Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:30:27 UTC

Update Date

2022-03-07 02:55:41 UTC

HMDB ID

HMDB0038225

Secondary Accession Numbers

HMDB38225

Metabolite Identification

Common Name

Glycycoumarin

Description

Glycycoumarin belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Thus, glycycoumarin is considered to be a flavonoid. Glycycoumarin has been detected, but not quantified in, root vegetables. This could make glycycoumarin a potential biomarker for the consumption of these foods. Glycycoumarin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Glycycoumarin.

Structure

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


  Mrv0541 05061310182D          

 27 29  0  0  0  0            999 V2000
    4.2868    3.3000    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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
   -2.1434    3.7125    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   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
    2.1434    2.0625    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
    1.4289    2.4750    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
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
   -1.4289    0.8250    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  4  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 17 13  2  0  0  0  0
 18 10  2  0  0  0  0
 18 14  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20 14  2  0  0  0  0
 20 16  1  0  0  0  0
 21 15  1  0  0  0  0
 22 12  1  0  0  0  0
 23 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25 21  2  0  0  0  0
 26  3  1  0  0  0  0
 26 20  1  0  0  0  0
 27 19  1  0  0  0  0
 27 21  1  0  0  0  0
M  END

HMDB0038225
     RDKit          3D
Glycycoumarin
 47 49  0  0  0  0  0  0  0  0999 V2000
   -0.6631   -2.2539    0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -0.9095    0.6649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398   -0.4865   -0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -0.5575   -1.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561   -1.0557   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1139    0.0557   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4620    0.1038    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2410   -1.0132    2.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    1.3168    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -0.1157   -2.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809   -0.1621   -3.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.3807   -3.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2659    0.4435   -2.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166    0.9147   -2.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4956    0.9744   -2.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    1.4376   -2.7174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4893    0.5559   -0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    0.6011   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8821    0.0131   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577   -0.0071    0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.5600    1.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3162    0.5405    2.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9851    1.1450    1.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912    1.1638    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6886    1.7730    1.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    0.0743   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724    0.0088   -1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -2.7353   -0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -2.3053    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5124   -2.8814    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -1.8653   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1010   -1.5345   -1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.9725   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2061   -1.6016    2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0772   -0.6111    3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995   -1.6640    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4140    2.0324    2.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8826    1.0015    2.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6345    1.8943    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496   -0.4979   -3.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8123    0.7099   -4.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201   -0.4293   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9564   -0.4694   -0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0050    1.2818    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0573    1.5861    2.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    1.8865    1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524   -0.2715    0.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 17 26  2  0
 26 27  1  0
 27  3  1  0
 27 13  2  0
 24 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
 26 47  1  0
M  END


  Mrv0541 05061310182D          

 27 29  0  0  0  0            999 V2000
    4.2868    3.3000    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
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
   -2.1434    3.7125    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   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
    2.1434    2.0625    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
    1.4289    2.4750    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
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
   -1.4289    0.8250    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  4  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 17 13  2  0  0  0  0
 18 10  2  0  0  0  0
 18 14  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20 14  2  0  0  0  0
 20 16  1  0  0  0  0
 21 15  1  0  0  0  0
 22 12  1  0  0  0  0
 23 17  1  0  0  0  0
 24 18  1  0  0  0  0
 25 21  2  0  0  0  0
 26  3  1  0  0  0  0
 26 20  1  0  0  0  0
 27 19  1  0  0  0  0
 27 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038225

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3

> <INCHI_KEY>
NZYSZZDSYIBYLC-UHFFFAOYSA-N

> <FORMULA>
C21H20O6

> <MOLECULAR_WEIGHT>
368.3799

> <EXACT_MASS>
368.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.007957752170114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.111647179333334

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.554700103996533

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.601662780880913

> <JCHEM_PKA_STRONGEST_BASIC>
-4.873010248114108

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
102.64939999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glycycoumarin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038225
     RDKit          3D
Glycycoumarin
 47 49  0  0  0  0  0  0  0  0999 V2000
   -0.6631   -2.2539    0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -0.9095    0.6649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398   -0.4865   -0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -0.5575   -1.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561   -1.0557   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1139    0.0557   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4620    0.1038    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2410   -1.0132    2.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    1.3168    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -0.1157   -2.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809   -0.1621   -3.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.3807   -3.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2659    0.4435   -2.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166    0.9147   -2.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4956    0.9744   -2.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    1.4376   -2.7174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4893    0.5559   -0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    0.6011   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8821    0.0131   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577   -0.0071    0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.5600    1.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3162    0.5405    2.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9851    1.1450    1.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912    1.1638    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6886    1.7730    1.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    0.0743   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724    0.0088   -1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -2.7353   -0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -2.3053    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5124   -2.8814    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -1.8653   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1010   -1.5345   -1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.9725   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2061   -1.6016    2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0772   -0.6111    3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995   -1.6640    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4140    2.0324    2.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8826    1.0015    2.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6345    1.8943    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496   -0.4979   -3.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8123    0.7099   -4.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201   -0.4293   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9564   -0.4694   -0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0050    1.2818    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0573    1.5861    2.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    1.8865    1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524   -0.2715    0.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 17 26  2  0
 26 27  1  0
 27  3  1  0
 27 13  2  0
 24 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
 26 47  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   26                                                            
CONECT    4    6   11                                                       
CONECT    5    7   12                                                       
CONECT    6    4   14                                                       
CONECT    7    5   13                                                       
CONECT    8   12   17                                                       
CONECT    9   15   16                                                       
CONECT   10   18   19                                                       
CONECT   11    1    2    4                                                  
CONECT   12    5    8   22                                                  
CONECT   13    7   15   17                                                  
CONECT   14    6   18   20                                                  
CONECT   15    9   13   21                                                  
CONECT   16    9   19   20                                                  
CONECT   17    8   13   23                                                  
CONECT   18   10   14   24                                                  
CONECT   19   10   16   27                                                  
CONECT   20   14   16   26                                                  
CONECT   21   15   25   27                                                  
CONECT   22   12                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   21                                                            
CONECT   26    3   20                                                       
CONECT   27   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0038225
HETATM    1  C1  UNL     1      -0.663  -2.254   0.908  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.044  -0.909   0.665  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.040  -0.487  -0.650  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.174  -0.558  -1.424  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.456  -1.056  -0.834  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.114   0.056  -0.096  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.462   0.104   1.150  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.241  -1.013   2.080  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.122   1.317   1.693  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.071  -0.116  -2.734  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.181  -0.162  -3.559  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.856   0.381  -3.237  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.266   0.443  -2.446  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.417   0.915  -2.933  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.496   0.974  -2.180  1.00  0.00           C  
HETATM   16  O4  UNL     1       3.556   1.438  -2.717  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.489   0.556  -0.862  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.707   0.601  -0.071  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.882   0.013  -0.561  1.00  0.00           C  
HETATM   20  C16 UNL     1       6.058  -0.007   0.156  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.134   0.560   1.411  1.00  0.00           C  
HETATM   22  O5  UNL     1       7.316   0.540   2.136  1.00  0.00           O  
HETATM   23  C18 UNL     1       4.985   1.145   1.909  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.791   1.164   1.176  1.00  0.00           C  
HETATM   25  O6  UNL     1       2.689   1.773   1.743  1.00  0.00           O  
HETATM   26  C20 UNL     1       1.315   0.074  -0.361  1.00  0.00           C  
HETATM   27  C21 UNL     1       0.172   0.009  -1.150  1.00  0.00           C  
HETATM   28  H1  UNL     1      -0.222  -2.735  -0.013  1.00  0.00           H  
HETATM   29  H2  UNL     1       0.153  -2.305   1.664  1.00  0.00           H  
HETATM   30  H3  UNL     1      -1.512  -2.881   1.188  1.00  0.00           H  
HETATM   31  H4  UNL     1      -3.231  -1.865  -0.099  1.00  0.00           H  
HETATM   32  H5  UNL     1      -4.101  -1.535  -1.583  1.00  0.00           H  
HETATM   33  H6  UNL     1      -4.336   0.973  -0.701  1.00  0.00           H  
HETATM   34  H7  UNL     1      -5.206  -1.602   2.136  1.00  0.00           H  
HETATM   35  H8  UNL     1      -4.077  -0.611   3.130  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.399  -1.664   1.877  1.00  0.00           H  
HETATM   37  H10 UNL     1      -4.414   2.032   2.161  1.00  0.00           H  
HETATM   38  H11 UNL     1      -5.883   1.002   2.450  1.00  0.00           H  
HETATM   39  H12 UNL     1      -5.634   1.894   0.879  1.00  0.00           H  
HETATM   40  H13 UNL     1      -4.050  -0.498  -3.222  1.00  0.00           H  
HETATM   41  H14 UNL     1      -0.812   0.710  -4.247  1.00  0.00           H  
HETATM   42  H15 UNL     1       4.820  -0.429  -1.539  1.00  0.00           H  
HETATM   43  H16 UNL     1       6.956  -0.469  -0.247  1.00  0.00           H  
HETATM   44  H17 UNL     1       8.005   1.282   2.067  1.00  0.00           H  
HETATM   45  H18 UNL     1       5.057   1.586   2.891  1.00  0.00           H  
HETATM   46  H19 UNL     1       1.786   1.887   1.354  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.252  -0.272   0.643  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4   27
CONECT    4    5   10
CONECT    5    6   31   32
CONECT    6    7    7   33
CONECT    7    8    9
CONECT    8   34   35   36
CONECT    9   37   38   39
CONECT   10   11   12   12
CONECT   11   40
CONECT   12   13   41
CONECT   13   14   27   27
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   18   26   26
CONECT   18   19   19   24
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   21   22   23
CONECT   22   44
CONECT   23   24   24   45
CONECT   24   25
CONECT   25   46
CONECT   26   27   47
END

HMDB0038225
     RDKit          3D
Glycycoumarin
 47 49  0  0  0  0  0  0  0  0999 V2000
   -0.6631   -2.2539    0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -0.9095    0.6649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398   -0.4865   -0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -0.5575   -1.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561   -1.0557   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1139    0.0557   -0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4620    0.1038    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2410   -1.0132    2.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    1.3168    1.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -0.1157   -2.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809   -0.1621   -3.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8564    0.3807   -3.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2659    0.4435   -2.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166    0.9147   -2.9331 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4956    0.9744   -2.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5563    1.4376   -2.7174 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4893    0.5559   -0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    0.6011   -0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8821    0.0131   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577   -0.0071    0.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344    0.5600    1.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3162    0.5405    2.1360 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9851    1.1450    1.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912    1.1638    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6886    1.7730    1.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151    0.0743   -0.3606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724    0.0088   -1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -2.7353   -0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -2.3053    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5124   -2.8814    1.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2308   -1.8653   -0.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1010   -1.5345   -1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3365    0.9725   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2061   -1.6016    2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0772   -0.6111    3.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3995   -1.6640    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4140    2.0324    2.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8826    1.0015    2.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6345    1.8943    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496   -0.4979   -3.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8123    0.7099   -4.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8201   -0.4293   -1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9564   -0.4694   -0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0050    1.2818    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0573    1.5861    2.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7863    1.8865    1.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524   -0.2715    0.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 17 26  2  0
 26 27  1  0
 27  3  1  0
 27 13  2  0
 24 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 19 42  1  0
 20 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
 26 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2,4-Dihydroxy-phenyl)-7-hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-2-one	ChEBI
3-(2,4-Dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ci	HMDB

Chemical Formula

C₂₁H₂₀O₆

Average Molecular Weight

368.3799

Monoisotopic Molecular Weight

368.125988372

IUPAC Name

3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Traditional Name

glycycoumarin

CAS Registry Number

94805-82-0

SMILES

COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C21H20O6/c1-11(2)4-6-14-18(24)10-19-16(20(14)26-3)9-15(21(25)27-19)13-7-5-12(22)8-17(13)23/h4-5,7-10,22-24H,6H2,1-3H3

InChI Key

NZYSZZDSYIBYLC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Hydroxyisoflavonoids

Direct Parent

Hydroxyisoflavonoids

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflav-3-enone skeleton
7-hydroxycoumarin
Hydroxycoumarin
Coumarin
Benzopyran
1-benzopyran
Anisole
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:69087 )
resorcinols (CHEBI:69087 )
coumarins (CHEBI:69087 )
Other Flavonoids (LMPK12160018 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038225)
Cell membrane (HMDB: HMDB0038225)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038225)

Source

Exogenous

Exogenous (HMDB: HMDB0038225)

Food

Food (HMDB: HMDB0038225)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB0038225)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038225)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	243.5 - 244.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.11 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.06	ALOGPS
logP	4.11	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.6	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.65 m³·mol⁻¹	ChemAxon
Polarizability	39.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DarkChem	[M+H]+	187.822	31661259
DarkChem	[M-H]-	189.536	31661259
DeepCCS	[M+H]+	190.957	30932474
DeepCCS	[M-H]-	188.599	30932474
DeepCCS	[M-2H]-	222.22	30932474
DeepCCS	[M+Na]+	197.449	30932474
AllCCS	[M+H]+	188.5	32859911
AllCCS	[M+H-H2O]+	185.4	32859911
AllCCS	[M+NH4]+	191.4	32859911
AllCCS	[M+Na]+	192.2	32859911
AllCCS	[M-H]-	187.4	32859911
AllCCS	[M+Na-2H]-	187.0	32859911
AllCCS	[M+HCOO]-	186.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.51 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8442 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2264.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	240.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	655.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	442.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1004.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	480.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1346.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	249.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	327.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glycycoumarin	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1	4761.9	Standard polar	33892256
Glycycoumarin	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1	3086.6	Standard non polar	33892256
Glycycoumarin	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C(=O)O2)C1=C(O)C=C(O)C=C1	3551.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glycycoumarin,1TMS,isomer #1	COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O2	3294.6	Semi standard non polar	33892256
Glycycoumarin,1TMS,isomer #2	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O2	3250.8	Semi standard non polar	33892256
Glycycoumarin,1TMS,isomer #3	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O2	3264.5	Semi standard non polar	33892256
Glycycoumarin,2TMS,isomer #1	COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O)C(=O)O2	3170.4	Semi standard non polar	33892256
Glycycoumarin,2TMS,isomer #2	COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C)C(=O)O2	3170.0	Semi standard non polar	33892256
Glycycoumarin,2TMS,isomer #3	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O2	3166.7	Semi standard non polar	33892256
Glycycoumarin,3TMS,isomer #1	COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C)C(=O)O2	3154.5	Semi standard non polar	33892256
Glycycoumarin,1TBDMS,isomer #1	COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O)C(=O)O2	3561.7	Semi standard non polar	33892256
Glycycoumarin,1TBDMS,isomer #2	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2	3513.3	Semi standard non polar	33892256
Glycycoumarin,1TBDMS,isomer #3	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O2	3531.5	Semi standard non polar	33892256
Glycycoumarin,2TBDMS,isomer #1	COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O)C(=O)O2	3662.5	Semi standard non polar	33892256
Glycycoumarin,2TBDMS,isomer #2	COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2	3629.1	Semi standard non polar	33892256
Glycycoumarin,2TBDMS,isomer #3	COC1=C(CC=C(C)C)C(O)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2	3638.1	Semi standard non polar	33892256
Glycycoumarin,3TBDMS,isomer #1	COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2	3781.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Glycycoumarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fe3-1019000000-282ddd8e8c26f5157190	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycycoumarin GC-MS (3 TMS) - 70eV, Positive	splash10-00vi-1000090000-c783ed22b161225cef62	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycycoumarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glycycoumarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycycoumarin 6V, Positive-QTOF	splash10-014i-0239000000-d9d32e4f7d08239440a1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Glycycoumarin 6V, Negative-QTOF	splash10-014i-0139000000-a756c8040aba88b4cf47	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 10V, Positive-QTOF	splash10-014i-0019000000-e8f5e2687e5267423792	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 20V, Positive-QTOF	splash10-02t9-2019000000-d045204802bd0020e448	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 40V, Positive-QTOF	splash10-014i-7192000000-e9862c4ef6e27eeb4017	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 10V, Negative-QTOF	splash10-014i-0009000000-20b68087ed6e95096b14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 20V, Negative-QTOF	splash10-066r-0329000000-c3865e9020277be80782	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 40V, Negative-QTOF	splash10-0a4i-4921000000-1394f8833dcd0fe74eec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 10V, Negative-QTOF	splash10-014i-0009000000-53fb202c32e20191eab9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 20V, Negative-QTOF	splash10-014r-0019000000-0adc5122ed4fb3bdacc4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 40V, Negative-QTOF	splash10-01bi-0029000000-174c1e96872b10850e45	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 10V, Positive-QTOF	splash10-02t9-0009000000-ae0ab568c3686266872c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 20V, Positive-QTOF	splash10-03di-0019000000-726729680437cd2b03a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glycycoumarin 40V, Positive-QTOF	splash10-015a-0093000000-7fbdb116445186172827	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB017468

KNApSAcK ID

C00010040

Chemspider ID

4476511

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317756

PDB ID

Not Available

ChEBI ID

69087

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1866371

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tanaka Y, Kikuzaki H, Fukuda S, Nakatani N: Antibacterial compounds of licorice against upper airway respiratory tract pathogens. J Nutr Sci Vitaminol (Tokyo). 2001 Jun;47(3):270-3. [PubMed:11575586 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Glycycoumarin (HMDB0038225)

MOL for HMDB0038225 (Glycycoumarin)

3D MOL for HMDB0038225 (Glycycoumarin)

3D SDF for HMDB0038225 (Glycycoumarin)

3D-SDF for HMDB0038225 (Glycycoumarin)

PDB for HMDB0038225 (Glycycoumarin)

3D PDB for HMDB0038225 (Glycycoumarin)

SMILES for HMDB0038225 (Glycycoumarin)

INCHI for HMDB0038225 (Glycycoumarin)

Structure for HMDB0038225 (Glycycoumarin)

3D Structure for HMDB0038225 (Glycycoumarin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra