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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:58:39 UTC

Update Date

2022-03-07 02:54:01 UTC

HMDB ID

HMDB0034184

Secondary Accession Numbers

HMDB34184

Metabolite Identification

Common Name

Licorisoflavan A

Description

Licorisoflavan A belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, licorisoflavan a is considered to be a flavonoid. Licorisoflavan A has been detected, but not quantified in, herbs and spices. This could make licorisoflavan a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Licorisoflavan A.

Structure

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


  Mrv0541 05061307382D          

 32 34  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
    3.5724    1.2375    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
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  7  2  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
 17  8  2  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 21 10  1  0  0  0  0
 22 13  1  0  0  0  0
 23 12  1  0  0  0  0
 23 20  2  0  0  0  0
 24 14  2  0  0  0  0
 24 21  1  0  0  0  0
 25 14  1  0  0  0  0
 25 22  2  0  0  0  0
 26 19  2  0  0  0  0
 26 20  1  0  0  0  0
 27 21  2  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 26  1  0  0  0  0
 30  5  1  0  0  0  0
 30 24  1  0  0  0  0
 31  6  1  0  0  0  0
 31 27  1  0  0  0  0
 32 15  1  0  0  0  0
 32 25  1  0  0  0  0
M  END

HMDB0034184
     RDKit          3D
Licorisoflavan A
 66 68  0  0  0  0  0  0  0  0999 V2000
   -5.3695    3.2885   -1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119    1.8763   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9705    1.3747   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    2.2183   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012    1.6709    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    0.3105    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -0.5419    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -1.9022    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -2.8161   -0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079    0.0179   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9327   -0.8966   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9513   -0.9014    0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2198   -0.6159    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1084   -0.6653    1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7982   -0.2513   -0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -0.2307    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750    0.6855    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    0.1353    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -1.0489    1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -1.6252    1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.0083    1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664   -1.5810    1.6961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    0.1898    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9134    0.8011    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5333    0.1106   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7283   -0.4181   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6354   -0.4185    0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2532   -1.1021   -2.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824    0.7424    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    1.9125   -0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    2.0394    1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194    2.4885    0.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7438    3.6549   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    3.7553   -0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4084    3.5662   -1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937    3.2894   -0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -3.7876   -0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0123   -3.0711   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -2.4799   -1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5510   -1.9594   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3601   -0.6929   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5329   -1.1832    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5650   -0.3534    2.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8980    0.1221    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6071   -1.6266    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7271    0.8431   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9037   -0.4850   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3621   -0.8268   -1.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -0.4025    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -1.2173    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975    0.7957   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -1.5982    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213   -2.5626    2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967   -2.4517    2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6081    0.6352    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677    1.8889    0.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9327    0.0617   -1.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4900   -1.2479    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5873    0.5767    0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7080   -0.4917   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2959   -1.4126   -1.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6448   -1.9867   -2.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2056   -0.3086   -2.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210    2.4030   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3871    2.7897    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896    1.9251    2.1055 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 23 29  2  0
 29 30  1  0
 17 31  1  0
 31 32  1  0
 10  3  1  0
 29 18  1  0
 32  5  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 30 64  1  0
 31 65  1  0
 31 66  1  0
M  END


  Mrv0541 05061307382D          

 32 34  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
    3.5724    1.2375    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
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    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
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  7  2  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
 17  8  2  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 21 10  1  0  0  0  0
 22 13  1  0  0  0  0
 23 12  1  0  0  0  0
 23 20  2  0  0  0  0
 24 14  2  0  0  0  0
 24 21  1  0  0  0  0
 25 14  1  0  0  0  0
 25 22  2  0  0  0  0
 26 19  2  0  0  0  0
 26 20  1  0  0  0  0
 27 21  2  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29 26  1  0  0  0  0
 30  5  1  0  0  0  0
 30 24  1  0  0  0  0
 31  6  1  0  0  0  0
 31 27  1  0  0  0  0
 32 15  1  0  0  0  0
 32 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034184

