NP-MRD: Showing NP-Card for cascaroside c (NP0213810)

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Record Information

Version

2.0

Created at

2022-09-05 12:54:35 UTC

Updated at

2022-09-05 12:54:35 UTC

NP-MRD ID

NP0213810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cascaroside c

Description

Cascaroside C belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. cascaroside c is found in Rheum australe. cascaroside c was first documented in 2004 (PMID: 15056949). Based on a literature review very few articles have been published on Cascaroside C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052214542D          

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    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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  6 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052214542D          

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  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  6  0  0  0
  9 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  1  0  0  0
 25 38  2  0  0  0  0
 21 38  1  0  0  0  0
 38 39  1  0  0  0  0
  6 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0213810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)C3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=CC=C3[C@H]([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O13/c1-9-5-11-16(26-24(36)22(34)19(31)14(7-28)38-26)10-3-2-4-13(18(10)21(33)17(11)12(30)6-9)39-27-25(37)23(35)20(32)15(8-29)40-27/h2-6,14-16,19-20,22-32,34-37H,7-8H2,1H3/t14-,15-,16+,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1

> <INCHI_KEY>
GQPFUOPPYJYZHE-ZHVWOXMGSA-N

> <FORMULA>
C27H32O13

> <MOLECULAR_WEIGHT>
564.54

> <EXACT_MASS>
564.18429109

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.26318952363941

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.2223072110000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.053924206712676

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.79525993771621

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6259002805282368

> <JCHEM_POLAR_SURFACE_AREA>
226.82999999999996

> <JCHEM_REFRACTIVITY>
134.1628

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(10S)-1-hydroxy-3-methyl-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10H-anthracen-9-one

> <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       9.336  -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  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   40  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   39                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   21                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    9   22   38                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   27   37                                                  
CONECT   37   36                                                            
CONECT   38   25   21   39                                                  
CONECT   39   38    6   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₃

Average Mass

564.5400 Da

Monoisotopic Mass

564.18429 Da

IUPAC Name

(10S)-1-hydroxy-3-methyl-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-9-one

Traditional Name

(10S)-1-hydroxy-3-methyl-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-10H-anthracen-9-one

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=CC=C3[C@H]([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C2=C1

InChI Identifier

InChI=1S/C27H32O13/c1-9-5-11-16(26-24(36)22(34)19(31)14(7-28)38-26)10-3-2-4-13(18(10)21(33)17(11)12(30)6-9)39-27-25(37)23(35)20(32)15(8-29)40-27/h2-6,14-16,19-20,22-32,34-37H,7-8H2,1H3/t14-,15-,16+,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1

InChI Key

GQPFUOPPYJYZHE-ZHVWOXMGSA-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
Rheum australe	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Anthracene
C-glycosyl compound
O-glycosyl compound
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Benzenoid
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthracenes (CHEBI:80738 )
Anthrone type (C16801 )

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	-1.2	ChemAxon
pKa (Strongest Acidic)	8.8	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	226.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.16 m³·mol⁻¹	ChemAxon
Polarizability	55.26 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

C00031651

Chemspider ID

30791741

KEGG Compound ID

C16801

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173832

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1851431

References

General References

Krenn L, Pradhan R, Presser A, Reznicek G, Kopp B: Anthrone C-glucosides from Rheum emodi. Chem Pharm Bull (Tokyo). 2004 Apr;52(4):391-3. doi: 10.1248/cpb.52.391. [PubMed:15056949 ]
LOTUS database [Link]

Showing NP-Card for cascaroside c (NP0213810)

MOL for NP0213810 (cascaroside c)

3D MOL for NP0213810 (cascaroside c)

3D SDF for NP0213810 (cascaroside c)

3D-SDF for NP0213810 (cascaroside c)

PDB for NP0213810 (cascaroside c)

3D PDB for NP0213810 (cascaroside c)

SMILES for NP0213810 (cascaroside c)

INCHI for NP0213810 (cascaroside c)

Structure for NP0213810 (cascaroside c)

3D Structure for NP0213810 (cascaroside c)