NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate (NP0324948)

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Record Information

Version

2.0

Created at

2022-09-12 05:20:04 UTC

Updated at

2022-09-12 05:20:04 UTC

NP-MRD ID

NP0324948

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207202D          

 39 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309122207202D          

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 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  6  0  0  0
  9 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
  6 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0324948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O)C=C(O)C=C3[C@](O)(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/C27H24O12/c1-11-7-14-18(16(29)8-11)20(31)19-15(9-13(28)10-17(19)30)27(14,36)39-26-23(34)21(32)22(33)25(38-26)37-24(35)12-5-3-2-4-6-12/h2-10,21-23,25-26,28-30,32-34,36H,1H3/t21-,22+,23+,25+,26-,27+/m0/s1

> <INCHI_KEY>
DEVGXIYJHCQNAZ-KGLQBNQBSA-N

> <FORMULA>
C27H24O12

> <MOLECULAR_WEIGHT>
540.477

> <EXACT_MASS>
540.126776213

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.7212914465842

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
4.179860043333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.567896737352328

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.574994122981067

> <JCHEM_PKA_STRONGEST_BASIC>
-3.712120994695195

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
131.42810000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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       4.991  -1.950   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.011  -1.950   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.538  -3.397   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.548  -4.577   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.075  -6.024   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.085  -7.203   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.568  -6.936   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.041  -5.489   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.422  -8.116   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.105  -9.563   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.885 -10.743   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.402 -10.475   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.928  -9.028   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.938  -7.848   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.591  -6.291   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.118  -7.738   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.581  -5.111   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.098  -5.379   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.054  -3.664   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.044  -2.485   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   39  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   38                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   11   30                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   14   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   12   29                                                  
CONECT   29   28                                                            
CONECT   30    9   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30   38                                                  
CONECT   38   37    6   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₇H₂₄O₁₂

Average Mass

540.4770 Da

Monoisotopic Mass

540.12678 Da

IUPAC Name

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

Traditional Name

(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-{[(9R)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-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@](O)(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/C27H24O12/c1-11-7-14-18(16(29)8-11)20(31)19-15(9-13(28)10-17(19)30)27(14,36)39-26-23(34)21(32)22(33)25(38-26)37-24(35)12-5-3-2-4-6-12/h2-10,21-23,25-26,28-30,32-34,36H,1H3/t21-,22+,23+,25+,26-,27+/m0/s1

InChI Key

DEVGXIYJHCQNAZ-KGLQBNQBSA-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
Monocyclic benzene moiety
Monosaccharide
Oxane
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Ketone
Polyol
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Organic oxide
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	4.18	ChemAxon
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.43 m³·mol⁻¹	ChemAxon
Polarizability	50.72 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

162974126

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,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate (NP0324948)

MOL for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

3D MOL for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

3D SDF for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

3D-SDF for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

PDB for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

3D PDB for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

SMILES for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

INCHI for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

Structure for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)

3D Structure for NP0324948 ((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-{[(9r)-2,4,5,9-tetrahydroxy-7-methyl-10-oxoanthracen-9-yl]oxy}oxan-2-yl benzoate)