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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:21:31 UTC

Update Date

2022-03-07 02:53:47 UTC

HMDB ID

HMDB0033611

Secondary Accession Numbers

HMDB33611

Metabolite Identification

Common Name

Licocoumarin A

Description

Licocoumarin A belongs to the class of organic compounds known as hydroxyisoflavonoids. These are organic compounds containing an isoflavonoid skeleton carrying one or more hydroxyl groups. Licocoumarin A has been detected, but not quantified in, several different foods, such as herbs and spices, herbal tea, green tea, black tea, and teas (Camellia sinensis). This could make licocoumarin a a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licocoumarin A.

Structure

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


  Mrv0541 05061307142D          

 30 32  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    5.0013    2.0625    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
    5.0013   -0.4125    0.0000 C   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
    5.7158    0.0000    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
    5.7158    3.3000    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
    2.1434   -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
    5.0013    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
    3.5724   -0.4125    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
    0.7145   -1.2375    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
    2.1434   -1.2375    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
    6.4302    1.2375    0.0000 O   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
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  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
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 13  2  0  0  0  0
 20 17  1  0  0  0  0
 21 12  1  0  0  0  0
 21 18  2  0  0  0  0
 22 11  1  0  0  0  0
 22 19  2  0  0  0  0
 23 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 16  2  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 25  2  0  0  0  0
 30 24  1  0  0  0  0
 30 25  1  0  0  0  0
M  END

HMDB0033611
     RDKit          3D
Licocoumarin A
 56 58  0  0  0  0  0  0  0  0999 V2000
    4.9414   -0.2608    1.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625    0.8276    1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7373    1.5316    2.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7596    1.2508   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    0.8216   -1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.2509   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4883   -1.5587   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8392   -1.7959   -1.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477   -2.6329   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -2.3846   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -1.1243   -0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3305   -0.8528   -0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    0.0461   -1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418    0.2856   -1.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3063    1.1619   -2.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586    1.3918   -2.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702    0.6761   -1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7202    0.9035   -1.4828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431   -0.1980   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4987   -0.9526    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -0.0358    1.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0479    0.1335    1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1564   -0.5942    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3240    1.0740    3.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615   -0.4050   -0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7883   -1.2640    0.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947   -1.4853   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0711   -2.3064    0.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6582   -0.0530   -1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942    1.1973   -1.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046   -0.1830    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698   -0.0702    2.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -1.2498    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1133    1.8114    3.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0744    2.4641    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5351    0.8219    2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4867    2.1001   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7630    0.5600   -2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    1.6977   -1.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454   -1.0797   -1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530   -3.6374   -0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294   -3.2269   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3072    0.5732   -2.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6946    1.6864   -3.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1729    2.0893   -3.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1558    1.5549   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982   -1.8192    0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4265   -1.2984   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9967    0.5286    1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4747   -0.2138    0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8892   -1.6746    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0576   -0.5044    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6929    0.7780    3.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3747    1.0024    3.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1281    2.1245    2.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6258    2.0187   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 19 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 11 29  2  0
 29 30  1  0
 29  6  1  0
 27 12  1  0
 25 14  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 30 56  1  0
M  END


  Mrv0541 05061307142D          

 30 32  0  0  0  0            999 V2000
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    5.0013    2.0625    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
    5.0013   -0.4125    0.0000 C   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
    5.7158    0.0000    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
    5.7158    3.3000    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
    2.1434   -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
    5.0013    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
    3.5724   -0.4125    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
    0.7145   -1.2375    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
    2.1434   -1.2375    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
    6.4302    1.2375    0.0000 O   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
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  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
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 11  7  2  0  0  0  0
 12 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  5  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  2  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 13  2  0  0  0  0
 20 17  1  0  0  0  0
 21 12  1  0  0  0  0
 21 18  2  0  0  0  0
 22 11  1  0  0  0  0
 22 19  2  0  0  0  0
 23 17  2  0  0  0  0
 23 18  1  0  0  0  0
 24 16  2  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 25  2  0  0  0  0
 30 24  1  0  0  0  0
 30 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033611

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=CC(=C1O)C1=CC2=C(OC1=O)C(CC=C(C)C)=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O5/c1-14(2)5-8-18-21(26)12-10-17(23(18)28)20-13-16-7-11-22(27)19(9-6-15(3)4)24(16)30-25(20)29/h5-7,10-13,26-28H,8-9H2,1-4H3

> <INCHI_KEY>
UAGJZOLUSRCDEP-UHFFFAOYSA-N

> <FORMULA>
C25H26O5

> <MOLECULAR_WEIGHT>
406.4709

> <EXACT_MASS>
406.178023942

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.55932340899544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
4.97

> <JCHEM_LOGP>
5.997885444333334

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.384491068075748

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.503615123970483

> <JCHEM_PKA_STRONGEST_BASIC>
-5.746315475050449

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
120.42899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.67e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-7-hydroxy-8-(3-methylbut-2-en-1-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033611
     RDKit          3D
Licocoumarin A
 56 58  0  0  0  0  0  0  0  0999 V2000
    4.9414   -0.2608    1.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625    0.8276    1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7373    1.5316    2.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7596    1.2508   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    0.8216   -1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.2509   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4883   -1.5587   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8392   -1.7959   -1.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477   -2.6329   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -2.3846   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -1.1243   -0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3305   -0.8528   -0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    0.0461   -1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418    0.2856   -1.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3063    1.1619   -2.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586    1.3918   -2.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702    0.6761   -1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7202    0.9035   -1.4828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431   -0.1980   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4987   -0.9526    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -0.0358    1.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0479    0.1335    1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1564   -0.5942    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3240    1.0740    3.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615   -0.4050   -0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7883   -1.2640    0.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947   -1.4853   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0711   -2.3064    0.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6582   -0.0530   -1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942    1.1973   -1.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046   -0.1830    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698   -0.0702    2.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -1.2498    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1133    1.8114    3.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0744    2.4641    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5351    0.8219    2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4867    2.1001   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7630    0.5600   -2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    1.6977   -1.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454   -1.0797   -1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530   -3.6374   -0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294   -3.2269   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3072    0.5732   -2.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6946    1.6864   -3.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1729    2.0893   -3.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1558    1.5549   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982   -1.8192    0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4265   -1.2984   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9967    0.5286    1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4747   -0.2138    0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8892   -1.6746    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0576   -0.5044    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6929    0.7780    3.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3747    1.0024    3.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1281    2.1245    2.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6258    2.0187   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 19 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 11 29  2  0
 29 30  1  0
 29  6  1  0
 27 12  1  0
 25 14  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 30 56  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       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    8   14                                                       
CONECT    6    9   15                                                       
CONECT    7   11   16                                                       
CONECT    8    5   18                                                       
CONECT    9    6   19                                                       
CONECT   10   12   17                                                       
CONECT   11    7   22                                                       
CONECT   12   10   21                                                       
CONECT   13   16   20                                                       
CONECT   14    1    2    5                                                  
CONECT   15    3    4    6                                                  
CONECT   16    7   13   24                                                  
CONECT   17   10   20   23                                                  
CONECT   18    8   21   23                                                  
CONECT   19    9   22   24                                                  
CONECT   20   13   17   25                                                  
CONECT   21   12   18   26                                                  
CONECT   22   11   19   27                                                  
CONECT   23   17   18   28                                                  
CONECT   24   16   19   30                                                  
CONECT   25   20   29   30                                                  
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   23                                                            
CONECT   29   25                                                            
CONECT   30   24   25                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0033611
HETATM    1  C1  UNL     1       4.941  -0.261   1.769  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.762   0.828   1.171  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.737   1.532   2.136  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.760   1.251  -0.053  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.989   0.822  -1.195  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.013  -0.251  -1.079  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.488  -1.559  -1.033  1.00  0.00           C  
HETATM    8  O1  UNL     1       5.839  -1.796  -1.063  1.00  0.00           O  
HETATM    9  C8  UNL     1       3.648  -2.633  -0.958  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.306  -2.385  -0.929  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.759  -1.124  -0.970  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.331  -0.853  -0.939  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.285   0.046  -1.804  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.642   0.286  -1.753  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.306   1.162  -2.581  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.659   1.392  -2.519  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.370   0.676  -1.546  1.00  0.00           C  
HETATM   18  O2  UNL     1      -5.720   0.903  -1.483  1.00  0.00           O  
HETATM   19  C17 UNL     1      -3.743  -0.198  -0.713  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.499  -0.953   0.317  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.810  -0.036   1.438  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.048   0.134   1.863  1.00  0.00           C  
HETATM   23  C21 UNL     1      -7.156  -0.594   1.227  1.00  0.00           C  
HETATM   24  C22 UNL     1      -6.324   1.074   3.001  1.00  0.00           C  
HETATM   25  C23 UNL     1      -2.362  -0.405  -0.807  1.00  0.00           C  
HETATM   26  O3  UNL     1      -1.788  -1.264   0.023  1.00  0.00           O  
HETATM   27  C24 UNL     1      -0.495  -1.485  -0.033  1.00  0.00           C  
HETATM   28  O4  UNL     1       0.071  -2.306   0.756  1.00  0.00           O  
HETATM   29  C25 UNL     1       2.658  -0.053  -1.047  1.00  0.00           C  
HETATM   30  O5  UNL     1       2.094   1.197  -1.085  1.00  0.00           O  
HETATM   31  H1  UNL     1       3.905  -0.183   1.431  1.00  0.00           H  
HETATM   32  H2  UNL     1       4.870  -0.070   2.898  1.00  0.00           H  
HETATM   33  H3  UNL     1       5.402  -1.250   1.618  1.00  0.00           H  
HETATM   34  H4  UNL     1       6.113   1.811   3.016  1.00  0.00           H  
HETATM   35  H5  UNL     1       7.074   2.464   1.665  1.00  0.00           H  
HETATM   36  H6  UNL     1       7.535   0.822   2.394  1.00  0.00           H  
HETATM   37  H7  UNL     1       6.487   2.100  -0.250  1.00  0.00           H  
HETATM   38  H8  UNL     1       5.763   0.560  -2.013  1.00  0.00           H  
HETATM   39  H9  UNL     1       4.463   1.698  -1.672  1.00  0.00           H  
HETATM   40  H10 UNL     1       6.545  -1.080  -1.115  1.00  0.00           H  
HETATM   41  H11 UNL     1       4.053  -3.637  -0.924  1.00  0.00           H  
HETATM   42  H12 UNL     1       1.629  -3.227  -0.870  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.307   0.573  -2.537  1.00  0.00           H  
HETATM   44  H14 UNL     1      -1.695   1.686  -3.315  1.00  0.00           H  
HETATM   45  H15 UNL     1      -4.173   2.089  -3.181  1.00  0.00           H  
HETATM   46  H16 UNL     1      -6.156   1.555  -2.112  1.00  0.00           H  
HETATM   47  H17 UNL     1      -3.898  -1.819   0.649  1.00  0.00           H  
HETATM   48  H18 UNL     1      -5.427  -1.298  -0.170  1.00  0.00           H  
HETATM   49  H19 UNL     1      -3.997   0.529   1.943  1.00  0.00           H  
HETATM   50  H20 UNL     1      -7.475  -0.214   0.242  1.00  0.00           H  
HETATM   51  H21 UNL     1      -6.889  -1.675   1.172  1.00  0.00           H  
HETATM   52  H22 UNL     1      -8.058  -0.504   1.879  1.00  0.00           H  
HETATM   53  H23 UNL     1      -5.693   0.778   3.856  1.00  0.00           H  
HETATM   54  H24 UNL     1      -7.375   1.002   3.328  1.00  0.00           H  
HETATM   55  H25 UNL     1      -6.128   2.125   2.699  1.00  0.00           H  
HETATM   56  H26 UNL     1       2.626   2.019  -1.129  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3    4    4
CONECT    3   34   35   36
CONECT    4    5   37
CONECT    5    6   38   39
CONECT    6    7    7   29
CONECT    7    8    9
CONECT    8   40
CONECT    9   10   10   41
CONECT   10   11   42
CONECT   11   12   29   29
CONECT   12   13   13   27
CONECT   13   14   43
CONECT   14   15   15   25
CONECT   15   16   44
CONECT   16   17   17   45
CONECT   17   18   19
CONECT   18   46
CONECT   19   20   25   25
CONECT   20   21   47   48
CONECT   21   22   22   49
CONECT   22   23   24
CONECT   23   50   51   52
CONECT   24   53   54   55
CONECT   25   26
CONECT   26   27
CONECT   27   28   28
CONECT   29   30
CONECT   30   56
END

HMDB0033611
     RDKit          3D
Licocoumarin A
 56 58  0  0  0  0  0  0  0  0999 V2000
    4.9414   -0.2608    1.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625    0.8276    1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7373    1.5316    2.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7596    1.2508   -0.0527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    0.8216   -1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.2509   -1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4883   -1.5587   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8392   -1.7959   -1.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477   -2.6329   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3059   -2.3846   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7591   -1.1243   -0.9703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3305   -0.8528   -0.9393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    0.0461   -1.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418    0.2856   -1.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3063    1.1619   -2.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586    1.3918   -2.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702    0.6761   -1.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7202    0.9035   -1.4828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431   -0.1980   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4987   -0.9526    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8103   -0.0358    1.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0479    0.1335    1.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1564   -0.5942    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3240    1.0740    3.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615   -0.4050   -0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7883   -1.2640    0.0233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947   -1.4853   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0711   -2.3064    0.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6582   -0.0530   -1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0942    1.1973   -1.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046   -0.1830    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8698   -0.0702    2.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4022   -1.2498    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1133    1.8114    3.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0744    2.4641    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5351    0.8219    2.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4867    2.1001   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7630    0.5600   -2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    1.6977   -1.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454   -1.0797   -1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0530   -3.6374   -0.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294   -3.2269   -0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3072    0.5732   -2.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6946    1.6864   -3.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1729    2.0893   -3.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1558    1.5549   -2.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982   -1.8192    0.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4265   -1.2984   -0.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9967    0.5286    1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4747   -0.2138    0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8892   -1.6746    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0576   -0.5044    1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6929    0.7780    3.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3747    1.0024    3.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1281    2.1245    2.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6258    2.0187   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 19 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 11 29  2  0
 29 30  1  0
 29  6  1  0
 27 12  1  0
 25 14  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 30 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-7-hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one	HMDB
7,2'4'-Trihydroxy-8,3'-diprenyl-3-phenylcoumarin	HMDB

Chemical Formula

C₂₅H₂₆O₅

Average Molecular Weight

406.4709

Monoisotopic Molecular Weight

406.178023942

IUPAC Name

3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Traditional Name

3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-7-hydroxy-8-(3-methylbut-2-en-1-yl)chromen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=CC(=C1O)C1=CC2=C(OC1=O)C(CC=C(C)C)=C(O)C=C2

InChI Identifier

InChI=1S/C25H26O5/c1-14(2)5-8-18-21(26)12-10-17(23(18)28)20-13-16-7-11-22(27)19(9-6-15(3)4)24(16)30-25(20)29/h5-7,10-13,26-28H,8-9H2,1-4H3

InChI Key

UAGJZOLUSRCDEP-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
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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
Water Solubility	0.0027 g/L	ALOGPS
logP	4.97	ALOGPS
logP	6	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	7.5	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.43 m³·mol⁻¹	ChemAxon
Polarizability	45.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	199.325	31661259
DarkChem	[M-H]-	192.403	31661259
DeepCCS	[M+H]+	199.694	30932474
DeepCCS	[M-H]-	197.336	30932474
DeepCCS	[M-2H]-	231.115	30932474
DeepCCS	[M+Na]+	206.343	30932474
AllCCS	[M+H]+	202.5	32859911
AllCCS	[M+H-H2O]+	199.8	32859911
AllCCS	[M+NH4]+	205.1	32859911
AllCCS	[M+Na]+	205.8	32859911
AllCCS	[M-H]-	192.9	32859911
AllCCS	[M+Na-2H]-	192.7	32859911
AllCCS	[M+HCOO]-	192.7	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.	9.23 minutes	32390414
Predicted by Siyang on May 30, 2022	16.6744 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.13 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2939.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	352.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	222.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	164.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	792.6 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	646.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1373.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	735.1 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	1469.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	526.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	448.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	226.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	222.4 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	8.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Licocoumarin A	CC(C)=CCC1=C(O)C=CC(=C1O)C1=CC2=C(OC1=O)C(CC=C(C)C)=C(O)C=C2	5029.9	Standard polar	33892256
Licocoumarin A	CC(C)=CCC1=C(O)C=CC(=C1O)C1=CC2=C(OC1=O)C(CC=C(C)C)=C(O)C=C2	3183.9	Standard non polar	33892256
Licocoumarin A	CC(C)=CCC1=C(O)C=CC(=C1O)C1=CC2=C(OC1=O)C(CC=C(C)C)=C(O)C=C2	3623.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Licocoumarin A,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=CC3=CC=C(O)C(CC=C(C)C)=C3OC2=O)=C1O	3443.9	Semi standard non polar	33892256
Licocoumarin A,1TMS,isomer #2	CC(C)=CCC1=C(O)C=CC(C2=CC3=CC=C(O)C(CC=C(C)C)=C3OC2=O)=C1O[Si](C)(C)C	3441.8	Semi standard non polar	33892256
Licocoumarin A,1TMS,isomer #3	CC(C)=CCC1=C(O)C=CC(C2=CC3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3OC2=O)=C1O	3454.5	Semi standard non polar	33892256
Licocoumarin A,2TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=CC3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3OC2=O)=C1O	3345.4	Semi standard non polar	33892256
Licocoumarin A,2TMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=CC3=CC=C(O)C(CC=C(C)C)=C3OC2=O)=C1O[Si](C)(C)C	3358.6	Semi standard non polar	33892256
Licocoumarin A,2TMS,isomer #3	CC(C)=CCC1=C(O)C=CC(C2=CC3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3OC2=O)=C1O[Si](C)(C)C	3339.6	Semi standard non polar	33892256
Licocoumarin A,3TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2=CC3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3OC2=O)=C1O[Si](C)(C)C	3337.3	Semi standard non polar	33892256
Licocoumarin A,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=CC3=CC=C(O)C(CC=C(C)C)=C3OC2=O)=C1O	3708.0	Semi standard non polar	33892256
Licocoumarin A,1TBDMS,isomer #2	CC(C)=CCC1=C(O)C=CC(C2=CC3=CC=C(O)C(CC=C(C)C)=C3OC2=O)=C1O[Si](C)(C)C(C)(C)C	3695.9	Semi standard non polar	33892256
Licocoumarin A,1TBDMS,isomer #3	CC(C)=CCC1=C(O)C=CC(C2=CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3OC2=O)=C1O	3718.1	Semi standard non polar	33892256
Licocoumarin A,2TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3OC2=O)=C1O	3824.8	Semi standard non polar	33892256
Licocoumarin A,2TBDMS,isomer #2	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=CC3=CC=C(O)C(CC=C(C)C)=C3OC2=O)=C1O[Si](C)(C)C(C)(C)C	3819.6	Semi standard non polar	33892256
Licocoumarin A,2TBDMS,isomer #3	CC(C)=CCC1=C(O)C=CC(C2=CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3OC2=O)=C1O[Si](C)(C)C(C)(C)C	3804.5	Semi standard non polar	33892256
Licocoumarin A,3TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2=CC3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3OC2=O)=C1O[Si](C)(C)C(C)(C)C	3947.6	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 - Licocoumarin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-1009000000-086e6efc421a09bfc1fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licocoumarin A GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2000059000-eabc4291757287b64f57	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licocoumarin A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licocoumarin A 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 10V, Positive-QTOF	splash10-0a4i-0018900000-0415d320d3c6e58d626a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 20V, Positive-QTOF	splash10-0kxr-2219100000-1656ecd2c5aac17e49b9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 40V, Positive-QTOF	splash10-014r-8549000000-f84db1a0e020e8620703	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 10V, Negative-QTOF	splash10-0a4i-0012900000-fc9ae0a86b452a4a67d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 20V, Negative-QTOF	splash10-004i-0696400000-c218e1b22757222193f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 40V, Negative-QTOF	splash10-056u-1911000000-e2d1ba3fdf9f534d62ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 10V, Negative-QTOF	splash10-0a4i-0000900000-7b5974fd53d3ffdb29ad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 20V, Negative-QTOF	splash10-0a4i-0005900000-df721b2343b7ab723793	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 40V, Negative-QTOF	splash10-02u1-0349000000-1bf9ff68dfacbfe6f26e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 10V, Positive-QTOF	splash10-0pb9-0047900000-113051cb9b4d75a0eae8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 20V, Positive-QTOF	splash10-0f6y-0093000000-b31cbb43a1dc9c7b3df0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licocoumarin A 40V, Positive-QTOF	splash10-0a5d-1089000000-1a14223682e849460e7d	2021-09-25	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

FDB011699

KNApSAcK ID

C00019315

Chemspider ID

4481889

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5324358

PDB ID

Not Available

ChEBI ID

175257

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Licocoumarin A → 6-({3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-8-(3-methylbut-2-en-1-yl)-2-oxo-2H-chromen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Licocoumarin A → 3,4,5-trihydroxy-6-{3-hydroxy-6-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-2H-chromen-3-yl]-2-(3-methylbut-2-en-1-yl)phenoxy}oxane-2-carboxylic acid	details
Licocoumarin A → 3,4,5-trihydroxy-6-{3-hydroxy-4-[7-hydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-2H-chromen-3-yl]-2-(3-methylbut-2-en-1-yl)phenoxy}oxane-2-carboxylic acid	details

Showing metabocard for Licocoumarin A (HMDB0033611)

MOL for HMDB0033611 (Licocoumarin A)

3D MOL for HMDB0033611 (Licocoumarin A)

3D SDF for HMDB0033611 (Licocoumarin A)

3D-SDF for HMDB0033611 (Licocoumarin A)

PDB for HMDB0033611 (Licocoumarin A)

3D PDB for HMDB0033611 (Licocoumarin A)

SMILES for HMDB0033611 (Licocoumarin A)

INCHI for HMDB0033611 (Licocoumarin A)

Structure for HMDB0033611 (Licocoumarin A)

3D Structure for HMDB0033611 (Licocoumarin A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions