NP-MRD: Showing NP-Card for cassiaoccidentalin b (NP0147654)

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Record Information

Version

2.0

Created at

2022-09-02 03:18:10 UTC

Updated at

2022-09-02 03:18:11 UTC

NP-MRD ID

NP0147654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cassiaoccidentalin b

Description

Cassiaoccidentalin B belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, cassiaoccidentalin b is considered to be a flavonoid. Cassiaoccidentalin B is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. cassiaoccidentalin b is found in Mimosa pudica and Senna occidentalis. cassiaoccidentalin b was first documented in 2016 (PMID: 26702504). Based on a literature review a small amount of articles have been published on cassiaoccidentalin B (PMID: 35492478) (PMID: 34329713) (PMID: 33520796).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205182D          

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M  END

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  Mrv1652309022205182D          

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  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  2  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 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
 28 36  1  0  0  0  0
 36 37  1  6  0  0  0
 26 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
  2 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0147654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@H](O[C@@H](C)[C@H](O)C2=O)C2=C(O)C=C3OC(=CC(=O)C3=C2O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O14/c1-8-20(33)23(36)26(41-27-24(37)22(35)19(32)9(2)39-27)25(38-8)18-14(31)7-16-17(21(18)34)13(30)6-15(40-16)10-3-4-11(28)12(29)5-10/h3-9,19-20,22,24-29,31-35,37H,1-2H3/t8-,9-,19-,20-,22+,24+,25+,26-,27-/m0/s1

> <INCHI_KEY>
WGIMZJFXUGTVFX-RUYCBFJTSA-N

> <FORMULA>
C27H28O14

> <MOLECULAR_WEIGHT>
576.507

> <EXACT_MASS>
576.147905582

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
55.69178443847444

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3R,5S,6S)-5-hydroxy-6-methyl-4-oxo-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
0.5839633689999998

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.707441480082289

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.134220943501672

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121828723554428

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999995

> <JCHEM_REFRACTIVITY>
136.57230000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3R,5S,6S)-5-hydroxy-6-methyl-4-oxo-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   0.000   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       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334  -5.390   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       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   11   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    9   24                                                  
CONECT   24   23    5   25                                                  
CONECT   25   24                                                            
CONECT   26    4   27   38                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   28   37                                                  
CONECT   37   36                                                            
CONECT   38   26   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38    2   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

C₂₇H₂₈O₁₄

Average Mass

576.5070 Da

Monoisotopic Mass

576.14791 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3R,5S,6S)-5-hydroxy-6-methyl-4-oxo-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2R,3R,5S,6S)-5-hydroxy-6-methyl-4-oxo-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]chromen-4-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@H](O[C@@H](C)[C@H](O)C2=O)C2=C(O)C=C3OC(=CC(=O)C3=C2O)C2=CC=C(O)C(O)=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H28O14/c1-8-20(33)23(36)26(41-27-24(37)22(35)19(32)9(2)39-27)25(38-8)18-14(31)7-16-17(21(18)34)13(30)6-15(40-16)10-3-4-11(28)12(29)5-10/h3-9,19-20,22,24-29,31-35,37H,1-2H3/t8-,9-,19-,20-,22+,24+,25+,26-,27-/m0/s1

InChI Key

WGIMZJFXUGTVFX-RUYCBFJTSA-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
Mimosa pudica	LOTUS Database	35616633
Senna occidentalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Glycosyl compound
O-glycosyl compound
Chromone
1-benzopyran
Benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Vinylogous acid
Heteroaromatic compound
Cyclic ketone
Secondary alcohol
Ketone
Dialkyl ether
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Ether
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:70205 )
tetrahydroxyflavone (CHEBI:70205 )
flavone C-glycoside (CHEBI:70205 )

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	1.44	ALOGPS
logP	0.58	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.13	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	232.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.57 m³·mol⁻¹	ChemAxon
Polarizability	55.69 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

C00014065

Chemspider ID

34448464

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70698280

PDB ID

Not Available

ChEBI ID

70205

Good Scents ID

Not Available

References

General References

Dwivedi PSR, Patil R, Khanal P, Gurav NS, Murade VD, Hase DP, Kalaskar MG, Ayyanar M, Chikhale RV, Gurav SS: Exploring the therapeutic mechanisms of Cassia glauca in diabetes mellitus through network pharmacology, molecular docking and molecular dynamics. RSC Adv. 2021 Dec 9;11(62):39362-39375. doi: 10.1039/d1ra07661b. eCollection 2021 Dec 6. [PubMed:35492478 ]
Borges PHO, Pedreiro S, Baptista SJ, Geraldes CFGC, Batista MT, Silva MMC, Figueirinha A: Inhibition of alpha-glucosidase by flavonoids of Cymbopogon citratus (DC) Stapf. J Ethnopharmacol. 2021 Nov 15;280:114470. doi: 10.1016/j.jep.2021.114470. Epub 2021 Jul 27. [PubMed:34329713 ]
Ternikar SG, Patil MB, Pasha I, Khanal P: Gene set enrichment analysis of alpha-amylase and alpha-glucosidase inhibitors of Cassia glauca. J Diabetes Metab Disord. 2020 May 28;19(2):683-689. doi: 10.1007/s40200-020-00538-9. eCollection 2020 Dec. [PubMed:33520796 ]
Costa G, Ferreira JP, Vitorino C, Pina ME, Sousa JJ, Figueiredo IV, Batista MT: Polyphenols from Cymbopogon citratus leaves as topical anti-inflammatory agents. J Ethnopharmacol. 2016 Feb 3;178:222-8. doi: 10.1016/j.jep.2015.12.016. Epub 2015 Dec 17. [PubMed:26702504 ]
LOTUS database [Link]

Showing NP-Card for cassiaoccidentalin b (NP0147654)

MOL for NP0147654 (cassiaoccidentalin b)

3D MOL for NP0147654 (cassiaoccidentalin b)

3D SDF for NP0147654 (cassiaoccidentalin b)

3D-SDF for NP0147654 (cassiaoccidentalin b)

PDB for NP0147654 (cassiaoccidentalin b)

3D PDB for NP0147654 (cassiaoccidentalin b)

SMILES for NP0147654 (cassiaoccidentalin b)

INCHI for NP0147654 (cassiaoccidentalin b)

Structure for NP0147654 (cassiaoccidentalin b)

3D Structure for NP0147654 (cassiaoccidentalin b)