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(CC(CO2)C2=C(O)C(CC=C(C)C)=C(O)C=C2)C(OC)=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O5/c1-16(2)7-9-20-23(28)12-11-19(26(20)29)18-13-22-25(32-15-18)14-24(30-5)21(27(22)31-6)10-8-17(3)4/h7-8,11-12,14,18,28-29H,9-10,13,15H2,1-6H3

> <INCHI_KEY>
GDAAEAXMNLVRCZ-UHFFFAOYSA-N

> <FORMULA>
C27H34O5

> <MOLECULAR_WEIGHT>
438.5559

> <EXACT_MASS>
438.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
50.27538956469333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[5,7-dimethoxy-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>
5.31

> <JCHEM_LOGP>
6.333469344666667

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.664505061561455

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.318991034720215

> <JCHEM_PKA_STRONGEST_BASIC>
-4.380578615777177

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
130.37219999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
licorisoflavan A

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034184
     RDKit          3D
Licorisoflavan A
 66 68  0  0  0  0  0  0  0  0999 V2000
   -5.3695    3.2885   -1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119    1.8763   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9705    1.3747   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    2.2183   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012    1.6709    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    0.3105    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -0.5419    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -1.9022    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -2.8161   -0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079    0.0179   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9327   -0.8966   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9513   -0.9014    0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2198   -0.6159    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1084   -0.6653    1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7982   -0.2513   -0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -0.2307    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750    0.6855    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    0.1353    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -1.0489    1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -1.6252    1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.0083    1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664   -1.5810    1.6961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    0.1898    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9134    0.8011    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5333    0.1106   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7283   -0.4181   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6354   -0.4185    0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2532   -1.1021   -2.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824    0.7424    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    1.9125   -0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    2.0394    1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194    2.4885    0.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7438    3.6549   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    3.7553   -0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4084    3.5662   -1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937    3.2894   -0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -3.7876   -0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0123   -3.0711   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -2.4799   -1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5510   -1.9594   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3601   -0.6929   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5329   -1.1832    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5650   -0.3534    2.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8980    0.1221    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6071   -1.6266    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7271    0.8431   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9037   -0.4850   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3621   -0.8268   -1.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -0.4025    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -1.2173    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975    0.7957   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -1.5982    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213   -2.5626    2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967   -2.4517    2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6081    0.6352    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677    1.8889    0.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9327    0.0617   -1.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4900   -1.2479    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5873    0.5767    0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7080   -0.4917   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2959   -1.4126   -1.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6448   -1.9867   -2.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2056   -0.3086   -2.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210    2.4030   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3871    2.7897    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896    1.9251    2.1055 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 23 29  2  0
 29 30  1  0
 17 31  1  0
 31 32  1  0
 10  3  1  0
 29 18  1  0
 32  5  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 30 64  1  0
 31 65  1  0
 31 66  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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.335   6.160   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.668   6.930   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       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   17                                                            
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7    9   16                                                       
CONECT    8   10   17                                                       
CONECT    9    7   20                                                       
CONECT   10    8   21                                                       
CONECT   11   12   19                                                       
CONECT   12   11   23                                                       
CONECT   13   18   22                                                       
CONECT   14   24   25                                                       
CONECT   15   18   32                                                       
CONECT   16    1    2    7                                                  
CONECT   17    3    4    8                                                  
CONECT   18   13   15   19                                                  
CONECT   19   11   18   26                                                  
CONECT   20    9   23   26                                                  
CONECT   21   10   24   27                                                  
CONECT   22   13   25   27                                                  
CONECT   23   12   20   28                                                  
CONECT   24   14   21   30                                                  
CONECT   25   14   22   32                                                  
CONECT   26   19   20   29                                                  
CONECT   27   21   22   31                                                  
CONECT   28   23                                                            
CONECT   29   26                                                            
CONECT   30    5   24                                                       
CONECT   31    6   27                                                       
CONECT   32   15   25                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0034184
HETATM    1  C1  UNL     1      -5.370   3.289  -1.032  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.212   1.876  -0.886  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.971   1.375  -0.459  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.918   2.218  -0.184  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.701   1.671   0.239  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.539   0.310   0.383  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.595  -0.542   0.108  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.468  -1.902   0.241  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.070  -2.816  -0.731  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.808   0.018  -0.315  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.933  -0.897  -0.607  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.951  -0.901   0.481  1.00  0.00           C  
HETATM   13  C11 UNL     1      -7.220  -0.616   0.355  1.00  0.00           C  
HETATM   14  C12 UNL     1      -8.108  -0.665   1.541  1.00  0.00           C  
HETATM   15  C13 UNL     1      -7.798  -0.251  -0.951  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.228  -0.231   0.840  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.875   0.685   0.397  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.204   0.135   0.709  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.267  -1.049   1.403  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.478  -1.625   1.734  1.00  0.00           C  
HETATM   21  C19 UNL     1       4.641  -1.008   1.367  1.00  0.00           C  
HETATM   22  O3  UNL     1       5.866  -1.581   1.696  1.00  0.00           O  
HETATM   23  C20 UNL     1       4.597   0.190   0.665  1.00  0.00           C  
HETATM   24  C21 UNL     1       5.913   0.801   0.296  1.00  0.00           C  
HETATM   25  C22 UNL     1       6.533   0.111  -0.861  1.00  0.00           C  
HETATM   26  C23 UNL     1       7.728  -0.418  -0.812  1.00  0.00           C  
HETATM   27  C24 UNL     1       8.635  -0.419   0.360  1.00  0.00           C  
HETATM   28  C25 UNL     1       8.253  -1.102  -2.059  1.00  0.00           C  
HETATM   29  C26 UNL     1       3.382   0.742   0.347  1.00  0.00           C  
HETATM   30  O4  UNL     1       3.309   1.913  -0.339  1.00  0.00           O  
HETATM   31  C27 UNL     1       0.631   2.039   1.003  1.00  0.00           C  
HETATM   32  O5  UNL     1      -0.619   2.489   0.525  1.00  0.00           O  
HETATM   33  H1  UNL     1      -4.744   3.655  -1.866  1.00  0.00           H  
HETATM   34  H2  UNL     1      -4.968   3.755  -0.092  1.00  0.00           H  
HETATM   35  H3  UNL     1      -6.408   3.566  -1.194  1.00  0.00           H  
HETATM   36  H4  UNL     1      -2.994   3.289  -0.281  1.00  0.00           H  
HETATM   37  H5  UNL     1      -2.600  -3.788  -0.500  1.00  0.00           H  
HETATM   38  H6  UNL     1      -1.012  -3.071  -0.768  1.00  0.00           H  
HETATM   39  H7  UNL     1      -2.369  -2.480  -1.765  1.00  0.00           H  
HETATM   40  H8  UNL     1      -4.551  -1.959  -0.668  1.00  0.00           H  
HETATM   41  H9  UNL     1      -5.360  -0.693  -1.607  1.00  0.00           H  
HETATM   42  H10 UNL     1      -5.533  -1.183   1.472  1.00  0.00           H  
HETATM   43  H11 UNL     1      -7.565  -0.353   2.476  1.00  0.00           H  
HETATM   44  H12 UNL     1      -8.898   0.122   1.404  1.00  0.00           H  
HETATM   45  H13 UNL     1      -8.607  -1.627   1.679  1.00  0.00           H  
HETATM   46  H14 UNL     1      -7.727   0.843  -1.075  1.00  0.00           H  
HETATM   47  H15 UNL     1      -8.904  -0.485  -0.962  1.00  0.00           H  
HETATM   48  H16 UNL     1      -7.362  -0.827  -1.804  1.00  0.00           H  
HETATM   49  H17 UNL     1      -0.232  -0.403   1.935  1.00  0.00           H  
HETATM   50  H18 UNL     1      -0.021  -1.217   0.346  1.00  0.00           H  
HETATM   51  H19 UNL     1       0.798   0.796  -0.705  1.00  0.00           H  
HETATM   52  H20 UNL     1       1.396  -1.598   1.731  1.00  0.00           H  
HETATM   53  H21 UNL     1       3.521  -2.563   2.284  1.00  0.00           H  
HETATM   54  H22 UNL     1       5.897  -2.452   2.206  1.00  0.00           H  
HETATM   55  H23 UNL     1       6.608   0.635   1.178  1.00  0.00           H  
HETATM   56  H24 UNL     1       5.868   1.889   0.180  1.00  0.00           H  
HETATM   57  H25 UNL     1       5.933   0.062  -1.780  1.00  0.00           H  
HETATM   58  H26 UNL     1       8.490  -1.248   1.055  1.00  0.00           H  
HETATM   59  H27 UNL     1       8.587   0.577   0.855  1.00  0.00           H  
HETATM   60  H28 UNL     1       9.708  -0.492  -0.003  1.00  0.00           H  
HETATM   61  H29 UNL     1       9.296  -1.413  -1.946  1.00  0.00           H  
HETATM   62  H30 UNL     1       7.645  -1.987  -2.314  1.00  0.00           H  
HETATM   63  H31 UNL     1       8.206  -0.309  -2.850  1.00  0.00           H  
HETATM   64  H32 UNL     1       4.121   2.403  -0.636  1.00  0.00           H  
HETATM   65  H33 UNL     1       1.387   2.790   0.686  1.00  0.00           H  
HETATM   66  H34 UNL     1       0.590   1.925   2.105  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   36
CONECT    5    6    6   32
CONECT    6    7   16
CONECT    7    8   10   10
CONECT    8    9
CONECT    9   37   38   39
CONECT   10   11
CONECT   11   12   40   41
CONECT   12   13   13   42
CONECT   13   14   15
CONECT   14   43   44   45
CONECT   15   46   47   48
CONECT   16   17   49   50
CONECT   17   18   31   51
CONECT   18   19   19   29
CONECT   19   20   52
CONECT   20   21   21   53
CONECT   21   22   23
CONECT   22   54
CONECT   23   24   29   29
CONECT   24   25   55   56
CONECT   25   26   26   57
CONECT   26   27   28
CONECT   27   58   59   60
CONECT   28   61   62   63
CONECT   29   30
CONECT   30   64
CONECT   31   32   65   66
END

HMDB0034184
     RDKit          3D
Licorisoflavan A
 66 68  0  0  0  0  0  0  0  0999 V2000
   -5.3695    3.2885   -1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119    1.8763   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9705    1.3747   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    2.2183   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7012    1.6709    0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    0.3105    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -0.5419    0.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -1.9022    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -2.8161   -0.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8079    0.0179   -0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9327   -0.8966   -0.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9513   -0.9014    0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2198   -0.6159    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1084   -0.6653    1.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7982   -0.2513   -0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -0.2307    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750    0.6855    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038    0.1353    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -1.0489    1.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783   -1.6252    1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.0083    1.3668 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664   -1.5810    1.6961 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5971    0.1898    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9134    0.8011    0.2964 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5333    0.1106   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7283   -0.4181   -0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6354   -0.4185    0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2532   -1.1021   -2.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3824    0.7424    0.3470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094    1.9125   -0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    2.0394    1.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6194    2.4885    0.5248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7438    3.6549   -1.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9679    3.7553   -0.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4084    3.5662   -1.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9937    3.2894   -0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -3.7876   -0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0123   -3.0711   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3687   -2.4799   -1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5510   -1.9594   -0.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3601   -0.6929   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5329   -1.1832    1.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5650   -0.3534    2.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8980    0.1221    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6071   -1.6266    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7271    0.8431   -1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9037   -0.4850   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3621   -0.8268   -1.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -0.4025    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0209   -1.2173    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7975    0.7957   -0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -1.5982    1.7311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5213   -2.5626    2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8967   -2.4517    2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6081    0.6352    1.1780 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8677    1.8889    0.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9327    0.0617   -1.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4900   -1.2479    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5873    0.5767    0.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7080   -0.4917   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2959   -1.4126   -1.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6448   -1.9867   -2.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2056   -0.3086   -2.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1210    2.4030   -0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3871    2.7897    0.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5896    1.9251    2.1055 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  3
 26 27  1  0
 26 28  1  0
 23 29  2  0
 29 30  1  0
 17 31  1  0
 31 32  1  0
 10  3  1  0
 29 18  1  0
 32  5  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 19 52  1  0
 20 53  1  0
 22 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 27 58  1  0
 27 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 30 64  1  0
 31 65  1  0
 31 66  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-2',4'-Dihydroxy-5,7-dimethoxy-6,3'-diprenylisoflavan	HMDB
2',4'-Dihydroxy-5,7-dimethoxy-3',6-diprenylisoflavan	HMDB
5-O-Methyllicoricidin	HMDB
7-O-Methylicoricidin	HMDB
7-O-Methyllicoricidin	HMDB
LicorIIsoflavan a	HMDB
Licorisoflavan a	MeSH

Chemical Formula

C₂₇H₃₄O₅

Average Molecular Weight

438.5559

Monoisotopic Molecular Weight

438.240624198

IUPAC Name

4-[5,7-dimethoxy-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

licorisoflavan A

CAS Registry Number

129314-37-0

SMILES

COC1=CC2=C(CC(CO2)C2=C(O)C(CC=C(C)C)=C(O)C=C2)C(OC)=C1CC=C(C)C

InChI Identifier

InChI=1S/C27H34O5/c1-16(2)7-9-20-23(28)12-11-19(26(20)29)18-13-22-25(32-15-18)14-24(30-5)21(27(22)31-6)10-8-17(3)4/h7-8,11-12,14,18,28-29H,9-10,13,15H2,1-6H3

InChI Key

GDAAEAXMNLVRCZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 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

7-O-methylated isoflavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080046 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034184)

Membrane (HMDB: HMDB0034184)
Cell membrane (HMDB: HMDB0034184)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034184)

Source

Exogenous

Food

Food (HMDB: HMDB0034184)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034184)

Not Available

Nutrient (HMDB: HMDB0034184)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	65 - 67 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00034 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	0.002 g/L	ALOGPS
logP	5.31	ALOGPS
logP	6.33	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.37 m³·mol⁻¹	ChemAxon
Polarizability	50.28 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]+	203.283	31661259
DarkChem	[M-H]-	205.802	31661259
DeepCCS	[M+H]+	209.443	30932474
DeepCCS	[M-H]-	207.085	30932474
DeepCCS	[M-2H]-	239.972	30932474
DeepCCS	[M+Na]+	215.537	30932474
AllCCS	[M+H]+	210.3	32859911
AllCCS	[M+H-H2O]+	207.9	32859911
AllCCS	[M+NH4]+	212.6	32859911
AllCCS	[M+Na]+	213.3	32859911
AllCCS	[M-H]-	208.7	32859911
AllCCS	[M+Na-2H]-	209.3	32859911
AllCCS	[M+HCOO]-	210.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Licorisoflavan A	COC1=CC2=C(CC(CO2)C2=C(O)C(CC=C(C)C)=C(O)C=C2)C(OC)=C1CC=C(C)C	4470.1	Standard polar	33892256
Licorisoflavan A	COC1=CC2=C(CC(CO2)C2=C(O)C(CC=C(C)C)=C(O)C=C2)C(OC)=C1CC=C(C)C	3341.3	Standard non polar	33892256
Licorisoflavan A	COC1=CC2=C(CC(CO2)C2=C(O)C(CC=C(C)C)=C(O)C=C2)C(OC)=C1CC=C(C)C	3679.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Licorisoflavan A,1TMS,isomer #1	COC1=CC2=C(CC(C3=CC=C(O)C(CC=C(C)C)=C3O[Si](C)(C)C)CO2)C(OC)=C1CC=C(C)C	3408.5	Semi standard non polar	33892256
Licorisoflavan A,1TMS,isomer #2	COC1=CC2=C(CC(C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3O)CO2)C(OC)=C1CC=C(C)C	3428.8	Semi standard non polar	33892256
Licorisoflavan A,2TMS,isomer #1	COC1=CC2=C(CC(C3=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C3O[Si](C)(C)C)CO2)C(OC)=C1CC=C(C)C	3321.2	Semi standard non polar	33892256
Licorisoflavan A,1TBDMS,isomer #1	COC1=CC2=C(CC(C3=CC=C(O)C(CC=C(C)C)=C3O[Si](C)(C)C(C)(C)C)CO2)C(OC)=C1CC=C(C)C	3617.8	Semi standard non polar	33892256
Licorisoflavan A,1TBDMS,isomer #2	COC1=CC2=C(CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3O)CO2)C(OC)=C1CC=C(C)C	3657.3	Semi standard non polar	33892256
Licorisoflavan A,2TBDMS,isomer #1	COC1=CC2=C(CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C3O[Si](C)(C)C(C)(C)C)CO2)C(OC)=C1CC=C(C)C	3705.2	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 - Licorisoflavan A GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1109800000-4255f6cf9866ea4a7a97	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licorisoflavan A GC-MS (2 TMS) - 70eV, Positive	splash10-014i-1000090000-492f8dffb666696d33ac	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licorisoflavan 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 - Licorisoflavan A 10V, Positive-QTOF	splash10-000i-0093500000-f4335a61bdc7f39b4e47	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 20V, Positive-QTOF	splash10-00sr-1192200000-f863067be062a97637ed	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 40V, Positive-QTOF	splash10-0gbi-4591200000-e6f5bbf39fbb769d0fc8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 10V, Negative-QTOF	splash10-000i-0040900000-86615ab5d06d504765a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 20V, Negative-QTOF	splash10-004r-0492600000-46200ec06f9bb5a7327a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 40V, Negative-QTOF	splash10-0v00-0492100000-0c4dca00a8b03f63a925	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 10V, Negative-QTOF	splash10-000i-0000900000-af1cbe7862813d35c379	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 20V, Negative-QTOF	splash10-052r-0005900000-7b4e840ba957fa41e12a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 40V, Negative-QTOF	splash10-0a4i-0539800000-201b4f0b6bbc6a370395	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 10V, Positive-QTOF	splash10-001i-0009200000-6c19781b4b36934113bf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 20V, Positive-QTOF	splash10-0059-0009000000-a4b1b6e79e2034416f0b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licorisoflavan A 40V, Positive-QTOF	splash10-002f-2529000000-d7e096d7f4cf806ee12b	2021-09-24	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

FDB012477

KNApSAcK ID

C00010036

Chemspider ID

4477945

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319704

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1841001

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 Licorisoflavan A (HMDB0034184)

MOL for HMDB0034184 (Licorisoflavan A)

3D MOL for HMDB0034184 (Licorisoflavan A)

3D SDF for HMDB0034184 (Licorisoflavan A)

3D-SDF for HMDB0034184 (Licorisoflavan A)

PDB for HMDB0034184 (Licorisoflavan A)

3D PDB for HMDB0034184 (Licorisoflavan A)

SMILES for HMDB0034184 (Licorisoflavan A)

INCHI for HMDB0034184 (Licorisoflavan A)

Structure for HMDB0034184 (Licorisoflavan A)

3D Structure for HMDB0034184 (Licorisoflavan A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra