NP-MRD: Showing NP-Card for Orientin (NP0044881)

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Record Information

Version

2.0

Created at

2022-03-10 18:37:08 UTC

Updated at

2022-03-10 22:21:57 UTC

NP-MRD ID

NP0044881

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orientin

Description

Orientin, also known as lutexin, is an 8-C-glycosilated derivative of the flavonoid luteolin, substituted by beta-D-glucopyranosyl. Flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C; also shared by the tocopherols), with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. 8-C-glycosilated flavonoids are compounds containing a carbohydrate moiety which is C-glycosidically linked to position 8 of a 2-phenylchromen-4-one flavonoid backbone. Orientin is a neutral compound. Orientin is a water-soluble flavonoid C-glycoside found in calcium tree, black bamboo, spelts, triticales, red rices, hard wheats, flaxseeds, wild apricot and cucumber; in barley, flax and tamarind leaves; in basil, blueberry, oregano plants; passion flower, the¬¨‚Ä†A‚àö√üa‚àö‚â† palm,¬¨‚Ä†buckwheat¬¨‚Ä†sprouts,¬¨‚Ä†and in¬¨‚Ä†millets. It is one of several dozen flavonoid glycosides that have been identified in low-THC Cannabis cultivars (PMID: 6991645 ). Flavonoids are polyphenolic compounds that are universally present as constituents of flowering plants, particularly of food plants. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. Orientin, extracted from different medicinal plants, exhibits antioxidant, anti-aging, anti-viral, anti-bacterial, anti-inflammation, vasodilatation and cardioprotective, radiation protective, neuroprotective, antidepressant-like, anti-adipogenesis, and anti-nociceptive effects that have been reviewed (PMID: 27298620 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

5281675
  Mrv1652303202019012D          

 33 36  0  0  1  0            999 V2000
    4.2365   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740    0.3839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9645    2.9161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 31 32  1  0  0  0  0
M  END

     RDKit          3D

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   -1.1036   -0.7550   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6352   -1.4196    0.5245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3437   -0.6522    1.4912 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6851   -1.3080    1.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917   -2.6369    2.1321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5117    0.7368    0.9417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3384    1.5519    1.7084 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7957    0.2492    2.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0129   -0.3122   -5.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
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  7 35  1  0
  6 34  1  0
M  END

5281675
  Mrv1652303202019012D          

 33 36  0  0  1  0            999 V2000
    4.2365   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9740    0.3839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.8876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9645    2.9161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1409   -1.6727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5731   -0.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8075   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5220   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0044881

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1

> <INCHI_KEY>
PLAPMLGJVGLZOV-VPRICQMDSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.3769

> <EXACT_MASS>
448.100561482

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.37645504711216

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
-0.35419709299999974

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.9970769399637565

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.172660635500586

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791926292654134

> <JCHEM_POLAR_SURFACE_AREA>
197.36999999999998

> <JCHEM_REFRACTIVITY>
108.01309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orientin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5281675                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  O   UNK     0       7.908  -1.540   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907  -0.770   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.574  -5.390   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.285   0.717   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.242  -5.390   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.907   0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.574   5.390   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.267   5.443   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      13.330  -3.122   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      16.003  -1.592   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.241  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.241  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.908  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.242  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.908   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.241   3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.574   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.285   3.904   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.680   1.508   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.680   3.112   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.011   0.733   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.005  -0.807   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.348   1.498   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.336  -1.582   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.678   0.723   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.672  -0.817   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0       7.708  -0.116   0.000  0.00  0.00           H+0
CONECT    1   14   16                                                       
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   15                                                            
CONECT    5   19   25                                                       
CONECT    6   18                                                            
CONECT    7   20                                                            
CONECT    8   23                                                            
CONECT    9   24                                                            
CONECT   10   30                                                            
CONECT   11   32                                                            
CONECT   12    2   13   14                                                  
CONECT   13    3   12   15                                                  
CONECT   14    1   12   17   33                                             
CONECT   15    4   13   16                                                  
CONECT   16    1   15   18                                                  
CONECT   17   14   19   20                                                  
CONECT   18    6   16                                                       
CONECT   19    5   17   21                                                  
CONECT   20    7   17   22                                                  
CONECT   21   19   23   24                                                  
CONECT   22   20   23                                                       
CONECT   23    8   21   22                                                  
CONECT   24    9   21   26                                                  
CONECT   25    5   26   27                                                  
CONECT   26   24   25                                                       
CONECT   27   25   28   29                                                  
CONECT   28   27   30                                                       
CONECT   29   27   31                                                       
CONECT   30   10   28   32                                                  
CONECT   31   29   32                                                       
CONECT   32   11   30   31                                                  
CONECT   33   14                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
8-beta-D-Glucosylluteolin	ChEBI
Luteolin 8-C-glucoside	ChEBI
Lutexin	ChEBI
8-b-D-Glucosylluteolin	Generator
8-Β-D-glucosylluteolin	Generator
8-C-beta-Glucopyranosyl-3',4',5,7-tetrahydroxyflav-2-en-3-one	MeSH

Chemical Formula

C₂₁H₂₀O₁₁

Average Mass

448.3769 Da

Monoisotopic Mass

448.10056 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

orientin

CAS Registry Number

28608-75-5

SMILES

[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1

InChI Key

PLAPMLGJVGLZOV-VPRICQMDSA-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
Acer palmatum	LOTUS Database	35616633
Achillea nobilis	LOTUS Database	35616633
Adenocarpus artemisiifolius	LOTUS Database	35616633
Aeluropus lagopoides	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Arum maculatum	LOTUS Database	35616633
Ascarina lucida	Plant	KNApSAcK
Aspalathus linearis	LOTUS Database	35616633
Cajanus cajan	LOTUS Database	35616633
Calicotome villosa	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Carallia brachiata	LOTUS Database	35616633
Carlina macrocephala	LOTUS Database	35616633
Cecropia glaziovii	LOTUS Database	35616633
Cecropia pachystachya	LOTUS Database	35616633
Centaurea gigantea	Plant	KNApSAcK
Centaurea horrida	LOTUS Database	35616633
Centaurea melitensis L.	Plant	KNApSAcK
Centaurea pseudomaculosa	LOTUS Database	35616633
Centaurea solstitialis	Plant	KNApSAcK
Cinnamomum verum	LOTUS Database	35616633
Clinacanthus nutans	Plant	KNApSAcK
Colocasia esculenta	Plant	KNApSAcK
Colocasia escultenta	Plant	KNApSAcK
Combretum micranthum	LOTUS Database	35616633
Commelina communis L	Plant	KNApSAcK
Crataegus monogyna	LOTUS Database	35616633
Crossopteryx febrifuga	LOTUS Database	35616633
Crotalaria sessiliflora	LOTUS Database	35616633
Cucumis sativus	LOTUS Database	35616633
Cucumis sativus L.	FooDB	KNAPSACK
Cyathea spp.	Plant	KNApSAcK
Cymbopogon citratus	Plant	KNApSAcK
Cyperus alopecuroides	Plant	KNApSAcK
Cytisus hirsutus	LOTUS Database	35616633
Dactylis glomerata	LOTUS Database	35616633
Daphne gnidium	LOTUS Database	35616633
Daphne laureola	LOTUS Database	35616633
Deschampsia antarctica	LOTUS Database	35616633
Desmodium canadense	LOTUS Database	35616633
Dianthus arenarius	LOTUS Database	35616633
Drosophyllum lusitanicum	LOTUS Database	35616633
Eleutherococcus brachypus	LOTUS Database	35616633
Eremochloa ophiuroides	LOTUS Database	35616633
Euphorbia supina Rafin	Plant	KNApSAcK
Fagopyrum esculentum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ficaria verna	LOTUS Database	35616633
Gaillardia aristata	LOTUS Database	35616633
Gaillardia pulchella	LOTUS Database	35616633
Gentiana algida	LOTUS Database	35616633
Gleditsia sinensis	Plant	KNApSAcK
Gypsophila paniculata	LOTUS Database	35616633
Heterotis rotundifolia	LOTUS Database	35616633
Hordeum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hyparrhenia hirta	LOTUS Database	35616633
Iris ensata	LOTUS Database	35616633
Isodon rubescens var. lushanensis	Plant	KNApSAcK
Itea yunnanensis	LOTUS Database	35616633
Itoa orientalis	LOTUS Database	35616633
Japonolirion osense	Plant	KNApSAcK
Lamyropsis cynaroides	LOTUS Database	35616633
Lepisorus ussuriensis	LOTUS Database	35616633
Lespedeza bicolor	Plant	KNApSAcK
Lespedeza hedysaroides	Plant	KNApSAcK
Lespedeza juncea	LOTUS Database	35616633
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lupinus polyphyllus	LOTUS Database	35616633
Lupinus texensis	LOTUS Database	35616633
Lychnis flos-cuculi L.	Plant	KNApSAcK
Lythrum salicaria	Plant	KNApSAcK
Melanargia galathea	LOTUS Database	35616633
Melilotus indica	LOTUS Database	35616633
Mimosa pudica	LOTUS Database	35616633
Moraea sisyrinchium	LOTUS Database	35616633
Musanga cecropioides	LOTUS Database	35616633
Nymphaea alba	Plant	KNApSAcK
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ocimum tenuiflorum	LOTUS Database	35616633
Oenothera canescens	LOTUS Database	35616633
Oenothera macrocarpa	LOTUS Database	35616633
Origanum majorana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Papaver orientale	LOTUS Database	35616633
Parkinsonia aculeata	Plant	KNApSAcK
Passiflora alata	LOTUS Database	35616633
Passiflora colinvauxii	LOTUS Database	35616633
Passiflora incarnata	Plant	KNApSAcK
Passiflora menispermifolia	LOTUS Database	35616633
Passiflora serratifolia	LOTUS Database	35616633
Passiflora serratodigitata	Plant	KNApSAcK
Passiflora sexflora	LOTUS Database	35616633
Pelargonium reniforme	Plant	KNApSAcK
Pelargonium sidoides	Plant	KNApSAcK
Pennisetum americanum	Plant	KNApSAcK
Phlomoides tuberosa	LOTUS Database	35616633
Phoenix loureiroi	LOTUS Database	35616633
Piper solmsianum	LOTUS Database	35616633
Pistia stratiotes	LOTUS Database	35616633
Poa annua	LOTUS Database	35616633
Podocarpus fasciculus	Plant	KNApSAcK
Podocarpus nivalis	LOTUS Database	35616633
Polygonum orientale	Plant	KNApSAcK
Primula veris	Plant	KNApSAcK
Ranunculus illyricus	LOTUS Database	35616633
Retama raetam	Plant	KNApSAcK
Retama sphaerocarpa	LOTUS Database	35616633
Rhamnus davurica	Plant	KNApSAcK
Rhynchosia beddomei	LOTUS Database	35616633
Rumex acetosa	LOTUS Database	35616633
Rumex vesicarius	LOTUS Database	35616633
Saccharum officinarum	LOTUS Database	35616633
Scutellaria albida	LOTUS Database	35616633
Setaria italica	LOTUS Database	35616633
Sigesbeckia orientalis	-	KNApSAcK
Silene saxatilis	LOTUS Database	35616633
Silene spp.	Plant	KNApSAcK
Stellaria holostea	Plant	KNApSAcK
Stellaria media	LOTUS Database	35616633
Stellaria nemorum	Plant	KNApSAcK
Tamarindus indica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tanacetum vulgare	LOTUS Database	35616633
Taxus chinensis	Plant	KNApSAcK
Telephium imperati	LOTUS Database	35616633
Terminalia brachystemma	LOTUS Database	35616633
Terminalia myriocarpa	LOTUS Database	35616633
Thalictrum minus	LOTUS Database	35616633
Theobroma cacao	Plant	KNApSAcK
Tinospora crispa	LOTUS Database	35616633
Tragopogon porrifolius	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tragopogon pratensis	LOTUS Database	35616633
Trichomanes holopterum	LOTUS Database	35616633
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trigonella grandiflora	LOTUS Database	35616633
Trollius chinensis	Plant	KNApSAcK
Trollius ledebouri	Plant	KNApSAcK
Trollius macropetalus	Plant	KNApSAcK
Turnera diffusa	Plant	KNApSAcK
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vellozia epidendroides	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Vitex cannabifolia Sieb.et.Zucc.	Plant	KNApSAcK
Vitex negundo	LOTUS Database	35616633
Vitex polygama	Plant	KNApSAcK
Vitis aestivalis	LOTUS Database	35616633
Wilbrandia ebracteata	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
C-glycosyl compound
Chromone
1-benzopyran
Benzopyran
Catechol
Phenol
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-glycosyl compound (CHEBI:7781 )
tetrahydroxyflavone (CHEBI:7781 )
3'-hydroxyflavonoid (CHEBI:7781 )
flavones (C10114 )
Flavones and Flavonols (C10114 )

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	0.34	ALOGPS
logP	-0.35	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	197.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	108.01 m³·mol⁻¹	ChemAxon
Polarizability	42.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00001078

Chemspider ID

Not Available

KEGG Compound ID

C10114

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Orientin

METLIN ID

Not Available

PubChem Compound

5281675

PDB ID

Not Available

ChEBI ID

7781

Good Scents ID

Not Available

References

General References

Lam KY, Ling AP, Koh RY, Wong YP, Say YH: A Review on Medicinal Properties of Orientin. Adv Pharmacol Sci. 2016;2016:4104595. doi: 10.1155/2016/4104595. Epub 2016 May 19. [PubMed:27298620 ]
Lu N, Sun Y, Zheng X: Orientin-induced cardioprotection against reperfusion is associated with attenuation of mitochondrial permeability transition. Planta Med. 2011 Jul;77(10):984-91. doi: 10.1055/s-0030-1250718. Epub 2011 Jan 31. [PubMed:21283956 ]
Kim HJ, Park KJ, Lim JH: Metabolomic analysis of phenolic compounds in buckwheat (Fagopyrum esculentum M.) sprouts treated with methyl jasmonate. J Agric Food Chem. 2011 May 25;59(10):5707-13. doi: 10.1021/jf200396k. Epub 2011 Apr 1. [PubMed:21417394 ]
Mali VR, Mohan V, Bodhankar SL: Antihypertensive and cardioprotective effects of the Lagenaria siceraria fruit in NG-nitro-L-arginine methyl ester (L-NAME) induced hypertensive rats. Pharm Biol. 2012 Nov;50(11):1428-35. doi: 10.3109/13880209.2012.684064. Epub 2012 Sep 21. [PubMed:22994444 ]
Khan RA: Evaluation of flavonoids and diverse antioxidant activities of Sonchus arvensis. Chem Cent J. 2012 Oct 29;6(1):126. doi: 10.1186/1752-153X-6-126. [PubMed:23107458 ]
Simirgiotis MJ, Schmeda-Hirschmann G, Borquez J, Kennelly EJ: The Passiflora tripartita (Banana Passion) fruit: a source of bioactive flavonoid C-glycosides isolated by HSCCC and characterized by HPLC-DAD-ESI/MS/MS. Molecules. 2013 Jan 28;18(2):1672-92. doi: 10.3390/molecules18021672. [PubMed:23358325 ]

Showing NP-Card for Orientin (NP0044881)

MOL for NP0044881 (Orientin)

3D MOL for NP0044881 (Orientin)

3D SDF for NP0044881 (Orientin)

3D-SDF for NP0044881 (Orientin)

PDB for NP0044881 (Orientin)

3D PDB for NP0044881 (Orientin)

SMILES for NP0044881 (Orientin)

INCHI for NP0044881 (Orientin)

Structure for NP0044881 (Orientin)

3D Structure for NP0044881 (Orientin)