHI_KEY>
RLULVWNWQFIJAC-UHFFFAOYSA-N

> <FORMULA>
C28H43NO8

> <MOLECULAR_WEIGHT>
521.651

> <EXACT_MASS>
521.298867349

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.61021910102816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid

> <JCHEM_LOGP>
1.4137018579999991

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.894283195094708

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.80120226434664

> <JCHEM_PKA_STRONGEST_BASIC>
1.6325100240332786

> <JCHEM_POLAR_SURFACE_AREA>
149.04

> <JCHEM_REFRACTIVITY>
136.3707

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.121   0.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.850   4.366   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.904   5.905   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.263   6.628   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.317   8.167   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.677   8.890   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.983   8.074   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.011   8.983   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.065  10.522   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.349   8.260   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.655   9.076   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.402   6.721   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       1.762   5.998   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       3.068   6.814   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.428   6.091   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.014   8.353   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    9                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13    7   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
N-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidate	Generator

Chemical Formula

C₂₈H₄₃NO₈

Average Mass

521.6510 Da

Monoisotopic Mass

521.29887 Da

IUPAC Name

N-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid

Traditional Name

N-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NC1C(O)C(O)C(CO)OC1OCC1(C)C(O)CCC2(C)C1CC(=O)C1=C2CCC(C)(C1)C=C

InChI Identifier

InChI=1S/C28H43NO8/c1-6-26(3)9-7-17-16(12-26)18(32)11-20-27(17,4)10-8-21(33)28(20,5)14-36-25-22(29-15(2)31)24(35)23(34)19(13-30)37-25/h6,19-25,30,33-35H,1,7-14H2,2-5H3,(H,29,31)

InChI Key

RLULVWNWQFIJAC-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Pimarane diterpenoid
Diterpenoid
Steroid
N-acyl-alpha-hexosamine
Hydrophenanthrene
Phenanthrene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Oxane
Monosaccharide
Acetamide
Cyclic alcohol
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Ketone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Primary alcohol
Organooxygen compound
Organonitrogen compound
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	1.41	ChemAxon
pKa (Strongest Acidic)	5.8	ChemAxon
pKa (Strongest Basic)	1.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.04 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.37 m³·mol⁻¹	ChemAxon
Polarizability	56.61 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	Yes	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

76032337

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid (NP0226749)

MOL for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

3D MOL for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

3D SDF for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

3D-SDF for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

PDB for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

3D PDB for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

SMILES for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

INCHI for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

Structure for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)

3D Structure for NP0226749 (n-{2-[(7-ethenyl-2-hydroxy-1,4a,7-trimethyl-9-oxo-2,3,4,5,6,8,10,10a-octahydrophenanthren-1-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}ethanimidic acid)