NP-MRD: Showing NP-Card for Taxifolin 3-rhamnoside (NP0047765)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:36 UTC

Updated at

2022-03-17 20:45:36 UTC

NP-MRD ID

NP0047765

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taxifolin 3-rhamnoside

Description

Astilbin belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Astilbin is a flavanonol, a type of flavonoid. Astilbin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Astilbin is found, on average, in the highest concentration within grape wines. Astilbin has also been detected, but not quantified in, a few different foods, such as alcoholic beverages, common grapes, and fruits. This could make astilbin a potential biomarker for the consumption of these foods. Taxifolin 3-rhamnoside is found in Andira inermis, Astilbe thunbergii, Bicuiba oleifera, Calliandra haematocephala, Cratoxylum arborescens, Cratoxylum formosum, Desmos cochinchinensis, Dimorphandra mollis, Drimys granadensis, Drimys winteri, Engelhardtia chrysolepis, Garcinia mangostana, Harungana madagascariensis, Hymenaea martiana, Hymenaea parvifolia, Hypericum patulum, Hypericum perforatum, Iryanthera sagotiana, Litsea sericea, Lyonia ovalifolia, Mallotus metcalfianus, Malpighia emarginata, Petiveria alliacea, Rhododendron simsii, Sarcandra glabra, Smilax corbularia, Smilax glabra, Sphaerostephanos arbuscula, Stelechocarpus cauliflorus and Vitis vinifera. Taxifolin 3-rhamnoside was first documented in 2010 (PMID: 21157633). It can be found in St John's wort (Hypericum perforatum, Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in Dimorphandra mollis (Fava d'anta, Fabaceae), in the the leaves of Harungana madagascariensis (Hypericaceae), in the rhizome of Astilbe thunbergii, in the root of Astilbe odontophylla(Saxifragaceae) and in the rhizone of Smilax glabra (Chinaroot, Smilacaceae) (PMID: 21476602) (PMID: 21600261) (PMID: 21614752).

Structure

MOL SDF PDB SMILES InChI

Dihydroquercetin 3-O-rhamnoside
  Mrv1652309281722592D          

 32 35  0  0  1  0            999 V2000
   -0.1786   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5358   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503   -2.4749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2503   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358   -1.2374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5358   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1786    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6791   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6791   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2503   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END

Dihydroquercetin 3-O-rhamnoside
  Mrv1652309281722592D          

 32 35  0  0  1  0            999 V2000
   -0.1786   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5358   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503   -2.4749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2503   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5358   -1.2374    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5358   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1786    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0365    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6076   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8931   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6791   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9648   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6791   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2503   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2503   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
  4 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0047765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1

> <INCHI_KEY>
ZROGCCBNZBKLEL-MPRHSVQHSA-N

> <FORMULA>
C21H22O11

> <MOLECULAR_WEIGHT>
450.3928

> <EXACT_MASS>
450.116211546

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.85745817441533

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
0.79

> <JCHEM_LOGP>
1.0924585889999998

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.000676709656753

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.741338554809933

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612182875000423

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
105.47849999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
astilbin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Dihydroquercetin 3-O-rhamnoside                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-SEP-17         0                                  
HETATM    1  C   UNK     0      -0.333  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.000  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.000  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.334  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.334  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.000  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.000  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.333   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.667  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.001   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.335  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.668   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.335  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.001  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.001  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.667  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.333  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.333  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.334   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.001   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.335  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.001   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.335   2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.334   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.001  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.668  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.001  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.334  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.334  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16    6   18                                                  
CONECT   18   17                                                            
CONECT   19    7   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19                                                       
CONECT   27    4   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one	ChEBI
(2R,3R)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
Dihydroquercetin-3-O-alpha-lrhap	ChEBI
(2R,3R)-3-[(6-Deoxy-a-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one	Generator
(2R,3R)-3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one	Generator
Dihydroquercetin-3-O-a-lrhap	Generator
Dihydroquercetin-3-O-α-lrhap	Generator
Isoastilbin	MeSH
(2R-cis)-Isomer OF astilbin	MeSH
3-0-alpha-1-Rhamnosyl-(2R,3R)-dihydroquercetin	MeSH
Neoisoastilbin	MeSH
(2S-cis)-Isomer OF astilbin	MeSH

Chemical Formula

C₂₁H₂₂O₁₁

Average Mass

450.3928 Da

Monoisotopic Mass

450.11621 Da

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

astilbin

CAS Registry Number

29838-67-3

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@H](OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1

InChI Key

ZROGCCBNZBKLEL-MPRHSVQHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Andira inermis	LOTUS Database	35616633
Astilbe thunbergii	LOTUS Database	35616633
Bicuiba oleifera	LOTUS Database	35616633
Calliandra haematocephala	LOTUS Database	35616633
Cratoxylum arborescens	LOTUS Database	35616633
Cratoxylum formosum	LOTUS Database	35616633
Desmos cochinchinensis	LOTUS Database	35616633
Dimorphandra mollis	LOTUS Database	35616633
Drimys granadensis	LOTUS Database	35616633
Drimys winteri	LOTUS Database	35616633
Engelhardtia chrysolepis	Plant	KNApSAcK
Garcinia mangostana	LOTUS Database	35616633
Harungana madagascariensis	LOTUS Database	35616633
Hymenaea martiana	LOTUS Database	35616633
Hymenaea parvifolia	LOTUS Database	35616633
Hypericum patulum	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Iryanthera sagotiana	LOTUS Database	35616633
Litsea sericea	LOTUS Database	35616633
Lyonia ovalifolia	LOTUS Database	35616633
Mallotus metcalfianus	LOTUS Database	35616633
Malpighia emarginata	LOTUS Database	35616633
Petiveria alliacea	LOTUS Database	35616633
Rhododendron simsii	LOTUS Database	35616633
Sarcandra glabra	LOTUS Database	35616633
Smilax corbularia	LOTUS Database	35616633
Smilax glabra	LOTUS Database	35616633
Sphaerostephanos arbuscula	-	KNApSAcK
Stelechocarpus cauliflorus	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Hydroxyflavonoid
Flavanonol
Flavanone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Flavan
Hexose monosaccharide
Chromone
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Secondary alcohol
Ketone
Ether
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:38200 )
3'-hydroxyflavanones (CHEBI:38200 )
alpha-L-rhamnoside (CHEBI:38200 )
flavanone glycoside (CHEBI:38200 )
tetrahydroxyflavanone (CHEBI:38200 )

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	0.79	ALOGPS
logP	1.09	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	105.48 m³·mol⁻¹	ChemAxon
Polarizability	42.86 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

HMDB0033850

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Astilbin

METLIN ID

Not Available

PubChem Compound

119258

PDB ID

Not Available

ChEBI ID

38200

Good Scents ID

Not Available

References

General References

Petacci F, Freitas SS, Brunetti IL, Khalil NM: Inhibition of peroxidase activity and scavenging of reactive oxygen species by astilbin isolated from Dimorphandra mollis (Fabaceae, Caesalpinioideae). Biol Res. 2010;43(1):63-74. doi: /S0716-97602010000100008. Epub 2010 May 7. [PubMed:21157633 ]
Huang H, Cheng Z, Shi H, Xin W, Wang TT, Yu LL: Isolation and characterization of two flavonoids, engeletin and astilbin, from the leaves of Engelhardia roxburghiana and their potential anti-inflammatory properties. J Agric Food Chem. 2011 May 11;59(9):4562-9. doi: 10.1021/jf2002969. Epub 2011 Apr 19. [PubMed:21476602 ]
Huang J, Wang S, Zhu M, Chen J, Zhu X: Effects of genistein, apigenin, quercetin, rutin and astilbin on serum uric acid levels and xanthine oxidase activities in normal and hyperuricemic mice. Food Chem Toxicol. 2011 Sep;49(9):1943-7. doi: 10.1016/j.fct.2011.04.029. Epub 2011 May 10. [PubMed:21600261 ]
Chen L, Lan Z, Zhou Y, Li F, Zhang X, Zhang C, Yang Z, Li P: Astilbin attenuates hyperuricemia and ameliorates nephropathy in fructose-induced hyperuricemic rats. Planta Med. 2011 Nov;77(16):1769-73. doi: 10.1055/s-0030-1271135. Epub 2011 May 25. [PubMed:21614752 ]

Showing NP-Card for Taxifolin 3-rhamnoside (NP0047765)

MOL for NP0047765 (Taxifolin 3-rhamnoside)

3D MOL for NP0047765 (Taxifolin 3-rhamnoside)

3D SDF for NP0047765 (Taxifolin 3-rhamnoside)

3D-SDF for NP0047765 (Taxifolin 3-rhamnoside)

PDB for NP0047765 (Taxifolin 3-rhamnoside)

3D PDB for NP0047765 (Taxifolin 3-rhamnoside)

SMILES for NP0047765 (Taxifolin 3-rhamnoside)

INCHI for NP0047765 (Taxifolin 3-rhamnoside)

Structure for NP0047765 (Taxifolin 3-rhamnoside)

3D Structure for NP0047765 (Taxifolin 3-rhamnoside)