NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate (NP0243664)

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Record Information

Version

2.0

Created at

2022-09-07 04:15:54 UTC

Updated at

2022-09-07 04:15:54 UTC

NP-MRD ID

NP0243664

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate

Description

(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-{[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9,10-dihydroanthracen-9-yl]oxy}oxan-2-yl benzoate belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. (2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate is found in Picramnia teapensis. Based on a literature review very few articles have been published on (2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-{[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9,10-dihydroanthracen-9-yl]oxy}oxan-2-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206152D          

 38 42  0  0  1  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072206152D          

 38 42  0  0  1  0            999 V2000
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 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0243664

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3[C@H](O[C@@H]3O[C@@H](OC(=O)C4=CC=CC=C4)[C@H](O)[C@H](O)[C@H]3O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O11/c1-11-7-14-18(16(29)8-11)20(31)19-15(9-13(28)10-17(19)30)24(14)36-26-22(33)21(32)23(34)27(38-26)37-25(35)12-5-3-2-4-6-12/h2-10,21-24,26-30,32-34H,1H3/t21-,22-,23-,24-,26-,27-/m1/s1

> <INCHI_KEY>
WVWKIPOZHVGDJJ-XXCXBFEJSA-N

> <FORMULA>
C27H24O11

> <MOLECULAR_WEIGHT>
524.478

> <EXACT_MASS>
524.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
50.2255383497556

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-{[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9,10-dihydroanthracen-9-yl]oxy}oxan-2-yl benzoate

> <JCHEM_LOGP>
4.369544085

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.666221914867258

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.665793856226547

> <JCHEM_PKA_STRONGEST_BASIC>
-3.712050957545139

> <JCHEM_POLAR_SURFACE_AREA>
183.21

> <JCHEM_REFRACTIVITY>
129.96080000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-{[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]oxy}oxan-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.001   3.850   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   37                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   13   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   11   28                                                  
CONECT   28   27                                                            
CONECT   29    9   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29   37                                                  
CONECT   37   36    6   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R,5R,6R)-3,4,5-Trihydroxy-6-{[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9,10-dihydroanthracen-9-yl]oxy}oxan-2-yl benzoic acid	Generator

Chemical Formula

C₂₇H₂₄O₁₁

Average Mass

524.4780 Da

Monoisotopic Mass

524.13186 Da

IUPAC Name

(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-{[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9,10-dihydroanthracen-9-yl]oxy}oxan-2-yl benzoate

Traditional Name

(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-{[(9R)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]oxy}oxan-2-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3[C@H](O[C@@H]3O[C@@H](OC(=O)C4=CC=CC=C4)[C@H](O)[C@H](O)[C@H]3O)C2=C1

InChI Identifier

InChI=1S/C27H24O11/c1-11-7-14-18(16(29)8-11)20(31)19-15(9-13(28)10-17(19)30)24(14)36-26-22(33)21(32)23(34)27(38-26)37-25(35)12-5-3-2-4-6-12/h2-10,21-24,26-30,32-34H,1H3/t21-,22-,23-,24-,26-,27-/m1/s1

InChI Key

WVWKIPOZHVGDJJ-XXCXBFEJSA-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
Picramnia teapensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Glycosyl compound
O-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.37	ChemAxon
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.96 m³·mol⁻¹	ChemAxon
Polarizability	50.23 Å³	ChemAxon
Number of Rings	5	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

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

162962455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate (NP0243664)

MOL for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

3D MOL for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

3D SDF for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

3D-SDF for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

PDB for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

3D PDB for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

SMILES for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

INCHI for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

Structure for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)

3D Structure for NP0243664 ((2s,3r,4r,5r,6r)-3,4,5-trihydroxy-6-{[(9r)-2,4,5-trihydroxy-7-methyl-10-oxo-9h-anthracen-9-yl]oxy}oxan-2-yl benzoate)