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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 04:09:49 UTC

Update Date

2021-09-23 04:09:49 UTC

HMDB ID

HMDB0301981

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside

Description

Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside, also known as homoorientin or luteolin-6-C-beta-D-glucoside, is a member of the class of compounds known as flavonoid c-glycosides. Flavonoid c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside can be synthesized from luteolin. Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside is also a parent compound for other transformation products, including but not limited to, isoorientin 7-O-glucoside, 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucosyl]isoorientin, and 7-O-(6-sinapoylglucosyl)isoorientin. Isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside can be found in barley, which makes isoorientin 7-o-(6'''-o-(e)-feruloyl)glucoside a potential biomarker for the consumption of this food product.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652307301920022D          

 37 40  0  0  1  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    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
    0.0000    2.4750    0.0000 C   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
   -0.7145    1.2375    0.0000 C   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
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  2  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
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  4  2  0  0  0  0
 12  7  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 16  1  0  0  0  0
 20 21  1  0  0  0  0
 22  6  1  0  0  0  0
 23  8  1  0  0  0  0
 24  9  1  0  0  0  0
 25 10  2  0  0  0  0
 26 11  1  0  0  0  0
 17 27  1  0  0  0  0
 28 18  1  0  0  0  0
 19 29  1  0  0  0  0
 20 30  1  0  0  0  0
 31 12  1  0  0  0  0
 31 13  1  0  0  0  0
 14 32  1  0  0  0  0
 21 32  1  0  0  0  0
 14 33  1  6  0  0  0
 17 34  1  1  0  0  0
 19 35  1  6  0  0  0
 20 36  1  1  0  0  0
 21 37  1  6  0  0  0
M  END

HMDB0301981
     RDKit          3D
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside
 52 55  0  0  0  0  0  0  0  0999 V2000
    0.4601    1.9199    1.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1294    1.1493    1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976    1.2258    1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    0.4448    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7517    0.5264    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.5609    1.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7256    1.5645    1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4805    0.4533    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417    0.4589    1.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8770   -0.5841    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6258   -1.6889   -0.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4869   -0.5830    0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -0.4349   -0.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -0.5231   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -1.4618   -1.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060   -1.5907   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1007   -2.4923   -2.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421   -0.8152   -0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8091   -0.9306   -0.8141 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1791    0.3532   -1.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4222    0.7680   -1.3226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3641    2.3396   -1.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6845    2.8268   -2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2478    0.4260   -0.1157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5979    0.4766   -0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9644   -0.9471    0.4365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5676   -1.0616    1.6848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4653   -1.1616    0.5438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3332   -2.5586    0.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160    0.1173    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    0.8941    0.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5589    0.2594    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253    1.9506    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8178    2.4713    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2738    2.3797    1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4391   -0.3049    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845   -2.5049   -0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406   -1.4265   -0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5247   -2.0622   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -3.1605   -2.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0770   -1.6853   -1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9758    0.5429   -2.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478    2.5799   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3969    2.7204   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415    2.0592   -2.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0977    1.2031    0.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377   -0.4563   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4740   -1.6854   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2217   -1.9240    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1045   -0.5338    1.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -2.6456    1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.5513    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 18 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 12  5  1  0
 32 14  1  0
 28 19  1  0
  3 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  6
 21 42  1  6
 22 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  1
 25 47  1  0
 26 48  1  6
 27 49  1  0
 28 50  1  1
 29 51  1  0
 31 52  1  0
M  END


  Mrv1652307301920022D          

 37 40  0  0  1  0            999 V2000
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    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
    0.0000    2.4750    0.0000 C   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
   -0.7145    1.2375    0.0000 C   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
    4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  2  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
    3.5724    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  4  2  0  0  0  0
 12  7  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 18 16  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 16  1  0  0  0  0
 20 21  1  0  0  0  0
 22  6  1  0  0  0  0
 23  8  1  0  0  0  0
 24  9  1  0  0  0  0
 25 10  2  0  0  0  0
 26 11  1  0  0  0  0
 17 27  1  0  0  0  0
 28 18  1  0  0  0  0
 19 29  1  0  0  0  0
 20 30  1  0  0  0  0
 31 12  1  0  0  0  0
 31 13  1  0  0  0  0
 14 32  1  0  0  0  0
 21 32  1  0  0  0  0
 14 33  1  6  0  0  0
 17 34  1  1  0  0  0
 19 35  1  6  0  0  0
 20 36  1  1  0  0  0
 21 37  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0301981

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(CO)O[C@@]([H])(C2=C(O)C3=C(OC(=CC3=O)C3=CC(O)=C(O)C=C3)C=C2O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

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

> <INCHI_KEY>
ODBRNZZJSYPIDI-VJXVFPJBSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.3769

