NP-MRD: Showing NP-Card for Cascaroside A (NP0051591)

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Record Information

Version

2.0

Created at

2022-04-27 22:53:56 UTC

Updated at

2022-04-27 22:53:56 UTC

NP-MRD ID

NP0051591

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cascaroside A

Description

Cascaroside a 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. Thus, cascaroside a is considered to be an aromatic polyketide. Cascaroside A is found in Rhamnus purshiana . Based on a literature review very few articles have been published on Cascaroside a.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200542D          

 41 45  0  0  1  0            999 V2000
    4.2868    0.8250    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
    3.5724   -0.4125    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  4  5  1  0  0  0  0
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  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
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 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
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 21 38  1  0  0  0  0
 38 39  1  0  0  0  0
 36 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282200542D          

 41 45  0  0  1  0            999 V2000
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    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 11 16  1  6  0  0  0
 10 17  1  1  0  0  0
  9 18  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  1  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 27 32  1  6  0  0  0
 26 33  1  1  0  0  0
 25 34  1  6  0  0  0
 22 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 21 38  1  0  0  0  0
 38 39  1  0  0  0  0
 36 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051591

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C3C(=O)C4=C(C=C(CO)C=C4O)[C@@H]([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C3=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O14/c28-6-9-4-11-16(26-24(37)22(35)19(32)14(7-29)39-26)10-2-1-3-13(18(10)21(34)17(11)12(31)5-9)40-27-25(38)23(36)20(33)15(8-30)41-27/h1-5,14-16,19-20,22-33,35-38H,6-8H2/t14-,15-,16+,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1

> <INCHI_KEY>
MNAYRSRTNMVAPR-ZHVWOXMGSA-N

> <FORMULA>
C27H32O14

> <MOLECULAR_WEIGHT>
580.539

> <EXACT_MASS>
580.17920571

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.37668389796091

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10S)-1-hydroxy-3-(hydroxymethyl)-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

> <ALOGPS_LOGP>
-1.24

> <JCHEM_LOGP>
-2.5030783676666672

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.05386518212807

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.53116127310234

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6259002864570977

> <JCHEM_POLAR_SURFACE_AREA>
247.05999999999997

> <JCHEM_REFRACTIVITY>
135.93749999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cascaroside A

> <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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    9                                                            
CONECT   19    5   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   38                                                  
CONECT   22   21   23   35                                                  
CONECT   23   22    4   24                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   34                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   27                                                            
CONECT   33   26                                                            
CONECT   34   25                                                            
CONECT   35   22   36                                                       
CONECT   36   35   37   40                                                  
CONECT   37   36   38                                                       
CONECT   38   37   21   39                                                  
CONECT   39   38                                                            
CONECT   40   36   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₄

Average Mass

580.5390 Da

Monoisotopic Mass

580.17921 Da

IUPAC Name

(10S)-1-hydroxy-3-(hydroxymethyl)-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

cascaroside A

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C3C(=O)C4=C(C=C(CO)C=C4O)[C@@H]([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C3=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H32O14/c28-6-9-4-11-16(26-24(37)22(35)19(32)14(7-29)39-26)10-2-1-3-13(18(10)21(34)17(11)12(31)5-9)40-27-25(38)23(36)20(33)15(8-30)41-27/h1-5,14-16,19-20,22-33,35-38H,6-8H2/t14-,15-,16+,19-,20-,22+,23+,24-,25-,26+,27-/m1/s1

InChI Key

MNAYRSRTNMVAPR-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, 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
Rhamnus purshiana	Plant	KNApSAcK

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
Aromatic alcohol
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthracenes (CHEBI:3446 )
Anthracenes and phenanthrenes (C10307 )
Anthrone type (C10307 )
Anthracenes and phenanthrenes (LMPK13040003 )

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	ALOGPS
logP	-2.5	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.53	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	247.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	135.94 m³·mol⁻¹	ChemAxon
Polarizability	56.38 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002799

Chemspider ID

391075

KEGG Compound ID

C10307

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442727

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1667111

References

General References

Not Available

Showing NP-Card for Cascaroside A (NP0051591)

MOL for NP0051591 (Cascaroside A)

3D MOL for NP0051591 (Cascaroside A)

3D SDF for NP0051591 (Cascaroside A)

3D-SDF for NP0051591 (Cascaroside A)

PDB for NP0051591 (Cascaroside A)

3D PDB for NP0051591 (Cascaroside A)

SMILES for NP0051591 (Cascaroside A)

INCHI for NP0051591 (Cascaroside A)

Structure for NP0051591 (Cascaroside A)

3D Structure for NP0051591 (Cascaroside A)