NP-MRD: Showing NP-Card for (4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione (NP0211988)

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Record Information

Version

2.0

Created at

2022-09-05 10:30:16 UTC

Updated at

2022-09-05 10:30:16 UTC

NP-MRD ID

NP0211988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione

Description

Phlogacanathoside B belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione is found in Phlogacanthus curviflorus. Based on a literature review very few articles have been published on Phlogacanathoside B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052212302D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052212302D          

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 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
 18 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
  6 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2[C@@H](CC3=C(CC[C@@H]4[C@](C)(CO[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)CCC[C@@]34C)C2=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O9/c1-12-18-15(34-23(12)32)9-14-13(19(18)28)5-6-17-25(2,7-4-8-26(14,17)3)11-33-24-22(31)21(30)20(29)16(10-27)35-24/h15-17,20-22,24,27,29-31H,4-11H2,1-3H3/t15-,16-,17-,20-,21+,22-,24-,25+,26+/m1/s1

> <INCHI_KEY>
GVSBVIDYKKDTET-DUYHXFDGSA-N

> <FORMULA>
C26H36O9

> <MOLECULAR_WEIGHT>
492.565

> <EXACT_MASS>
492.235932739

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.270741731187066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,6R,7S,16R)-2,6,13-trimethyl-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-1(10),12-diene-11,14-dione

> <JCHEM_LOGP>
1.3252870023333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.215172983058633

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.242624497228604

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083413061718

> <JCHEM_POLAR_SURFACE_AREA>
142.75000000000003

> <JCHEM_REFRACTIVITY>
123.63730000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6R,7S,16R)-2,6,13-trimethyl-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-1(10),12-diene-11,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.928   4.480   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.090  -0.539   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.813  -0.198   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.842  -0.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.176   2.211   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.337   3.487   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.998   4.254   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.002   5.794   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.338   6.561   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.341   8.101   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.677   8.868   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.009   8.094   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.009   8.874   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.013  10.414   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.326   8.107   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.658   8.881   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.330   6.567   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.665   5.801   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.380   3.667   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.896   3.938   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   35                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
CONECT   13    7   14   15   33                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   33                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   18   13   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34    6                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₉

Average Mass

492.5650 Da

Monoisotopic Mass

492.23593 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=C2[C@@H](CC3=C(CC[C@@H]4[C@](C)(CO[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)CCC[C@@]34C)C2=O)OC1=O

InChI Identifier

InChI=1S/C26H36O9/c1-12-18-15(34-23(12)32)9-14-13(19(18)28)5-6-17-25(2,7-4-8-26(14,17)3)11-33-24-22(31)21(30)20(29)16(10-27)35-24/h15-17,20-22,24,27,29-31H,4-11H2,1-3H3/t15-,16-,17-,20-,21+,22-,24-,25+,26+/m1/s1

InChI Key

GVSBVIDYKKDTET-DUYHXFDGSA-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
Phlogacanthus curviflorus	LOTUS Database	35616633

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
Diterpene lactone
Abietane diterpenoid
Diterpenoid
Naphthofuran
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexenone
2-furanone
Oxane
Monosaccharide
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Organooxygen 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

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

9342884

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11167789

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione (NP0211988)

MOL for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

3D MOL for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

3D SDF for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

3D-SDF for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

PDB for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

3D PDB for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

SMILES for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

INCHI for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

Structure for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)

3D Structure for NP0211988 ((4r,4as,10ar,11br)-4,8,11b-trimethyl-4-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1h,2h,3h,4ah,5h,6h,10ah,11h-phenanthro[3,2-b]furan-7,9-dione)