NP-MRD: Showing NP-Card for scutellarin (NP0224779)

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Record Information

Version

2.0

Created at

2022-09-06 03:17:57 UTC

Updated at

2022-09-06 03:17:57 UTC

NP-MRD ID

NP0224779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

scutellarin

Description

Scutellarin belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Thus, scutellarin is considered to be a flavonoid. scutellarin is found in Ageratum conyzoides, Clerodendrum indicum, Erigeron breviscapus, Galeopsis bifida, Monarda punctata, Oroxylum indicum, Perilla frutescens, Portulaca oleracea, Scoparia dulcis, Scutellaria alpina, Scutellaria barbata, Scutellaria indica, Scutellaria lateriflora, Sempervivum ruthenicum and Tripora divaricata. scutellarin was first documented in 2022 (PMID: 36036213). Based on a literature review a significant number of articles have been published on scutellarin (PMID: 36032701) (PMID: 36017831) (PMID: 36017130) (PMID: 35964195) (PMID: 35915209) (PMID: 35850795).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062205172D          

 33 36  0  0  1  0            999 V2000
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 12 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
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  8 26  2  0  0  0  0
 26 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -6.1722   -1.6543    2.6768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2539   -1.6200    1.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0465   -2.7689    1.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4414   -0.3772    1.6298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5254   -0.6481    0.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710    0.3541    0.4673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1576    0.3103   -0.8766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9072    0.1754   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860    0.0565   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4710   -0.0822   -1.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862   -0.1926   -0.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7302   -0.3269   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8130   -0.4448    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1300   -0.5870    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1261   -0.6955    0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7929   -0.6603    2.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7606   -0.7657    3.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4674   -0.5171    2.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4838   -0.4101    1.6883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9821   -0.3532   -2.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -0.2411   -2.9351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1736   -0.2642   -4.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724   -0.1030   -2.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650    0.0174   -3.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640    0.0077   -4.6667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7087    0.1548   -2.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790    0.2713   -3.6075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976    1.6947    0.6355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4235    2.0323    1.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6965    1.4833    0.0933 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6459    0.6417   -1.0184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4410    0.6990    1.1836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6987    1.6018    2.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5801   -3.0486    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9943   -0.1479    2.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7564    0.2655    1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289    0.0619    0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4237   -0.6181   -1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1476   -0.8058    0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1593    0.1146    3.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1665   -0.4853    3.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4387   -0.2972    1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9874   -0.4617   -2.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4157   -0.0733   -5.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    0.2566   -4.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    2.5090    0.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    2.0515    2.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2056    2.4398   -0.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4160    0.0446   -1.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3325    0.2719    0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2977    1.1342    2.8494 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 28  1  0
 28 29  1  0
 28  6  1  0
  6  7  1  0
  7  8  1  0
  8 26  2  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 23  2  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 12  2  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  6  5  1  0
  5  4  1  0
  4 32  1  0
 32 33  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 32 30  1  0
  9  8  1  0
 19 13  1  0
 10 23  1  0
 31 49  1  0
 30 48  1  6
 28 46  1  6
 29 47  1  0
  6 36  1  1
 27 45  1  0
 25 44  1  0
 20 43  1  0
  9 37  1  0
 14 38  1  0
 15 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
  4 35  1  1
 32 50  1  6
 33 51  1  0
  3 34  1  0
M  END


  Mrv1652309062205172D          

 33 36  0  0  1  0            999 V2000
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   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
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 13 19  1  0  0  0  0
 12 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
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
  8 26  2  0  0  0  0
 26 27  1  0  0  0  0
  6 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0224779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](OC2=C(O)C(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)O[C@@H]([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

> <INCHI_KEY>
DJSISFGPUUYILV-ZFORQUDYSA-N

> <FORMULA>
C21H18O12

> <MOLECULAR_WEIGHT>
462.363

> <EXACT_MASS>
462.07982602

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.10433686318916

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_LOGP>
0.4553302566666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.5163148196542044

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6182265954446957

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868279925292358

> <JCHEM_POLAR_SURFACE_AREA>
203.44

> <JCHEM_REFRACTIVITY>
106.90659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
scutellarin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13                                                       
CONECT   20   12   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   10   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    8   27                                                  
CONECT   27   26                                                            
CONECT   28    6   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    4   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Scutellarein 7-O-beta-D-glucuronide	ChEBI
Scutellarein-7-glucuronide	ChEBI
Scutellarein-7-O-beta-D-glucuronide	ChEBI
Scutellarein-7beta-D-glucuronide	ChEBI
Scutellarein-7beta-D-glucuronoside	ChEBI
Scutellarein 7-O-b-D-glucuronide	Generator
Scutellarein 7-O-β-D-glucuronide	Generator
Scutellarein-7-O-b-D-glucuronide	Generator
Scutellarein-7-O-β-D-glucuronide	Generator
Scutellarein-7b-D-glucuronide	Generator
Scutellarein-7β-D-glucuronide	Generator
Scutellarein-7b-D-glucuronoside	Generator
Scutellarein-7β-D-glucuronoside	Generator
Scutellarein 7-beta-D-glucuronoside	MeSH
beta-D-Glucopyranosiduronic acid, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl	MeSH
Scutellarein 7-beta-D-glucuronide	MeSH
Scutellarein 7-glucuronide	MeSH
Scutellarein-7-O-beta-glucuronide	MeSH
Scutellarein-7-O-glucuronide	MeSH
Flavone, 4',5,6,7-tetrahydroxy-, 7-beta-D-glucopyranuronoside	MeSH
Scutellarin b	MeSH

Chemical Formula

C₂₁H₁₈O₁₂

Average Mass

462.3630 Da

Monoisotopic Mass

462.07983 Da

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

scutellarin

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](OC2=C(O)C(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

InChI Key

DJSISFGPUUYILV-ZFORQUDYSA-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
Ageratum conyzoides	LOTUS Database	35616633
Clerodendrum indicum	LOTUS Database	35616633
Erigeron breviscapus	LOTUS Database	35616633
Galeopsis bifida	LOTUS Database	35616633
Monarda punctata	LOTUS Database	35616633
Oroxylum indicum	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Portulaca oleracea	LOTUS Database	35616633
Scoparia dulcis	LOTUS Database	35616633
Scutellaria alpina	LOTUS Database	35616633
Scutellaria barbata	LOTUS Database	35616633
Scutellaria indica	LOTUS Database	35616633
Scutellaria lateriflora	LOTUS Database	35616633
Sempervivum ruthenicum	LOTUS Database	35616633
Tripora divaricata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Beta-hydroxy acid
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Hydroxy acid
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:61278 )
glucosiduronic acid (CHEBI:61278 )
glycosyloxyflavone (CHEBI:61278 )
trihydroxyflavone (CHEBI:61278 )

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	0.46	ChemAxon
pKa (Strongest Acidic)	2.62	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.91 m³·mol⁻¹	ChemAxon
Polarizability	43.1 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

C00004221

Chemspider ID

161366

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Scutellarin

METLIN ID

Not Available

PubChem Compound

185617

PDB ID

Not Available

ChEBI ID

61278

Good Scents ID

Not Available

References

General References

Zhang Y, Zhang Z, Wang J, Zhang X, Zhao J, Bai N, Vijayalakshmi A, Huo Q: Scutellarin alleviates cerebral ischemia/reperfusion by suppressing oxidative stress and inflammatory responses via MAPK/NF-kappaB pathways in rats. Environ Toxicol. 2022 Dec;37(12):2889-2896. doi: 10.1002/tox.23645. Epub 2022 Aug 29. [PubMed:36036213 ]
Wang Z, Zhang P, Zhao Y, Yu F, Wang S, Liu K, Cheng X, Shi J, He Q, Xia Y, Cheng L: Scutellarin Protects Against Mitochondrial Reactive Oxygen Species-Dependent NLRP3 Inflammasome Activation to Attenuate Intervertebral Disc Degeneration. Front Bioeng Biotechnol. 2022 Aug 11;10:883118. doi: 10.3389/fbioe.2022.883118. eCollection 2022. [PubMed:36032701 ]
Huang H, Cao C, Miao Z, Yang X, Lai Y: Scutellarin Mediates Cytochrome P450 3A4 and 2C19 Expression via Pregnane X Receptor and Constitutive Androstane Receptor. Curr Mol Pharmacol. 2023;16(6):640-653. doi: 10.2174/1874467215666220823123852. [PubMed:36017831 ]
Teng M, Yuan X, Wang D, Gao H, Zhang K, Wang W, Zhao B: Scutellarin Loaded on Ultradeformable Nanoliposome Scutellarin EDTMP (S-UNL-E) Promotes Osteogenesis in Osteoporotic Rats. Stem Cells Int. 2022 Aug 16;2022:1395299. doi: 10.1155/2022/1395299. eCollection 2022. [PubMed:36017130 ]
Zhang S, Wei D, Lv S, Wang L, An H, Shao W, Wang Y, Huang Y, Peng D, Zhang Z: Scutellarin Modulates the Microbiota-Gut-Brain Axis and Improves Cognitive Impairment in APP/PS1 Mice. J Alzheimers Dis. 2022;89(3):955-975. doi: 10.3233/JAD-220532. [PubMed:35964195 ]
Costine B, Zhang M, Chhajed S, Pearson B, Chen S, Nadakuduti SS: Exploring native Scutellaria species provides insight into differential accumulation of flavones with medicinal properties. Sci Rep. 2022 Aug 1;12(1):13201. doi: 10.1038/s41598-022-17586-1. [PubMed:35915209 ]
Zhang CW, Guo JQ, Li WP, Luo YJ, Yao Y, Xu CQ, Shen GA, Suo FM, Guo BL: [Content correlation of eight phenolic acids and flavonoids in different medicinal parts of PA-type Perilla germplasms]. Zhongguo Zhong Yao Za Zhi. 2022 Jul;47(13):3447-3451. doi: 10.19540/j.cnki.cjcmm.20220316.104. [PubMed:35850795 ]
Mi XJ, Kim JK, Lee S, Moon SK, Kim YJ, Kim H: In vitro assessment of the anti-inflammatory and skin-moisturizing effects of Filipendula palmata (Pall.) Maxim. On human keratinocytes and identification of its bioactive phytochemicals. J Ethnopharmacol. 2022 Oct 5;296:115523. doi: 10.1016/j.jep.2022.115523. Epub 2022 Jul 7. [PubMed:35809756 ]
LOTUS database [Link]

Showing NP-Card for scutellarin (NP0224779)

MOL for NP0224779 (scutellarin)

3D MOL for NP0224779 (scutellarin)

3D SDF for NP0224779 (scutellarin)

3D-SDF for NP0224779 (scutellarin)

PDB for NP0224779 (scutellarin)

3D PDB for NP0224779 (scutellarin)

SMILES for NP0224779 (scutellarin)

INCHI for NP0224779 (scutellarin)

Structure for NP0224779 (scutellarin)

3D Structure for NP0224779 (scutellarin)