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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:19 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030834

Secondary Accession Numbers

HMDB30834

Metabolite Identification

Common Name

Americanin A

Description

Americanin A 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 A has been detected, but not quantified in, a few different foods, such as american pokeweeds (Phytolacca americana), fruits, and green vegetables. This could make americanin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Americanin A.

Structure

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

HMDB0030834
     RDKit          3D
Americanin A
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.9023    2.2691    1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379    1.7634    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5134    1.4299   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4089    0.9530   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065    0.6815   -0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7411    1.2717    0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.8214    1.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.2257    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359   -0.8334   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -0.4164   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986   -1.9057   -0.6549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7757   -2.0182   -0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -3.4924   -0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819   -4.1322   -1.5283 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -1.2758    0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2398   -0.2015    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405    1.0471   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7339    2.0420   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    1.8075   -0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0450    2.7731   -0.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5220    0.5593    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950    0.3391    0.2425 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144   -0.4165    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2550   -0.7350    1.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0694    1.6378    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3708    1.5922   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4014    0.7414   -2.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2395    2.1691    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841    1.3187    2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089   -0.8853   -1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944   -1.6372   -1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -3.5296   -0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797   -3.9977    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954   -3.5627   -2.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427   -1.9858    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952    1.2775   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4313    3.0226   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944    3.6702   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -0.5487    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -1.3875    0.8192 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  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 15 24  1  0
 10  5  1  0
 23 16  1  0
 24  8  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 22 39  1  0
 23 40  1  0
M  END


  Mrv0541 05061305322D          

 24 26  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
    4.2868    0.0000    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
   -2.1434   -0.4125    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
    2.8579    0.8250    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
   -0.7145   -1.2375    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
    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
    0.7145   -0.4125    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   -0.4125    0.0000 C   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
    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
  2  1  2  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
  7  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  8  2  0  0  0  0
 12  4  1  0  0  0  0
 12  9  2  0  0  0  0
 13  5  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  2  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19  7  2  0  0  0  0
 20 10  1  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24 15  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030834

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC2=C(OC1C1=CC(O)=C(O)C=C1)C=CC(\C=C/C=O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)23-17(10-20)18(24-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1-

> <INCHI_KEY>
NTXXGPYGMQQSML-UPHRSURJSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.316

> <EXACT_MASS>
328.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
32.91588922461648

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.037377135

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.653886056944042

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207264273796575

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904143046329557

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
87.299

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.36e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030834
     RDKit          3D
Americanin A
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.9023    2.2691    1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379    1.7634    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5134    1.4299   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4089    0.9530   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065    0.6815   -0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7411    1.2717    0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.8214    1.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.2257    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359   -0.8334   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -0.4164   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986   -1.9057   -0.6549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7757   -2.0182   -0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -3.4924   -0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819   -4.1322   -1.5283 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -1.2758    0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2398   -0.2015    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405    1.0471   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7339    2.0420   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    1.8075   -0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0450    2.7731   -0.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5220    0.5593    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950    0.3391    0.2425 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144   -0.4165    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2550   -0.7350    1.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0694    1.6378    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3708    1.5922   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4014    0.7414   -2.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2395    2.1691    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841    1.3187    2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089   -0.8853   -1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944   -1.6372   -1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -3.5296   -0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797   -3.9977    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954   -3.5627   -2.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427   -1.9858    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952    1.2775   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4313    3.0226   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944    3.6702   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -0.5487    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -1.3875    0.8192 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  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 15 24  1  0
 10  5  1  0
 23 16  1  0
 24  8  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 22 39  1  0
 23 40  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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1   11                                                       
CONECT    3    6   11                                                       
CONECT    4    5   12                                                       
CONECT    5    4   13                                                       
CONECT    6    3   15                                                       
CONECT    7    1   19                                                       
CONECT    8   11   16                                                       
CONECT    9   12   14                                                       
CONECT   10   17   20                                                       
CONECT   11    2    3    8                                                  
CONECT   12    4    9   18                                                  
CONECT   13    5   14   21                                                  
CONECT   14    9   13   22                                                  
CONECT   15    6   16   24                                                  
CONECT   16    8   15   23                                                  
CONECT   17   10   18   23                                                  
CONECT   18   12   17   24                                                  
CONECT   19    7                                                            
CONECT   20   10                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23   16   17                                                       
CONECT   24   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0030834
HETATM    1  O1  UNL     1      -6.902   2.269   1.062  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.738   1.763   0.808  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.513   1.430  -0.559  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.409   0.953  -1.043  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.206   0.682  -0.338  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.741   1.272   0.812  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.605   0.821   1.458  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.894  -0.226   0.981  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.336  -0.833  -0.172  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.455  -0.416  -0.836  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.599  -1.906  -0.655  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.776  -2.018  -0.434  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.123  -3.492  -0.343  1.00  0.00           C  
HETATM   14  O3  UNL     1       0.782  -4.132  -1.528  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.273  -1.276   0.769  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.240  -0.202   0.408  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.841   1.047  -0.017  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.734   2.042  -0.351  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.094   1.807  -0.265  1.00  0.00           C  
HETATM   20  O4  UNL     1       5.045   2.773  -0.588  1.00  0.00           O  
HETATM   21  C17 UNL     1       4.522   0.559   0.161  1.00  0.00           C  
HETATM   22  O5  UNL     1       5.895   0.339   0.242  1.00  0.00           O  
HETATM   23  C18 UNL     1       3.614  -0.417   0.488  1.00  0.00           C  
HETATM   24  O6  UNL     1       0.255  -0.735   1.572  1.00  0.00           O  
HETATM   25  H1  UNL     1      -5.069   1.638   1.616  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.371   1.592  -1.295  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.401   0.741  -2.155  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.239   2.169   1.190  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.284   1.319   2.360  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.809  -0.885  -1.737  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.294  -1.637  -1.345  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.233  -3.530  -0.176  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.580  -3.998   0.482  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.295  -3.563  -2.157  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.843  -1.986   1.437  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.795   1.278  -0.101  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.431   3.023  -0.685  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.694   3.670  -0.894  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.275  -0.549   0.546  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.938  -1.388   0.819  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   25
CONECT    3    4    4   26
CONECT    4    5   27
CONECT    5    6    6   10
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   24
CONECT    9   10   10   11
CONECT   10   30
CONECT   11   12
CONECT   12   13   15   31
CONECT   13   14   32   33
CONECT   14   34
CONECT   15   16   24   35
CONECT   16   17   17   23
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   21
CONECT   20   38
CONECT   21   22   23   23
CONECT   22   39
CONECT   23   40
END

HMDB0030834
     RDKit          3D
Americanin A
 40 42  0  0  0  0  0  0  0  0999 V2000
   -6.9023    2.2691    1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379    1.7634    0.8078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5134    1.4299   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4089    0.9530   -1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2065    0.6815   -0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7411    1.2717    0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    0.8214    1.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -0.2257    0.9814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359   -0.8334   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4545   -0.4164   -0.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5986   -1.9057   -0.6549 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7757   -2.0182   -0.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235   -3.4924   -0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7819   -4.1322   -1.5283 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726   -1.2758    0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2398   -0.2015    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405    1.0471   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7339    2.0420   -0.3508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    1.8075   -0.2646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0450    2.7731   -0.5878 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5220    0.5593    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950    0.3391    0.2425 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144   -0.4165    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2550   -0.7350    1.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0694    1.6378    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3708    1.5922   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4014    0.7414   -2.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2395    2.1691    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841    1.3187    2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8089   -0.8853   -1.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2944   -1.6372   -1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2328   -3.5296   -0.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797   -3.9977    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2954   -3.5627   -2.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427   -1.9858    1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952    1.2775   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4313    3.0226   -0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944    3.6702   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -0.5487    0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9385   -1.3875    0.8192 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  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 15 24  1  0
 10  5  1  0
 23 16  1  0
 24  8  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 22 39  1  0
 23 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-[2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3-hydroxymethyl-1,4-benzodioxin-6-yl]-2-propenal, 9ci	HMDB
Americanin	HMDB
Americanin a	MeSH

Chemical Formula

C₁₈H₁₆O₆

Average Molecular Weight

328.316

Monoisotopic Molecular Weight

328.094688244

IUPAC Name

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

Traditional Name

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

CAS Registry Number

69506-79-2

SMILES

OCC1OC2=C(OC1C1=CC(O)=C(O)C=C1)C=CC(\C=C/C=O)=C2

InChI Identifier

InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)23-17(10-20)18(24-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1-

InChI Key

NTXXGPYGMQQSML-UPHRSURJSA-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

Cell membrane (HMDB: HMDB0030834)

Cellular substructure

Membrane (HMDB: HMDB0030834)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030834)

Source

Endogenous

Endogenous (HMDB: HMDB0030834)

Plant

Plant (HMDB: HMDB0030834)

Exogenous

Food

Food (HMDB: HMDB0030834)

Vegetable

Shoot vegetable

American pokeweed (FooDB: FOOD00437)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	246 - 247 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5447 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	0.044 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.04	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.3 m³·mol⁻¹	ChemAxon
Polarizability	32.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	174.681	30932474
DeepCCS	[M-H]-	172.323	30932474
DeepCCS	[M-2H]-	206.408	30932474
DeepCCS	[M+Na]+	181.635	30932474
AllCCS	[M+H]+	176.6	32859911
AllCCS	[M+H-H2O]+	173.5	32859911
AllCCS	[M+NH4]+	179.4	32859911
AllCCS	[M+Na]+	180.3	32859911
AllCCS	[M-H]-	177.7	32859911
AllCCS	[M+Na-2H]-	177.2	32859911
AllCCS	[M+HCOO]-	176.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Americanin A	OCC1OC2=C(OC1C1=CC(O)=C(O)C=C1)C=CC(\C=C/C=O)=C2	4368.7	Standard polar	33892256
Americanin A	OCC1OC2=C(OC1C1=CC(O)=C(O)C=C1)C=CC(\C=C/C=O)=C2	3177.8	Standard non polar	33892256
Americanin A	OCC1OC2=C(OC1C1=CC(O)=C(O)C=C1)C=CC(\C=C/C=O)=C2	3353.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Americanin A,1TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC(/C=C\C=O)=CC=C2OC1C1=CC=C(O)C(O)=C1	3251.2	Semi standard non polar	33892256
Americanin A,1TMS,isomer #2	C[Si](C)(C)OC1=CC(C2OC3=CC=C(/C=C\C=O)C=C3OC2CO)=CC=C1O	3264.8	Semi standard non polar	33892256
Americanin A,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC=C(/C=C\C=O)C=C3OC2CO)C=C1O	3288.8	Semi standard non polar	33892256
Americanin A,2TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC(/C=C\C=O)=CC=C2OC1C1=CC=C(O[Si](C)(C)C)C(O)=C1	3241.0	Semi standard non polar	33892256
Americanin A,2TMS,isomer #2	C[Si](C)(C)OCC1OC2=CC(/C=C\C=O)=CC=C2OC1C1=CC=C(O)C(O[Si](C)(C)C)=C1	3225.0	Semi standard non polar	33892256
Americanin A,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC=C(/C=C\C=O)C=C3OC2CO)C=C1O[Si](C)(C)C	3295.8	Semi standard non polar	33892256
Americanin A,3TMS,isomer #1	C[Si](C)(C)OCC1OC2=CC(/C=C\C=O)=CC=C2OC1C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3234.4	Semi standard non polar	33892256
Americanin A,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC(/C=C\C=O)=CC=C2OC1C1=CC=C(O)C(O)=C1	3549.7	Semi standard non polar	33892256
Americanin A,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(C2OC3=CC=C(/C=C\C=O)C=C3OC2CO)=CC=C1O	3567.4	Semi standard non polar	33892256
Americanin A,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC=C(/C=C\C=O)C=C3OC2CO)C=C1O	3591.1	Semi standard non polar	33892256
Americanin A,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC(/C=C\C=O)=CC=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	3783.2	Semi standard non polar	33892256
Americanin A,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC2=CC(/C=C\C=O)=CC=C2OC1C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	3755.9	Semi standard non polar	33892256
Americanin A,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC=C(/C=C\C=O)C=C3OC2CO)C=C1O[Si](C)(C)C(C)(C)C	3801.3	Semi standard non polar	33892256
Americanin A,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC2=CC(/C=C\C=O)=CC=C2OC1C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3938.1	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 A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2693000000-d6b7904621048fb0e12c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Americanin A GC-MS (3 TMS) - 70eV, Positive	splash10-0fir-6030590000-27ccf2d26454b0c6f6f7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Americanin 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 - Americanin A 10V, Positive-QTOF	splash10-01t9-0539000000-42454b3e0668e603e26c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 20V, Positive-QTOF	splash10-01p9-0593000000-d0de486e46c3376b4966	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 40V, Positive-QTOF	splash10-0ac0-2900000000-3a1c8b9e517fa46c1da4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 10V, Negative-QTOF	splash10-004i-0009000000-1e262c6723c00e3c6841	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 20V, Negative-QTOF	splash10-056s-1869000000-737a994f1dd60d810cec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 40V, Negative-QTOF	splash10-0002-2910000000-4836cc54f78b39b322b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 10V, Negative-QTOF	splash10-004i-0029000000-43efadddb5f47f86a896	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 20V, Negative-QTOF	splash10-00mk-0293000000-e4eb1c28f28d29a1c1c1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 40V, Negative-QTOF	splash10-00pi-1595000000-c17b21e368bf2b222a89	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 10V, Positive-QTOF	splash10-01t9-0019000000-3e811f26c46b0ba53c14	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 20V, Positive-QTOF	splash10-03fr-0389000000-42425774393c8d5ae69c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Americanin A 40V, Positive-QTOF	splash10-00di-0931000000-a0b06cf6398731b2605a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002790

KNApSAcK ID

C00031592

Chemspider ID

35013270

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751085

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1823091

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 A (HMDB0030834)

MOL for HMDB0030834 (Americanin A)

3D MOL for HMDB0030834 (Americanin A)

3D SDF for HMDB0030834 (Americanin A)

3D-SDF for HMDB0030834 (Americanin A)

PDB for HMDB0030834 (Americanin A)

3D PDB for HMDB0030834 (Americanin A)

SMILES for HMDB0030834 (Americanin A)

INCHI for HMDB0030834 (Americanin A)

Structure for HMDB0030834 (Americanin A)

3D Structure for HMDB0030834 (Americanin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra