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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:34:33 UTC

Update Date

2022-03-07 02:55:17 UTC

HMDB ID

HMDB0037338

Secondary Accession Numbers

HMDB37338

Metabolite Identification

Common Name

Americanin B

Description

Americanin B belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety. Americanin B has been detected, but not quantified in, fruits. This could make americanin b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Americanin B.

Structure

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


  Mrv0541 05061309432D          

 36 40  0  0  0  0            999 V2000
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  2  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15 10  2  0  0  0  0
 16  4  1  0  0  0  0
 16 11  2  0  0  0  0
 17  5  1  0  0  0  0
 17 12  2  0  0  0  0
 18  6  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  2  0  0  0  0
 20  7  1  0  0  0  0
 21  8  1  0  0  0  0
 22 10  1  0  0  0  0
 22 20  2  0  0  0  0
 23 12  1  0  0  0  0
 23 21  2  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26 16  1  0  0  0  0
 26 25  1  0  0  0  0
 27 17  1  0  0  0  0
 27 24  1  0  0  0  0
 28  9  2  0  0  0  0
 29 13  1  0  0  0  0
 30 14  1  0  0  0  0
 31 18  1  0  0  0  0
 32 19  1  0  0  0  0
 33 20  1  0  0  0  0
 33 24  1  0  0  0  0
 34 23  1  0  0  0  0
 34 25  1  0  0  0  0
 35 21  1  0  0  0  0
 35 26  1  0  0  0  0
 36 22  1  0  0  0  0
 36 27  1  0  0  0  0
M  END

HMDB0037338
     RDKit          3D
Americanin B
 60 64  0  0  0  0  0  0  0  0999 V2000
    9.3795   -0.4660    4.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8505   -0.4099    2.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9213   -0.3294    1.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6172   -0.3163    2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -0.2371    0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0410   -0.1704   -0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748   -0.0978   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298   -0.0876   -1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.1541    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3084   -0.2270    1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -0.1429    0.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    0.5826   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6920    0.1165   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633   -1.2225   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -1.6420    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720   -0.7446    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596    0.6031    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.0143   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931    1.4942    0.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0638    1.1982    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5701    1.9690   -1.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4534    3.3279   -1.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.2427   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6019   -0.7679    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710   -2.1434    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9185   -2.7566    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9524   -1.9782    1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1555   -2.5523    1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7767   -0.6020    1.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8266    0.1984    1.6535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6178    0.0259    0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3102   -1.0825    0.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574    0.5208   -1.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343    1.9385   -2.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    1.8829   -3.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392   -0.0160   -2.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9076   -0.4205    2.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3621   -0.2828    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3011   -0.3678    3.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0789   -0.1737   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3568   -0.0440   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -0.2785    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.6410    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1577   -1.9487   -0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -2.6959    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100    2.0668   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5928    1.6312    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451    1.5891   -2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6374    1.7102   -1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9649    3.5572   -0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -0.4690   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9685   -2.7973   -0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0605   -3.8311    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2163   -3.5588    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7681    1.1861    1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313    1.1135    0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -0.0820   -2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309    2.3886   -2.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2540    2.4871   -1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2432    1.0961   -3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 23 32  1  0
 12 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 10  5  1  0
 18 13  1  0
 31 24  1  0
 36  8  1  0
 32 16  1  0
  2 37  1  0
  3 38  1  0
  4 39  1  0
  6 40  1  0
  7 41  1  0
 10 42  1  0
 12 43  1  0
 14 44  1  0
 15 45  1  0
 18 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 25 52  1  0
 26 53  1  0
 28 54  1  0
 30 55  1  0
 31 56  1  0
 33 57  1  0
 34 58  1  0
 34 59  1  0
 35 60  1  0
M  END


  Mrv0541 05061309432D          

 36 40  0  0  0  0            999 V2000
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  4  2  0  0  0  0
  7  3  2  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15 10  2  0  0  0  0
 16  4  1  0  0  0  0
 16 11  2  0  0  0  0
 17  5  1  0  0  0  0
 17 12  2  0  0  0  0
 18  6  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  2  0  0  0  0
 20  7  1  0  0  0  0
 21  8  1  0  0  0  0
 22 10  1  0  0  0  0
 22 20  2  0  0  0  0
 23 12  1  0  0  0  0
 23 21  2  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
 26 16  1  0  0  0  0
 26 25  1  0  0  0  0
 27 17  1  0  0  0  0
 27 24  1  0  0  0  0
 28  9  2  0  0  0  0
 29 13  1  0  0  0  0
 30 14  1  0  0  0  0
 31 18  1  0  0  0  0
 32 19  1  0  0  0  0
 33 20  1  0  0  0  0
 33 24  1  0  0  0  0
 34 23  1  0  0  0  0
 34 25  1  0  0  0  0
 35 21  1  0  0  0  0
 35 26  1  0  0  0  0
 36 22  1  0  0  0  0
 36 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037338

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC2=C(OC1C1=CC3=C(OC(C(CO)O3)C3=CC(O)=C(O)C=C3)C=C1)C=C(\C=C\C=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O9/c28-9-1-2-15-3-7-20-22(10-15)36-27(24(13-29)33-20)17-5-8-21-23(12-17)34-25(14-30)26(35-21)16-4-6-18(31)19(32)11-16/h1-12,24-27,29-32H,13-14H2/b2-1+

> <INCHI_KEY>
VDIFGESBHJLSFS-OWOJBTEDSA-N

> <FORMULA>
C27H24O9

> <MOLECULAR_WEIGHT>
492.4741

> <EXACT_MASS>
492.142032366

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
50.51174933749414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-{3-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl}prop-2-enal

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.704414905666666

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.64855370175884

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207262354625946

> <JCHEM_PKA_STRONGEST_BASIC>
-2.990414063819836

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
128.50169999999991

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-{3-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl}prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037338
     RDKit          3D
Americanin B
 60 64  0  0  0  0  0  0  0  0999 V2000
    9.3795   -0.4660    4.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8505   -0.4099    2.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9213   -0.3294    1.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6172   -0.3163    2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -0.2371    0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0410   -0.1704   -0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748   -0.0978   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298   -0.0876   -1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.1541    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3084   -0.2270    1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -0.1429    0.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    0.5826   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6920    0.1165   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633   -1.2225   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -1.6420    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720   -0.7446    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596    0.6031    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.0143   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931    1.4942    0.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0638    1.1982    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5701    1.9690   -1.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4534    3.3279   -1.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.2427   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6019   -0.7679    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710   -2.1434    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9185   -2.7566    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9524   -1.9782    1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1555   -2.5523    1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7767   -0.6020    1.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8266    0.1984    1.6535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6178    0.0259    0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3102   -1.0825    0.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574    0.5208   -1.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343    1.9385   -2.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    1.8829   -3.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392   -0.0160   -2.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9076   -0.4205    2.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3621   -0.2828    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3011   -0.3678    3.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0789   -0.1737   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3568   -0.0440   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -0.2785    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.6410    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1577   -1.9487   -0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -2.6959    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100    2.0668   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5928    1.6312    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451    1.5891   -2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6374    1.7102   -1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9649    3.5572   -0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -0.4690   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9685   -2.7973   -0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0605   -3.8311    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2163   -3.5588    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7681    1.1861    1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313    1.1135    0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -0.0820   -2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309    2.3886   -2.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2540    2.4871   -1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2432    1.0961   -3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 23 32  1  0
 12 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 10  5  1  0
 18 13  1  0
 31 24  1  0
 36  8  1  0
 32 16  1  0
  2 37  1  0
  3 38  1  0
  4 39  1  0
  6 40  1  0
  7 41  1  0
 10 42  1  0
 12 43  1  0
 14 44  1  0
 15 45  1  0
 18 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 25 52  1  0
 26 53  1  0
 28 54  1  0
 30 55  1  0
 31 56  1  0
 33 57  1  0
 34 58  1  0
 34 59  1  0
 35 60  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      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   2.310   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -2.310   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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   15                                                       
CONECT    3    7   15                                                       
CONECT    4    6   16                                                       
CONECT    5    8   17                                                       
CONECT    6    4   18                                                       
CONECT    7    3   20                                                       
CONECT    8    5   21                                                       
CONECT    9    1   28                                                       
CONECT   10   15   22                                                       
CONECT   11   16   19                                                       
CONECT   12   17   23                                                       
CONECT   13   24   29                                                       
CONECT   14   25   30                                                       
CONECT   15    2    3   10                                                  
CONECT   16    4   11   26                                                  
CONECT   17    5   12   27                                                  
CONECT   18    6   19   31                                                  
CONECT   19   11   18   32                                                  
CONECT   20    7   22   33                                                  
CONECT   21    8   23   35                                                  
CONECT   22   10   20   36                                                  
CONECT   23   12   21   34                                                  
CONECT   24   13   27   33                                                  
CONECT   25   14   26   34                                                  
CONECT   26   16   25   35                                                  
CONECT   27   17   24   36                                                  
CONECT   28    9                                                            
CONECT   29   13                                                            
CONECT   30   14                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   20   24                                                       
CONECT   34   23   25                                                       
CONECT   35   21   26                                                       
CONECT   36   22   27                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0037338
HETATM    1  O1  UNL     1       9.379  -0.466   4.153  1.00  0.00           O  
HETATM    2  C1  UNL     1       9.850  -0.410   2.984  1.00  0.00           C  
HETATM    3  C2  UNL     1       8.921  -0.329   1.849  1.00  0.00           C  
HETATM    4  C3  UNL     1       7.617  -0.316   2.053  1.00  0.00           C  
HETATM    5  C4  UNL     1       6.679  -0.237   0.946  1.00  0.00           C  
HETATM    6  C5  UNL     1       7.041  -0.170  -0.375  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.075  -0.098  -1.356  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.730  -0.088  -1.086  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.351  -0.154   0.238  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.308  -0.227   1.227  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.990  -0.143   0.495  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.082   0.583  -0.349  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.692   0.116  -0.164  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.363  -1.222  -0.107  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.954  -1.642   0.068  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.972  -0.745   0.192  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.660   0.603   0.137  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.349   1.014  -0.037  1.00  0.00           C  
HETATM   19  O3  UNL     1      -2.693   1.494   0.263  1.00  0.00           O  
HETATM   20  C17 UNL     1      -4.064   1.198   0.045  1.00  0.00           C  
HETATM   21  C18 UNL     1      -4.570   1.969  -1.181  1.00  0.00           C  
HETATM   22  O4  UNL     1      -4.453   3.328  -1.027  1.00  0.00           O  
HETATM   23  C19 UNL     1      -4.323  -0.243  -0.193  1.00  0.00           C  
HETATM   24  C20 UNL     1      -5.602  -0.768   0.279  1.00  0.00           C  
HETATM   25  C21 UNL     1      -5.771  -2.143   0.235  1.00  0.00           C  
HETATM   26  C22 UNL     1      -6.918  -2.757   0.646  1.00  0.00           C  
HETATM   27  C23 UNL     1      -7.952  -1.978   1.125  1.00  0.00           C  
HETATM   28  O5  UNL     1      -9.156  -2.552   1.561  1.00  0.00           O  
HETATM   29  C24 UNL     1      -7.777  -0.602   1.166  1.00  0.00           C  
HETATM   30  O6  UNL     1      -8.827   0.198   1.653  1.00  0.00           O  
HETATM   31  C25 UNL     1      -6.618   0.026   0.752  1.00  0.00           C  
HETATM   32  O7  UNL     1      -3.310  -1.082   0.369  1.00  0.00           O  
HETATM   33  C26 UNL     1       2.457   0.521  -1.790  1.00  0.00           C  
HETATM   34  C27 UNL     1       2.434   1.939  -2.342  1.00  0.00           C  
HETATM   35  O8  UNL     1       2.687   1.883  -3.703  1.00  0.00           O  
HETATM   36  O9  UNL     1       3.739  -0.016  -2.042  1.00  0.00           O  
HETATM   37  H1  UNL     1      10.908  -0.421   2.819  1.00  0.00           H  
HETATM   38  H2  UNL     1       9.362  -0.283   0.864  1.00  0.00           H  
HETATM   39  H3  UNL     1       7.301  -0.368   3.086  1.00  0.00           H  
HETATM   40  H4  UNL     1       8.079  -0.174  -0.665  1.00  0.00           H  
HETATM   41  H5  UNL     1       6.357  -0.044  -2.419  1.00  0.00           H  
HETATM   42  H6  UNL     1       4.992  -0.278   2.259  1.00  0.00           H  
HETATM   43  H7  UNL     1       2.135   1.641   0.040  1.00  0.00           H  
HETATM   44  H8  UNL     1       1.158  -1.949  -0.203  1.00  0.00           H  
HETATM   45  H9  UNL     1      -1.181  -2.696   0.109  1.00  0.00           H  
HETATM   46  H10 UNL     1      -0.110   2.067  -0.079  1.00  0.00           H  
HETATM   47  H11 UNL     1      -4.593   1.631   0.915  1.00  0.00           H  
HETATM   48  H12 UNL     1      -4.045   1.589  -2.085  1.00  0.00           H  
HETATM   49  H13 UNL     1      -5.637   1.710  -1.327  1.00  0.00           H  
HETATM   50  H14 UNL     1      -3.965   3.557  -0.203  1.00  0.00           H  
HETATM   51  H15 UNL     1      -4.278  -0.469  -1.300  1.00  0.00           H  
HETATM   52  H16 UNL     1      -4.969  -2.797  -0.141  1.00  0.00           H  
HETATM   53  H17 UNL     1      -7.060  -3.831   0.615  1.00  0.00           H  
HETATM   54  H18 UNL     1      -9.216  -3.559   1.503  1.00  0.00           H  
HETATM   55  H19 UNL     1      -8.768   1.186   1.711  1.00  0.00           H  
HETATM   56  H20 UNL     1      -6.531   1.114   0.806  1.00  0.00           H  
HETATM   57  H21 UNL     1       1.706  -0.082  -2.378  1.00  0.00           H  
HETATM   58  H22 UNL     1       1.431   2.389  -2.125  1.00  0.00           H  
HETATM   59  H23 UNL     1       3.254   2.487  -1.843  1.00  0.00           H  
HETATM   60  H24 UNL     1       3.243   1.096  -3.925  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   37
CONECT    3    4    4   38
CONECT    4    5   39
CONECT    5    6    6   10
CONECT    6    7   40
CONECT    7    8    8   41
CONECT    8    9   36
CONECT    9   10   10   11
CONECT   10   42
CONECT   11   12
CONECT   12   13   33   43
CONECT   13   14   14   18
CONECT   14   15   44
CONECT   15   16   16   45
CONECT   16   17   32
CONECT   17   18   18   19
CONECT   18   46
CONECT   19   20
CONECT   20   21   23   47
CONECT   21   22   48   49
CONECT   22   50
CONECT   23   24   32   51
CONECT   24   25   25   31
CONECT   25   26   52
CONECT   26   27   27   53
CONECT   27   28   29
CONECT   28   54
CONECT   29   30   31   31
CONECT   30   55
CONECT   31   56
CONECT   33   34   36   57
CONECT   34   35   58   59
CONECT   35   60
END

HMDB0037338
     RDKit          3D
Americanin B
 60 64  0  0  0  0  0  0  0  0999 V2000
    9.3795   -0.4660    4.1527 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8505   -0.4099    2.9836 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9213   -0.3294    1.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6172   -0.3163    2.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -0.2371    0.9462 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0410   -0.1704   -0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748   -0.0978   -1.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298   -0.0876   -1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3506   -0.1541    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3084   -0.2270    1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9899   -0.1429    0.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    0.5826   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6920    0.1165   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633   -1.2225   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -1.6420    0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720   -0.7446    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6596    0.6031    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.0143   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6931    1.4942    0.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0638    1.1982    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5701    1.9690   -1.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4534    3.3279   -1.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3233   -0.2427   -0.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6019   -0.7679    0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7710   -2.1434    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9185   -2.7566    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9524   -1.9782    1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1555   -2.5523    1.5608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7767   -0.6020    1.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8266    0.1984    1.6535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6178    0.0259    0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3102   -1.0825    0.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574    0.5208   -1.7898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343    1.9385   -2.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6868    1.8829   -3.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7392   -0.0160   -2.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9076   -0.4205    2.8193 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3621   -0.2828    0.8645 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3011   -0.3678    3.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0789   -0.1737   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3568   -0.0440   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9924   -0.2785    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.6410    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1577   -1.9487   -0.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -2.6959    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1100    2.0668   -0.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5928    1.6312    0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451    1.5891   -2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6374    1.7102   -1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9649    3.5572   -0.2027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2779   -0.4690   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9685   -2.7973   -0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0605   -3.8311    0.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2163   -3.5588    1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7681    1.1861    1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5313    1.1135    0.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -0.0820   -2.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309    2.3886   -2.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2540    2.4871   -1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2432    1.0961   -3.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 23 32  1  0
 12 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 10  5  1  0
 18 13  1  0
 31 24  1  0
 36  8  1  0
 32 16  1  0
  2 37  1  0
  3 38  1  0
  4 39  1  0
  6 40  1  0
  7 41  1  0
 10 42  1  0
 12 43  1  0
 14 44  1  0
 15 45  1  0
 18 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 25 52  1  0
 26 53  1  0
 28 54  1  0
 30 55  1  0
 31 56  1  0
 33 57  1  0
 34 58  1  0
 34 59  1  0
 35 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Americanin b	MeSH

Chemical Formula

C₂₇H₂₄O₉

Average Molecular Weight

492.4741

Monoisotopic Molecular Weight

492.142032366

IUPAC Name

(2E)-3-{3-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl}prop-2-enal

Traditional Name

(2E)-3-{3-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl}prop-2-enal

CAS Registry Number

77053-44-2

SMILES

OCC1OC2=C(OC1C1=CC3=C(OC(C(CO)O3)C3=CC(O)=C(O)C=C3)C=C1)C=C(\C=C\C=O)C=C2

InChI Identifier

InChI=1S/C27H24O9/c28-9-1-2-15-3-7-20-22(10-15)36-27(24(13-29)33-20)17-5-8-21-23(12-17)34-25(14-30)26(35-21)16-4-6-18(31)19(32)11-16/h1-12,24-27,29-32H,13-14H2/b2-1+

InChI Key

VDIFGESBHJLSFS-OWOJBTEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzo-1,4-dioxanes. These are benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxanes

Sub Class

Phenylbenzodioxanes

Direct Parent

Phenylbenzo-1,4-dioxanes

Alternative Parents

Substituents

2-phenylbenzo-1,4-dioxane
Benzo-1,4-dioxane
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Para-dioxin
Benzenoid
Enal
Alpha,beta-unsaturated aldehyde
Ether
Oxacycle
Aldehyde
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Organic oxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0037338)
Cell membrane (HMDB: HMDB0037338)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037338)

Source

Exogenous

Exogenous (HMDB: HMDB0037338)

Food

Food (HMDB: HMDB0037338)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0037338)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037338)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	258 - 260 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	20.73 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	0.021 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.7	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.5 m³·mol⁻¹	ChemAxon
Polarizability	50.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M+H]+	210.294	30932474
DeepCCS	[M-H]-	207.898	30932474
DeepCCS	[M-2H]-	240.781	30932474
DeepCCS	[M+Na]+	216.304	30932474
AllCCS	[M+H]+	214.1	32859911
AllCCS	[M+H-H2O]+	212.3	32859911
AllCCS	[M+NH4]+	215.6	32859911
AllCCS	[M+Na]+	216.1	32859911
AllCCS	[M-H]-	207.0	32859911
AllCCS	[M+Na-2H]-	207.4	32859911
AllCCS	[M+HCOO]-	207.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.85 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2658 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.63 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2419.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	197.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	120.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	594.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	493.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	143.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1046.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	506.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1460.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	283.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	127.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Americanin B	OCC1OC2=C(OC1C1=CC3=C(OC(C(CO)O3)C3=CC(O)=C(O)C=C3)C=C1)C=C(\C=C\C=O)C=C2	5775.0	Standard polar	33892256
Americanin B	OCC1OC2=C(OC1C1=CC3=C(OC(C(CO)O3)C3=CC(O)=C(O)C=C3)C=C1)C=C(\C=C\C=O)C=C2	4486.5	Standard non polar	33892256
Americanin B	OCC1OC2=C(OC1C1=CC3=C(OC(C(CO)O3)C3=CC(O)=C(O)C=C3)C=C1)C=C(\C=C\C=O)C=C2	4826.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Americanin B,1TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC=C(/C=C/C=O)C=C2OC1C1=CC=C2OC(C3=CC=C(O)C(O)=C3)C(CO)OC2=C1	4756.2	Semi standard non polar	33892256
Americanin B,1TMS,isomer #2	C[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO)=CC=C2OC1C1=CC=C(O)C(O)=C1	4762.4	Semi standard non polar	33892256
Americanin B,1TMS,isomer #3	C[Si](C)(C)OC1=CC(C2OC3=CC=C(C4OC5=CC(/C=C/C=O)=CC=C5OC4CO)C=C3OC2CO)=CC=C1O	4785.5	Semi standard non polar	33892256
Americanin B,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2OC3=CC=C(C4OC5=CC(/C=C/C=O)=CC=C5OC4CO)C=C3OC2CO)C=C1O	4798.7	Semi standard non polar	33892256
Americanin B,2TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO[Si](C)(C)C)=CC=C2OC1C1=CC=C(O)C(O)=C1	4564.5	Semi standard non polar	33892256
Americanin B,2TMS,isomer #2	C[Si](C)(C)OCC1OC2=CC=C(/C=C/C=O)C=C2OC1C1=CC=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)C(CO)OC2=C1	4685.6	Semi standard non polar	33892256
Americanin B,2TMS,isomer #3	C[Si](C)(C)OCC1OC2=CC=C(/C=C/C=O)C=C2OC1C1=CC=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)C(CO)OC2=C1	4671.6	Semi standard non polar	33892256
Americanin B,2TMS,isomer #4	C[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO)=CC=C2OC1C1=CC=C(O[Si](C)(C)C)C(O)=C1	4692.0	Semi standard non polar	33892256
Americanin B,2TMS,isomer #5	C[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO)=CC=C2OC1C1=CC=C(O)C(O[Si](C)(C)C)=C1	4679.1	Semi standard non polar	33892256
Americanin B,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C2OC3=CC=C(C4OC5=CC(/C=C/C=O)=CC=C5OC4CO)C=C3OC2CO)C=C1O[Si](C)(C)C	4769.0	Semi standard non polar	33892256
Americanin B,3TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO[Si](C)(C)C)=CC=C2OC1C1=CC=C(O[Si](C)(C)C)C(O)=C1	4496.2	Semi standard non polar	33892256
Americanin B,3TMS,isomer #2	C[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO[Si](C)(C)C)=CC=C2OC1C1=CC=C(O)C(O[Si](C)(C)C)=C1	4498.3	Semi standard non polar	33892256
Americanin B,3TMS,isomer #3	C[Si](C)(C)OCC1OC2=CC=C(/C=C/C=O)C=C2OC1C1=CC=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)C(CO)OC2=C1	4598.2	Semi standard non polar	33892256
Americanin B,3TMS,isomer #4	C[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO)=CC=C2OC1C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	4610.6	Semi standard non polar	33892256
Americanin B,4TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO[Si](C)(C)C)=CC=C2OC1C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	4447.9	Semi standard non polar	33892256
Americanin B,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC=C(/C=C/C=O)C=C2OC1C1=CC=C2OC(C3=CC=C(O)C(O)=C3)C(CO)OC2=C1	5028.6	Semi standard non polar	33892256
Americanin B,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO)=CC=C2OC1C1=CC=C(O)C(O)=C1	5033.4	Semi standard non polar	33892256
Americanin B,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(C2OC3=CC=C(C4OC5=CC(/C=C/C=O)=CC=C5OC4CO)C=C3OC2CO)=CC=C1O	5057.0	Semi standard non polar	33892256
Americanin B,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC=C(C4OC5=CC(/C=C/C=O)=CC=C5OC4CO)C=C3OC2CO)C=C1O	5069.1	Semi standard non polar	33892256
Americanin B,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO[Si](C)(C)C(C)(C)C)=CC=C2OC1C1=CC=C(O)C(O)=C1	5082.9	Semi standard non polar	33892256
Americanin B,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC2=CC=C(/C=C/C=O)C=C2OC1C1=CC=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)C(CO)OC2=C1	5191.0	Semi standard non polar	33892256
Americanin B,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1OC2=CC=C(/C=C/C=O)C=C2OC1C1=CC=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)C(CO)OC2=C1	5168.4	Semi standard non polar	33892256
Americanin B,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO)=CC=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	5195.7	Semi standard non polar	33892256
Americanin B,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO)=CC=C2OC1C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	5174.1	Semi standard non polar	33892256
Americanin B,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC=C(C4OC5=CC(/C=C/C=O)=CC=C5OC4CO)C=C3OC2CO)C=C1O[Si](C)(C)C(C)(C)C	5240.8	Semi standard non polar	33892256
Americanin B,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO[Si](C)(C)C(C)(C)C)=CC=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	5199.5	Semi standard non polar	33892256
Americanin B,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO[Si](C)(C)C(C)(C)C)=CC=C2OC1C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	5187.3	Semi standard non polar	33892256
Americanin B,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1OC2=CC=C(/C=C/C=O)C=C2OC1C1=CC=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)C(CO)OC2=C1	5270.4	Semi standard non polar	33892256
Americanin B,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC1OC2=CC(C3OC4=CC(/C=C/C=O)=CC=C4OC3CO)=CC=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	5269.0	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 - Americanin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0210900000-beca3e99c3d206d4bdd9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Americanin B GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6200049000-29d3e45ed245967481a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Americanin B 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 - Americanin B 10V, Positive-QTOF	splash10-002f-0312900000-64475446763fa1c909de	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 20V, Positive-QTOF	splash10-002b-0210900000-745e78b9e00aea8746f3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 40V, Positive-QTOF	splash10-000t-0910000000-359177e9fdd57650c3ea	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 10V, Negative-QTOF	splash10-0006-0000900000-a4492fbdd249415c899b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 20V, Negative-QTOF	splash10-0096-0402900000-dbd90a9592280f063f28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 40V, Negative-QTOF	splash10-00kb-1920200000-21bd31af98517a0dbd56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 10V, Negative-QTOF	splash10-0006-0001900000-98c0719f6022e9bd138a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 20V, Negative-QTOF	splash10-001i-0112900000-21cee2262248e02e822a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 40V, Negative-QTOF	splash10-0019-0322900000-ad6c912b7edd52020b98	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 10V, Positive-QTOF	splash10-0006-0003900000-5de809821d9f6bbc4708	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 20V, Positive-QTOF	splash10-0037-0002900000-c1264c0170936e1c941f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin B 40V, Positive-QTOF	splash10-009f-0625900000-e560d70ff502cb64ad9f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016360

KNApSAcK ID

C00055486

Chemspider ID

30839456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73352644

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859971

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 Americanin B (HMDB0037338)

MOL for HMDB0037338 (Americanin B)

3D MOL for HMDB0037338 (Americanin B)

3D SDF for HMDB0037338 (Americanin B)

3D-SDF for HMDB0037338 (Americanin B)

PDB for HMDB0037338 (Americanin B)

3D PDB for HMDB0037338 (Americanin B)

SMILES for HMDB0037338 (Americanin B)

INCHI for HMDB0037338 (Americanin B)

Structure for HMDB0037338 (Americanin B)

3D Structure for HMDB0037338 (Americanin B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra