NP-MRD: Showing NP-Card for Chryso-obtusin glucoside (NP0051597)

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Record Information

Version

2.0

Created at

2022-04-27 22:54:13 UTC

Updated at

2022-04-27 22:54:13 UTC

NP-MRD ID

NP0051597

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chryso-obtusin glucoside

Description

1,2,3,8-Tetramethoxy-6-methyl-7-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Chryso-obtusin glucoside is found in Cassia tora , Cassia obtusifolia and Senna tora. Based on a literature review very few articles have been published on 1,2,3,8-tetramethoxy-6-methyl-7-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200542D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282200542D          

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M  END
> <DATABASE_ID>
NP0051597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]4O)=C3OC)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O12/c1-9-6-10-14(18(29)15-11(16(10)27)7-12(32-2)22(33-3)24(15)35-5)23(34-4)21(9)37-25-20(31)19(30)17(28)13(8-26)36-25/h6-7,13,17,19-20,25-26,28,30-31H,8H2,1-5H3/t13-,17-,19-,20-,25+/m1/s1

> <INCHI_KEY>
QBFJCZWBSLFTEE-ZJRSUVDASA-N

> <FORMULA>
C25H28O12

> <MOLECULAR_WEIGHT>
520.487

> <EXACT_MASS>
520.158076342

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.79577405134222

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,3,8-tetramethoxy-6-methyl-7-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
0.22980898633333324

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19603858833797

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200001229171416

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923560972586

> <JCHEM_POLAR_SURFACE_AREA>
170.44

> <JCHEM_REFRACTIVITY>
126.17029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,3,8-tetramethoxy-6-methyl-7-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.002   1.540   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
CONECT    1    2    6   36                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   32                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25                                                            
CONECT   31   24                                                            
CONECT   32   23                                                            
CONECT   33   16                                                            
CONECT   34    2   35                                                       
CONECT   35   34                                                            
CONECT   36    1   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₁₂

Average Mass

520.4870 Da

Monoisotopic Mass

520.15808 Da

IUPAC Name

1,2,3,8-tetramethoxy-6-methyl-7-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione

Traditional Name

1,2,3,8-tetramethoxy-6-methyl-7-{[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}anthracene-9,10-dione

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(OC)=C2C(=O)C3=C(C=C(C)C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]4O)=C3OC)C(=O)C2=C1

InChI Identifier

InChI=1S/C25H28O12/c1-9-6-10-14(18(29)15-11(16(10)27)7-12(32-2)22(33-3)24(15)35-5)23(34-4)21(9)37-25-20(31)19(30)17(28)13(8-26)36-25/h6-7,13,17,19-20,25-26,28,30-31H,8H2,1-5H3/t13-,17-,19-,20-,25+/m1/s1

InChI Key

QBFJCZWBSLFTEE-ZJRSUVDASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cassia tora	Plant	KNApSAcK
Senna obtusifolia	Plant	KNApSAcK
Senna tora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Anthraquinone
9,10-anthraquinone
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Aryl ketone
Anisole
Alkyl aryl ether
Oxane
Monosaccharide
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
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	0.61	ALOGPS
logP	0.23	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.17 m³·mol⁻¹	ChemAxon
Polarizability	51.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

154496341

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Chryso-obtusin glucoside (NP0051597)

MOL for NP0051597 (Chryso-obtusin glucoside)

3D MOL for NP0051597 (Chryso-obtusin glucoside)

3D SDF for NP0051597 (Chryso-obtusin glucoside)

3D-SDF for NP0051597 (Chryso-obtusin glucoside)

PDB for NP0051597 (Chryso-obtusin glucoside)

3D PDB for NP0051597 (Chryso-obtusin glucoside)

SMILES for NP0051597 (Chryso-obtusin glucoside)

INCHI for NP0051597 (Chryso-obtusin glucoside)

Structure for NP0051597 (Chryso-obtusin glucoside)

3D Structure for NP0051597 (Chryso-obtusin glucoside)