> <EXACT_MASS>
448.100561482

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.53620144338001

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
-0.35419709299999974

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.710374345458051

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.13760442806852

> <JCHEM_PKA_STRONGEST_BASIC>
-2.979192626943843

> <JCHEM_POLAR_SURFACE_AREA>
197.36999999999998

> <JCHEM_REFRACTIVITY>
108.01309999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
isoorientin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301981
     RDKit          3D
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside
 52 55  0  0  0  0  0  0  0  0999 V2000
    0.4601    1.9199    1.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1294    1.1493    1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976    1.2258    1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    0.4448    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7517    0.5264    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.5609    1.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7256    1.5645    1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4805    0.4533    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417    0.4589    1.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8770   -0.5841    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6258   -1.6889   -0.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4869   -0.5830    0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -0.4349   -0.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -0.5231   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -1.4618   -1.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060   -1.5907   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1007   -2.4923   -2.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421   -0.8152   -0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8091   -0.9306   -0.8141 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1791    0.3532   -1.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4222    0.7680   -1.3226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3641    2.3396   -1.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6845    2.8268   -2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2478    0.4260   -0.1157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5979    0.4766   -0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9644   -0.9471    0.4365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5676   -1.0616    1.6848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4653   -1.1616    0.5438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3332   -2.5586    0.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160    0.1173    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    0.8941    0.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5589    0.2594    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253    1.9506    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8178    2.4713    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2738    2.3797    1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4391   -0.3049    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845   -2.5049   -0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406   -1.4265   -0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5247   -2.0622   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -3.1605   -2.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0770   -1.6853   -1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9758    0.5429   -2.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478    2.5799   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3969    2.7204   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415    2.0592   -2.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0977    1.2031    0.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377   -0.4563   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4740   -1.6854   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2217   -1.9240    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1045   -0.5338    1.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -2.6456    1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.5513    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 18 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 12  5  1  0
 32 14  1  0
 28 19  1  0
  3 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  6
 21 42  1  6
 22 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  1
 25 47  1  0
 26 48  1  6
 27 49  1  0
 28 50  1  1
 29 51  1  0
 31 52  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   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  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       9.336   5.390   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       8.002   7.700   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.668   5.390   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.335   7.700   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.001   5.390   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    7    9                                                       
CONECT    4   10   12                                                       
CONECT    5   11   13                                                       
CONECT    6   14   22                                                       
CONECT    7    1    3   12                                                  
CONECT    8    2    9   23                                                  
CONECT    9    3    8   24                                                  
CONECT   10    4   15   25                                                  
CONECT   11    5   16   26                                                  
CONECT   12    4    7   31                                                  
CONECT   13    5   15   31                                                  
CONECT   14    6   17   32   33                                             
CONECT   15   10   13   18                                                  
CONECT   16   11   18   21                                                  
CONECT   17   14   19   27   34                                             
CONECT   18   15   16   28                                                  
CONECT   19   17   20   29   35                                             
CONECT   20   19   21   30   36                                             
CONECT   21   16   20   32   37                                             
CONECT   22    6                                                            
CONECT   23    8                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   20                                                            
CONECT   31   12   13                                                       
CONECT   32   14   21                                                       
CONECT   33   14                                                            
CONECT   34   17                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    HMDB0301981
HETATM    1  O1  UNL     1       0.460   1.920   1.963  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.129   1.149   1.209  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.498   1.226   1.276  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.306   0.445   0.517  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.752   0.526   0.614  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.383   1.561   1.213  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.726   1.565   1.421  1.00  0.00           C  
HETATM    8  C7  UNL     1       7.481   0.453   1.003  1.00  0.00           C  
HETATM    9  O2  UNL     1       8.842   0.459   1.229  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.877  -0.584   0.401  1.00  0.00           C  
HETATM   11  O3  UNL     1       7.626  -1.689  -0.012  1.00  0.00           O  
HETATM   12  C9  UNL     1       5.487  -0.583   0.181  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.708  -0.435  -0.337  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.404  -0.523  -0.412  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.854  -1.462  -1.308  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.506  -1.591  -1.407  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.101  -2.492  -2.256  1.00  0.00           O  
HETATM   18  C13 UNL     1      -1.342  -0.815  -0.642  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.809  -0.931  -0.814  1.00  0.00           C  
HETATM   20  O6  UNL     1      -3.179   0.353  -1.263  1.00  0.00           O  
HETATM   21  C15 UNL     1      -4.422   0.768  -1.323  1.00  0.00           C  
HETATM   22  C16 UNL     1      -4.364   2.340  -1.298  1.00  0.00           C  
HETATM   23  O7  UNL     1      -3.685   2.827  -2.368  1.00  0.00           O  
HETATM   24  C17 UNL     1      -5.248   0.426  -0.116  1.00  0.00           C  
HETATM   25  O8  UNL     1      -6.598   0.477  -0.485  1.00  0.00           O  
HETATM   26  C18 UNL     1      -4.964  -0.947   0.437  1.00  0.00           C  
HETATM   27  O9  UNL     1      -5.568  -1.062   1.685  1.00  0.00           O  
HETATM   28  C19 UNL     1      -3.465  -1.162   0.544  1.00  0.00           C  
HETATM   29  O10 UNL     1      -3.333  -2.559   0.792  1.00  0.00           O  
HETATM   30  C20 UNL     1      -0.816   0.117   0.243  1.00  0.00           C  
HETATM   31  O11 UNL     1      -1.644   0.894   0.993  1.00  0.00           O  
HETATM   32  C21 UNL     1       0.559   0.259   0.354  1.00  0.00           C  
HETATM   33  H1  UNL     1       2.925   1.951   2.018  1.00  0.00           H  
HETATM   34  H2  UNL     1       4.818   2.471   1.531  1.00  0.00           H  
HETATM   35  H3  UNL     1       7.274   2.380   1.867  1.00  0.00           H  
HETATM   36  H4  UNL     1       9.439  -0.305   0.899  1.00  0.00           H  
HETATM   37  H5  UNL     1       7.284  -2.505  -0.460  1.00  0.00           H  
HETATM   38  H6  UNL     1       5.041  -1.426  -0.297  1.00  0.00           H  
HETATM   39  H7  UNL     1       1.525  -2.062  -1.913  1.00  0.00           H  
HETATM   40  H8  UNL     1      -0.589  -3.160  -2.824  1.00  0.00           H  
HETATM   41  H9  UNL     1      -3.077  -1.685  -1.524  1.00  0.00           H  
HETATM   42  H10 UNL     1      -4.976   0.543  -2.275  1.00  0.00           H  
HETATM   43  H11 UNL     1      -3.848   2.580  -0.344  1.00  0.00           H  
HETATM   44  H12 UNL     1      -5.397   2.720  -1.214  1.00  0.00           H  
HETATM   45  H13 UNL     1      -3.241   2.059  -2.855  1.00  0.00           H  
HETATM   46  H14 UNL     1      -5.098   1.203   0.679  1.00  0.00           H  
HETATM   47  H15 UNL     1      -6.938  -0.456  -0.533  1.00  0.00           H  
HETATM   48  H16 UNL     1      -5.474  -1.685  -0.207  1.00  0.00           H  
HETATM   49  H17 UNL     1      -5.222  -1.924   2.068  1.00  0.00           H  
HETATM   50  H18 UNL     1      -3.105  -0.534   1.329  1.00  0.00           H  
HETATM   51  H19 UNL     1      -2.853  -2.646   1.650  1.00  0.00           H  
HETATM   52  H20 UNL     1      -1.537   1.551   1.703  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   32
CONECT    3    4    4   33
CONECT    4    5   13
CONECT    5    6    6   12
CONECT    6    7   34
CONECT    7    8    8   35
CONECT    8    9   10
CONECT    9   36
CONECT   10   11   12   12
CONECT   11   37
CONECT   12   38
CONECT   13   14
CONECT   14   15   15   32
CONECT   15   16   39
CONECT   16   17   18   18
CONECT   17   40
CONECT   18   19   30
CONECT   19   20   28   41
CONECT   20   21
CONECT   21   22   24   42
CONECT   22   23   43   44
CONECT   23   45
CONECT   24   25   26   46
CONECT   25   47
CONECT   26   27   28   48
CONECT   27   49
CONECT   28   29   50
CONECT   29   51
CONECT   30   31   32   32
CONECT   31   52
END

HMDB0301981
     RDKit          3D
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside
 52 55  0  0  0  0  0  0  0  0999 V2000
    0.4601    1.9199    1.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1294    1.1493    1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976    1.2258    1.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    0.4448    0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7517    0.5264    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.5609    1.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7256    1.5645    1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4805    0.4533    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8417    0.4589    1.2293 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8770   -0.5841    0.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6258   -1.6889   -0.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4869   -0.5830    0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7083   -0.4349   -0.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -0.5231   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541   -1.4618   -1.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5060   -1.5907   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1007   -2.4923   -2.2556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421   -0.8152   -0.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8091   -0.9306   -0.8141 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1791    0.3532   -1.2633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4222    0.7680   -1.3226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3641    2.3396   -1.2975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6845    2.8268   -2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2478    0.4260   -0.1157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5979    0.4766   -0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9644   -0.9471    0.4365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5676   -1.0616    1.6848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4653   -1.1616    0.5438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3332   -2.5586    0.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8160    0.1173    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6437    0.8941    0.9933 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5589    0.2594    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253    1.9506    2.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8178    2.4713    1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2738    2.3797    1.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4391   -0.3049    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845   -2.5049   -0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406   -1.4265   -0.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5247   -2.0622   -1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886   -3.1605   -2.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0770   -1.6853   -1.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9758    0.5429   -2.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478    2.5799   -0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3969    2.7204   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2415    2.0592   -2.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0977    1.2031    0.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9377   -0.4563   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4740   -1.6854   -0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2217   -1.9240    2.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1045   -0.5338    1.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -2.6456    1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367    1.5513    1.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 18 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 12  5  1  0
 32 14  1  0
 28 19  1  0
  3 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  6
 21 42  1  6
 22 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  1
 25 47  1  0
 26 48  1  6
 27 49  1  0
 28 50  1  1
 29 51  1  0
 31 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-6-beta-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
Homoorientin	ChEBI
Luteolin-6-C-beta-D-glucoside	ChEBI
2-(3,4-Dihydroxyphenyl)-6-b-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one	Generator
2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one	Generator
Luteolin-6-C-b-D-glucoside	Generator
Luteolin-6-C-β-D-glucoside	Generator
6-GLC-Luteolin	MeSH
Iso-orientin	MeSH
Luteolin-6-C-glucoside	MeSH

Chemical Formula

C₂₁H₂₀O₁₁

Average Molecular Weight

448.3769

Monoisotopic Molecular Weight

448.100561482

IUPAC Name

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

Traditional Name

isoorientin

CAS Registry Number

Not Available

SMILES

[H][C@]1(CO)O[C@@]([H])(C2=C(O)C3=C(OC(=CC3=O)C3=CC(O)=C(O)C=C3)C=C2O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O

InChI Identifier

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

InChI Key

ODBRNZZJSYPIDI-VJXVFPJBSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid C-glycosides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:17965 )
flavone C-glycoside (CHEBI:17965 )
flavones (C01821 )
Flavones and Flavonols (C01821 )

Ontology

Not Available

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.35	ChemAxon
pKa (Strongest Acidic)	6.14	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	42.54 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	205.928	32859911
AllCCS	[M+H-H2O]+	203.435	32859911
AllCCS	[M+Na]+	208.878	32859911
AllCCS	[M+NH4]+	208.222	32859911
AllCCS	[M-H]-	203.828	32859911
AllCCS	[M+Na-2H]-	204.559	32859911
AllCCS	[M+HCOO]-	205.524	32859911
DeepCCS	[M+H]+	197.009	30932474
DeepCCS	[M-H]-	194.657	30932474
DeepCCS	[M-2H]-	228.001	30932474
DeepCCS	[M+Na]+	202.921	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside,4TMS,isomer #46	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C(=O)C=C(C1=CC=C(O)C(O)=C1)O2	4010.7	Semi standard non polar	33892256
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside,4TMS,isomer #46	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C(=O)C=C(C1=CC=C(O)C(O)=C1)O2	4044.6	Standard non polar	33892256
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside,4TMS,isomer #46	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C(=O)C=C(C1=CC=C(O)C(O)=C1)O2	4889.0	Standard polar	33892256
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside,5TMS,isomer #36	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C(=O)C=C(C1=CC=C(O)C(O)=C1)O2	3966.5	Semi standard non polar	33892256
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside,5TMS,isomer #36	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C(=O)C=C(C1=CC=C(O)C(O)=C1)O2	4010.6	Standard non polar	33892256
Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside,5TMS,isomer #36	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C(=O)C=C(C1=CC=C(O)C(O)=C1)O2	4596.7	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside LC-ESI-QFT 31V, positive-QTOF	splash10-001i-0009600000-63aca9b4e94182b5fa78	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside LC-ESI-IT 31V, positive-QTOF	splash10-001i-0007900000-066f6c97856af91728a5	2020-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 10V, Positive-QTOF	splash10-000t-0000900000-4deb7298d7dc5928ad89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 20V, Positive-QTOF	splash10-01pk-3321900000-00aa5483c1d5c8e7a90b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 40V, Positive-QTOF	splash10-06r2-5397200000-4d4fad2cb7e71de05fec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 10V, Negative-QTOF	splash10-0002-0011900000-17de0eb864f93a041052	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 20V, Negative-QTOF	splash10-05ds-9336700000-89bd0f817e7ef84d44ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 40V, Negative-QTOF	splash10-052g-9442000000-e1cf40127250e554e9f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 10V, Positive-QTOF	splash10-0002-0000900000-6cdaf2bc31caca882f1d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 20V, Positive-QTOF	splash10-0002-0000900000-6cdaf2bc31caca882f1d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 40V, Positive-QTOF	splash10-014j-0309600000-60823208b2459e4934c5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 10V, Negative-QTOF	splash10-0002-0000900000-e34b057bc120eef7d6a0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 20V, Negative-QTOF	splash10-0002-0000900000-578e80e06a8f791630d8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside 40V, Negative-QTOF	splash10-01t9-0955400000-d57d92c5c589d52431dc	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoorientin

METLIN ID

Not Available

PubChem Compound

114776

PDB ID

Not Available

ChEBI ID

17965

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1700251

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside (HMDB0301981)

MOL for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

3D MOL for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

3D SDF for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

3D-SDF for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

PDB for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

3D PDB for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

SMILES for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

INCHI for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

Structure for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

3D Structure for HMDB0301981 (Isoorientin 7-O-(6'''-O-(E)-feruloyl)glucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra