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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:58:35 UTC

Update Date

2022-03-07 02:54:01 UTC

HMDB ID

HMDB0034183

Secondary Accession Numbers

HMDB34183

Metabolite Identification

Common Name

Licoricidin

Description

Licoricidin belongs to the class of organic compounds known as 5-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C5 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Licoricidin has been detected, but not quantified in, several different foods, such as herbs and spices, red tea, teas (Camellia sinensis), herbal tea, and black tea. This could make licoricidin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licoricidin.

Structure

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


  Mrv0541 05061307382D          

 31 33  0  0  0  0            999 V2000
   -5.0013    1.2375    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
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
   -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
   -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
   -1.4289    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
    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
   -0.7145    1.2375    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
    3.5724    3.7125    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    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
    0.7145    2.0625    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
    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
   -2.1434    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
   -3.5724    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
   -2.1434    1.2375    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
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  2  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  6  2  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 16  7  2  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 20  9  1  0  0  0  0
 21 12  1  0  0  0  0
 22 11  1  0  0  0  0
 22 19  2  0  0  0  0
 23 13  2  0  0  0  0
 23 20  1  0  0  0  0
 24 13  1  0  0  0  0
 24 21  2  0  0  0  0
 25 18  2  0  0  0  0
 25 19  1  0  0  0  0
 26 20  2  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  1  0  0  0  0
 30  5  1  0  0  0  0
 30 26  1  0  0  0  0
 31 14  1  0  0  0  0
 31 24  1  0  0  0  0
M  END

HMDB0034183
     RDKit          3D
Licoricidin
 63 65  0  0  0  0  0  0  0  0999 V2000
   -2.5389    2.2830    1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4214    0.9079    1.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369   -0.0289    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8214   -0.6520    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0119   -0.2628    1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6330    0.9456    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9165    0.9372    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7401   -0.2501    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5696    2.1084   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9670   -1.5837   -0.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1760   -2.2100   -1.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505   -1.9051   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6277   -1.3021   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5188   -0.3766   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583    0.2738    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846    0.1252   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9939   -0.7177   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874   -1.6632    0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361   -2.4374    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1106   -2.2433    0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1174   -3.0291    1.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3337   -1.3181   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7647   -1.0664   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4036   -0.2347    0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9206    0.9484    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091    1.5419   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5121    1.7395    1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.5608   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080    0.3414   -1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -0.4775   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704   -1.5723   -1.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    2.5218    0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554    2.7112    1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976    2.8931    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7290   -1.0920    0.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205   -0.0118    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0896    1.8511    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4759   -1.1575   -0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8351   -0.0343    0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5565   -0.4969    1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5946    2.9284    0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5784    1.8415   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9555    2.5018   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2568   -2.8878   -1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9131   -2.6184   -2.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567    1.3849    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370   -0.0827    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891    1.1242   -1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -1.8689    1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6239   -3.1672    1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0884   -2.9669    1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7672   -0.4717   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3005   -2.0010   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4328   -0.6414    1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4306    0.8525   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188    1.7972   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5155    2.4772   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0026    2.6623    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1827    1.0869    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6723    2.1175    2.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9237    0.9200   -2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940   -0.7708   -2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042    0.3370   -2.7222 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  3
 25 26  1  0
 25 27  1  0
 22 28  2  0
 28 29  1  0
 16 30  1  0
 30 31  1  0
 14  3  1  0
 28 17  1  0
 31 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  0
 12 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 21 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 30 62  1  0
 30 63  1  0
M  END


  Mrv0541 05061307382D          

 31 33  0  0  0  0            999 V2000
   -5.0013    1.2375    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
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
   -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
   -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
   -1.4289    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
    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
   -0.7145    1.2375    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
    3.5724    3.7125    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    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
    0.7145    2.0625    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
    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
   -2.1434    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
   -3.5724    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
   -2.1434    1.2375    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
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  2  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  6  2  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 16  7  2  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 10  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 20  9  1  0  0  0  0
 21 12  1  0  0  0  0
 22 11  1  0  0  0  0
 22 19  2  0  0  0  0
 23 13  2  0  0  0  0
 23 20  1  0  0  0  0
 24 13  1  0  0  0  0
 24 21  2  0  0  0  0
 25 18  2  0  0  0  0
 25 19  1  0  0  0  0
 26 20  2  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  1  0  0  0  0
 30  5  1  0  0  0  0
 30 26  1  0  0  0  0
 31 14  1  0  0  0  0
 31 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034183

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O5/c1-15(2)6-8-19-22(27)11-10-18(25(19)29)17-12-21-24(31-14-17)13-23(28)20(26(21)30-5)9-7-16(3)4/h6-7,10-11,13,17,27-29H,8-9,12,14H2,1-5H3

> <INCHI_KEY>
GBRZTUJCDFSIHM-UHFFFAOYSA-N

> <FORMULA>
C26H32O5

> <MOLECULAR_WEIGHT>
424.5293

> <EXACT_MASS>
424.224974134

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.29831908289789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

> <ALOGPS_LOGP>
4.85

> <JCHEM_LOGP>
6.187575288666667

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.76218091855417

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.14483206534112

> <JCHEM_PKA_STRONGEST_BASIC>
-4.560864515342554

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
125.88989999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034183
     RDKit          3D
Licoricidin
 63 65  0  0  0  0  0  0  0  0999 V2000
   -2.5389    2.2830    1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4214    0.9079    1.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369   -0.0289    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8214   -0.6520    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0119   -0.2628    1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6330    0.9456    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9165    0.9372    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7401   -0.2501    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5696    2.1084   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9670   -1.5837   -0.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1760   -2.2100   -1.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505   -1.9051   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6277   -1.3021   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5188   -0.3766   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583    0.2738    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846    0.1252   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9939   -0.7177   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874   -1.6632    0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361   -2.4374    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1106   -2.2433    0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1174   -3.0291    1.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3337   -1.3181   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7647   -1.0664   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4036   -0.2347    0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9206    0.9484    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091    1.5419   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5121    1.7395    1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.5608   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080    0.3414   -1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -0.4775   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704   -1.5723   -1.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    2.5218    0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554    2.7112    1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976    2.8931    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7290   -1.0920    0.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205   -0.0118    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0896    1.8511    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4759   -1.1575   -0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8351   -0.0343    0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5565   -0.4969    1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5946    2.9284    0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5784    1.8415   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9555    2.5018   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2568   -2.8878   -1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9131   -2.6184   -2.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567    1.3849    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370   -0.0827    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891    1.1242   -1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -1.8689    1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6239   -3.1672    1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0884   -2.9669    1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7672   -0.4717   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3005   -2.0010   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4328   -0.6414    1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4306    0.8525   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188    1.7972   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5155    2.4772   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0026    2.6623    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1827    1.0869    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6723    2.1175    2.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9237    0.9200   -2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940   -0.7708   -2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042    0.3370   -2.7222 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  3
 25 26  1  0
 25 27  1  0
 22 28  2  0
 28 29  1  0
 16 30  1  0
 30 31  1  0
 14  3  1  0
 28 17  1  0
 31 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  0
 12 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 21 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 30 62  1  0
 30 63  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   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   3.850   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      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667   6.160   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
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5   30                                                            
CONECT    6    8   15                                                       
CONECT    7    9   16                                                       
CONECT    8    6   19                                                       
CONECT    9    7   20                                                       
CONECT   10   11   18                                                       
CONECT   11   10   22                                                       
CONECT   12   17   21                                                       
CONECT   13   23   24                                                       
CONECT   14   17   31                                                       
CONECT   15    1    2    6                                                  
CONECT   16    3    4    7                                                  
CONECT   17   12   14   18                                                  
CONECT   18   10   17   25                                                  
CONECT   19    8   22   25                                                  
CONECT   20    9   23   26                                                  
CONECT   21   12   24   26                                                  
CONECT   22   11   19   27                                                  
CONECT   23   13   20   28                                                  
CONECT   24   13   21   31                                                  
CONECT   25   18   19   29                                                  
CONECT   26   20   21   30                                                  
CONECT   27   22                                                            
CONECT   28   23                                                            
CONECT   29   25                                                            
CONECT   30    5   26                                                       
CONECT   31   14   24                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0034183
HETATM    1  C1  UNL     1      -2.539   2.283   1.279  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.421   0.908   1.518  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.637  -0.029   0.533  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.821  -0.652   0.248  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.012  -0.263   1.040  1.00  0.00           C  
HETATM    6  C5  UNL     1      -5.633   0.946   0.439  1.00  0.00           C  
HETATM    7  C6  UNL     1      -6.917   0.937   0.182  1.00  0.00           C  
HETATM    8  C7  UNL     1      -7.740  -0.250   0.489  1.00  0.00           C  
HETATM    9  C8  UNL     1      -7.570   2.108  -0.435  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.967  -1.584  -0.751  1.00  0.00           C  
HETATM   11  O2  UNL     1      -5.176  -2.210  -1.027  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.851  -1.905  -1.506  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.628  -1.302  -1.257  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.519  -0.377  -0.252  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.258   0.274   0.065  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.885   0.125  -0.855  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.994  -0.718  -0.283  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.787  -1.663   0.690  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.836  -2.437   1.214  1.00  0.00           C  
HETATM   20  C18 UNL     1       4.111  -2.243   0.739  1.00  0.00           C  
HETATM   21  O3  UNL     1       5.117  -3.029   1.286  1.00  0.00           O  
HETATM   22  C19 UNL     1       4.334  -1.318  -0.218  1.00  0.00           C  
HETATM   23  C20 UNL     1       5.765  -1.066  -0.629  1.00  0.00           C  
HETATM   24  C21 UNL     1       6.404  -0.235   0.449  1.00  0.00           C  
HETATM   25  C22 UNL     1       6.921   0.948   0.223  1.00  0.00           C  
HETATM   26  C23 UNL     1       6.909   1.542  -1.139  1.00  0.00           C  
HETATM   27  C24 UNL     1       7.512   1.739   1.352  1.00  0.00           C  
HETATM   28  C25 UNL     1       3.302  -0.561  -0.734  1.00  0.00           C  
HETATM   29  O4  UNL     1       3.608   0.341  -1.701  1.00  0.00           O  
HETATM   30  C26 UNL     1       0.418  -0.477  -2.179  1.00  0.00           C  
HETATM   31  O5  UNL     1      -0.470  -1.572  -1.975  1.00  0.00           O  
HETATM   32  H1  UNL     1      -2.628   2.522   0.181  1.00  0.00           H  
HETATM   33  H2  UNL     1      -3.455   2.711   1.747  1.00  0.00           H  
HETATM   34  H3  UNL     1      -1.698   2.893   1.661  1.00  0.00           H  
HETATM   35  H4  UNL     1      -5.729  -1.092   0.990  1.00  0.00           H  
HETATM   36  H5  UNL     1      -4.720  -0.012   2.086  1.00  0.00           H  
HETATM   37  H6  UNL     1      -5.090   1.851   0.184  1.00  0.00           H  
HETATM   38  H7  UNL     1      -7.476  -1.157  -0.081  1.00  0.00           H  
HETATM   39  H8  UNL     1      -8.835  -0.034   0.405  1.00  0.00           H  
HETATM   40  H9  UNL     1      -7.556  -0.497   1.562  1.00  0.00           H  
HETATM   41  H10 UNL     1      -7.595   2.928   0.300  1.00  0.00           H  
HETATM   42  H11 UNL     1      -8.578   1.842  -0.815  1.00  0.00           H  
HETATM   43  H12 UNL     1      -6.955   2.502  -1.297  1.00  0.00           H  
HETATM   44  H13 UNL     1      -5.257  -2.888  -1.760  1.00  0.00           H  
HETATM   45  H14 UNL     1      -2.913  -2.618  -2.288  1.00  0.00           H  
HETATM   46  H15 UNL     1      -0.457   1.385   0.280  1.00  0.00           H  
HETATM   47  H16 UNL     1       0.037  -0.083   1.097  1.00  0.00           H  
HETATM   48  H17 UNL     1       1.289   1.124  -1.073  1.00  0.00           H  
HETATM   49  H18 UNL     1       0.825  -1.869   1.096  1.00  0.00           H  
HETATM   50  H19 UNL     1       2.624  -3.167   1.977  1.00  0.00           H  
HETATM   51  H20 UNL     1       6.088  -2.967   1.007  1.00  0.00           H  
HETATM   52  H21 UNL     1       5.767  -0.472  -1.559  1.00  0.00           H  
HETATM   53  H22 UNL     1       6.300  -2.001  -0.812  1.00  0.00           H  
HETATM   54  H23 UNL     1       6.433  -0.641   1.459  1.00  0.00           H  
HETATM   55  H24 UNL     1       7.431   0.853  -1.847  1.00  0.00           H  
HETATM   56  H25 UNL     1       5.919   1.797  -1.513  1.00  0.00           H  
HETATM   57  H26 UNL     1       7.516   2.477  -1.149  1.00  0.00           H  
HETATM   58  H27 UNL     1       8.003   2.662   0.980  1.00  0.00           H  
HETATM   59  H28 UNL     1       8.183   1.087   1.935  1.00  0.00           H  
HETATM   60  H29 UNL     1       6.672   2.118   2.008  1.00  0.00           H  
HETATM   61  H30 UNL     1       2.924   0.920  -2.137  1.00  0.00           H  
HETATM   62  H31 UNL     1       1.294  -0.771  -2.797  1.00  0.00           H  
HETATM   63  H32 UNL     1      -0.104   0.337  -2.722  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   10
CONECT    5    6   35   36
CONECT    6    7    7   37
CONECT    7    8    9
CONECT    8   38   39   40
CONECT    9   41   42   43
CONECT   10   11   12   12
CONECT   11   44
CONECT   12   13   45
CONECT   13   14   14   31
CONECT   14   15
CONECT   15   16   46   47
CONECT   16   17   30   48
CONECT   17   18   18   28
CONECT   18   19   49
CONECT   19   20   20   50
CONECT   20   21   22
CONECT   21   51
CONECT   22   23   28   28
CONECT   23   24   52   53
CONECT   24   25   25   54
CONECT   25   26   27
CONECT   26   55   56   57
CONECT   27   58   59   60
CONECT   28   29
CONECT   29   61
CONECT   30   31   62   63
END

HMDB0034183
     RDKit          3D
Licoricidin
 63 65  0  0  0  0  0  0  0  0999 V2000
   -2.5389    2.2830    1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4214    0.9079    1.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6369   -0.0289    0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8214   -0.6520    0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0119   -0.2628    1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6330    0.9456    0.4388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9165    0.9372    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7401   -0.2501    0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5696    2.1084   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9670   -1.5837   -0.7505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1760   -2.2100   -1.0265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505   -1.9051   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6277   -1.3021   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5188   -0.3766   -0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583    0.2738    0.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8846    0.1252   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9939   -0.7177   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7874   -1.6632    0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361   -2.4374    1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1106   -2.2433    0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1174   -3.0291    1.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3337   -1.3181   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7647   -1.0664   -0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4036   -0.2347    0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9206    0.9484    0.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091    1.5419   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5121    1.7395    1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.5608   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6080    0.3414   -1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4175   -0.4775   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4704   -1.5723   -1.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281    2.5218    0.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554    2.7112    1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6976    2.8931    1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7290   -1.0920    0.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7205   -0.0118    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0896    1.8511    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4759   -1.1575   -0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8351   -0.0343    0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5565   -0.4969    1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5946    2.9284    0.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5784    1.8415   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9555    2.5018   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2568   -2.8878   -1.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9131   -2.6184   -2.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4567    1.3849    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370   -0.0827    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891    1.1242   -1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -1.8689    1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6239   -3.1672    1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0884   -2.9669    1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7672   -0.4717   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3005   -2.0010   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4328   -0.6414    1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4306    0.8525   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9188    1.7972   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5155    2.4772   -1.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0026    2.6623    0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1827    1.0869    1.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6723    2.1175    2.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9237    0.9200   -2.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940   -0.7708   -2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042    0.3370   -2.7222 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  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  3
 25 26  1  0
 25 27  1  0
 22 28  2  0
 28 29  1  0
 16 30  1  0
 30 31  1  0
 14  3  1  0
 28 17  1  0
 31 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 11 44  1  0
 12 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 18 49  1  0
 19 50  1  0
 21 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 29 61  1  0
 30 62  1  0
 30 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4',7-Trihydroxy-5-methoxy-3',6-diprenylisoflavan	HMDB
5,2',4'-Trihydroxy-7-methoxy-6,3'-diprenylisoflavan	HMDB

Chemical Formula

C₂₆H₃₂O₅

Average Molecular Weight

424.5293

Monoisotopic Molecular Weight

424.224974134

IUPAC Name

4-[7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

Traditional Name

4-[7-hydroxy-5-methoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol

CAS Registry Number

30508-27-1

SMILES

COC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C1

InChI Identifier

InChI=1S/C26H32O5/c1-15(2)6-8-19-22(27)11-10-18(25(19)29)17-12-21-24(31-14-17)13-23(28)20(26(21)30-5)9-7-16(3)4/h6-7,10-11,13,17,27-29H,8-9,12,14H2,1-5H3

InChI Key

GBRZTUJCDFSIHM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C5 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

5-O-methylated isoflavonoids

Alternative Parents

Substituents

5-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Isoflavanol
Isoflavan
Chromane
Benzopyran
1-benzopyran
Anisole
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034183)

Cellular substructure

Membrane (HMDB: HMDB0034183)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034183)

Source

Exogenous

Food

Food (HMDB: HMDB0034183)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034183)

Not Available

Nutrient (HMDB: HMDB0034183)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	154 - 156 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0013 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	0.0027 g/L	ALOGPS
logP	4.85	ALOGPS
logP	6.19	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	125.89 m³·mol⁻¹	ChemAxon
Polarizability	48.3 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	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	200.676	31661259
DarkChem	[M-H]-	198.899	31661259
DeepCCS	[M+H]+	208.084	30932474
DeepCCS	[M-H]-	205.726	30932474
DeepCCS	[M-2H]-	238.61	30932474
DeepCCS	[M+Na]+	214.178	30932474
AllCCS	[M+H]+	207.5	32859911
AllCCS	[M+H-H2O]+	205.0	32859911
AllCCS	[M+NH4]+	209.9	32859911
AllCCS	[M+Na]+	210.6	32859911
AllCCS	[M-H]-	204.6	32859911
AllCCS	[M+Na-2H]-	205.0	32859911
AllCCS	[M+HCOO]-	205.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Licoricidin	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C1	4612.9	Standard polar	33892256
Licoricidin	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C1	3354.2	Standard non polar	33892256
Licoricidin	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(CO2)C1=C(O)C(CC=C(C)C)=C(O)C=C1	3773.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Licoricidin,1TMS,isomer #1	COC1=C2CC(C3=CC=C(O)C(CC=C(C)C)=C3O)COC2=CC(O[Si](C)(C)C)=C1CC=C(C)C	3528.0	Semi standard non polar	33892256
Licoricidin,1TMS,isomer #2	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C)CO2	3473.6	Semi standard non polar	33892256
Licoricidin,1TMS,isomer #3	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O)CO2	3509.5	Semi standard non polar	33892256
Licoricidin,2TMS,isomer #1	COC1=C2CC(C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3O)COC2=CC(O[Si](C)(C)C)=C1CC=C(C)C	3409.3	Semi standard non polar	33892256
Licoricidin,2TMS,isomer #2	COC1=C2CC(C3=CC=C(O)C(CC=C(C)C)=C3O[Si](C)(C)C)COC2=CC(O[Si](C)(C)C)=C1CC=C(C)C	3385.6	Semi standard non polar	33892256
Licoricidin,2TMS,isomer #3	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C)CO2	3388.0	Semi standard non polar	33892256
Licoricidin,3TMS,isomer #1	COC1=C2CC(C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3O[Si](C)(C)C)COC2=CC(O[Si](C)(C)C)=C1CC=C(C)C	3313.8	Semi standard non polar	33892256
Licoricidin,1TBDMS,isomer #1	COC1=C2CC(C3=CC=C(O)C(CC=C(C)C)=C3O)COC2=CC(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3754.7	Semi standard non polar	33892256
Licoricidin,1TBDMS,isomer #2	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C)CO2	3698.9	Semi standard non polar	33892256
Licoricidin,1TBDMS,isomer #3	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O)CO2	3745.5	Semi standard non polar	33892256
Licoricidin,2TBDMS,isomer #1	COC1=C2CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3O)COC2=CC(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3818.6	Semi standard non polar	33892256
Licoricidin,2TBDMS,isomer #2	COC1=C2CC(C3=CC=C(O)C(CC=C(C)C)=C3O[Si](C)(C)C(C)(C)C)COC2=CC(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3760.8	Semi standard non polar	33892256
Licoricidin,2TBDMS,isomer #3	COC1=C(CC=C(C)C)C(O)=CC2=C1CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C)CO2	3777.2	Semi standard non polar	33892256
Licoricidin,3TBDMS,isomer #1	COC1=C2CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3O[Si](C)(C)C(C)(C)C)COC2=CC(O[Si](C)(C)C(C)(C)C)=C1CC=C(C)C	3863.2	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 - Licoricidin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0api-2219500000-8ec9916e7368bc844fac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licoricidin GC-MS (3 TMS) - 70eV, Positive	splash10-004i-1000049000-7e8098315abcd17050a0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licoricidin 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 - Licoricidin 10V, Positive-QTOF	splash10-0100-0193400000-f13c728fe9aeedfebef6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 20V, Positive-QTOF	splash10-01b9-1292100000-3d93b870275056e3ff76	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 40V, Positive-QTOF	splash10-014r-5952100000-a860eeea3ae0ac080ea4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 10V, Positive-QTOF	splash10-0100-0193400000-f13c728fe9aeedfebef6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 20V, Positive-QTOF	splash10-01b9-1292100000-3d93b870275056e3ff76	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 40V, Positive-QTOF	splash10-014r-5952100000-a860eeea3ae0ac080ea4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 10V, Negative-QTOF	splash10-00di-0040900000-86df565fc8536c36f84c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 20V, Negative-QTOF	splash10-00ba-0593400000-736073b1948a6116c1e7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 40V, Negative-QTOF	splash10-0kdi-0981100000-9ef6b8a5cb02123a5f30	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 10V, Negative-QTOF	splash10-00di-0040900000-86df565fc8536c36f84c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 20V, Negative-QTOF	splash10-00ba-0593400000-736073b1948a6116c1e7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 40V, Negative-QTOF	splash10-0kdi-0981100000-9ef6b8a5cb02123a5f30	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 10V, Positive-QTOF	splash10-004i-0007900000-93f38e5ef16dffb24aea	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 20V, Positive-QTOF	splash10-03di-0209000000-4ce47c01c27872a0d43e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 40V, Positive-QTOF	splash10-0w93-1639100000-f42a2eedc2dcd81490aa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 10V, Negative-QTOF	splash10-00di-0000900000-5b29951e5ffb9123f005	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 20V, Negative-QTOF	splash10-00dl-0009300000-b1f514be9d0f2f0e1c9a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licoricidin 40V, Negative-QTOF	splash10-000i-1319200000-6d7c11d52f4c969ab273	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9845260

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1840991

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.. .

Showing metabocard for Licoricidin (HMDB0034183)

MOL for HMDB0034183 (Licoricidin)

3D MOL for HMDB0034183 (Licoricidin)

3D SDF for HMDB0034183 (Licoricidin)

3D-SDF for HMDB0034183 (Licoricidin)

PDB for HMDB0034183 (Licoricidin)

3D PDB for HMDB0034183 (Licoricidin)

SMILES for HMDB0034183 (Licoricidin)

INCHI for HMDB0034183 (Licoricidin)

Structure for HMDB0034183 (Licoricidin)

3D Structure for HMDB0034183 (Licoricidin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra