NP-MRD: Showing NP-Card for isoamericanol A (NP0030681)

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Record Information

Version

2.0

Created at

2021-06-19 21:58:16 UTC

Updated at

2021-06-29 23:58:48 UTC

NP-MRD ID

NP0030681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isoamericanol A

Provided By

JEOL Database JEOL Logo

Description

Isoamericanol 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. isoamericanol A is found in Capparis flavicans, Joannesia princeps and Phytolocca americana. isoamericanol A was first documented in 2003 (PMID: 12620334). Based on a literature review a small amount of articles have been published on Isoamericanol A (PMID: 24870973) (PMID: 20359228) (PMID: 15618635) (PMID: 27441238).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123583D          

 42 44  0  0  0  0            999 V2000
    1.9247   -5.6605   -0.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -5.2934    1.0845 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1767   -3.8603    1.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010   -2.8994    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.4883    1.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690   -0.7469    2.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318    0.6067    2.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    1.2343    2.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4350    0.5048    1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778   -0.8436    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    1.0470    0.9292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405    2.3117    1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1165    2.9269    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    3.0980   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079    3.6833   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    4.1000   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975    4.6802   -1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    3.9335    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4682    4.3471    0.9905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    3.3515    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2123    3.1939    1.6661 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9048    4.5665    2.2738 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1055    5.3370    2.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636    2.5651    2.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -5.0193   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724   -5.9277    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   -5.4813    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -3.6317    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -3.1494    1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5453   -1.2183    3.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1201    1.1692    3.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9869   -1.3814    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    2.0883    2.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0053    2.7630   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    3.7992   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    4.7179   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    4.7104    0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    3.2337    2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256    3.3298    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038    5.1393    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    4.4681    3.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587    4.7637    2.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  9  2  0  0  0  0
  3  2  1  0  0  0  0
 12 21  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 11  9  1  0  0  0  0
 10  5  2  0  0  0  0
 18 16  2  0  0  0  0
  8 24  1  0  0  0  0
 16 15  1  0  0  0  0
  5  6  1  0  0  0  0
 15 14  2  0  0  0  0
 14 13  1  0  0  0  0
 24 21  1  0  0  0  0
 13 20  2  0  0  0  0
 20 18  1  0  0  0  0
  6  7  2  0  0  0  0
 21 22  1  0  0  0  0
  7  8  1  0  0  0  0
 22 23  1  0  0  0  0
 12 11  1  0  0  0  0
 18 19  1  0  0  0  0
  5  4  1  0  0  0  0
 16 17  1  0  0  0  0
 12 33  1  1  0  0  0
 21 39  1  6  0  0  0
 10 32  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  0  0  0  0
  4 29  1  0  0  0  0
  3 28  1  0  0  0  0
  2 26  1  0  0  0  0
  2 27  1  0  0  0  0
  1 25  1  0  0  0  0
 15 35  1  0  0  0  0
 14 34  1  0  0  0  0
 20 38  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
 23 42  1  0  0  0  0
 19 37  1  0  0  0  0
 17 36  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    1.9247   -5.6605   -0.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -5.2934    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -3.8603    1.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010   -2.8994    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.4883    1.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690   -0.7469    2.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318    0.6067    2.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    1.2343    2.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4350    0.5048    1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778   -0.8436    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    1.0470    0.9292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405    2.3117    1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1165    2.9269    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    3.0980   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079    3.6833   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    4.1000   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975    4.6802   -1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    3.9335    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4682    4.3471    0.9905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    3.3515    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2123    3.1939    1.6661 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9048    4.5665    2.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055    5.3370    2.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636    2.5651    2.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -5.0193   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724   -5.9277    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   -5.4813    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -3.6317    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -3.1494    1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5453   -1.2183    3.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1201    1.1692    3.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9869   -1.3814    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    2.0883    2.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0053    2.7630   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    3.7992   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    4.7179   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    4.7104    0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    3.2337    2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256    3.3298    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038    5.1393    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    4.4681    3.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587    4.7637    2.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0
  8  9  2  0
  3  2  1  0
 12 21  1  0
  2  1  1  0
  9 10  1  0
 12 13  1  0
 11  9  1  0
 10  5  2  0
 18 16  2  0
  8 24  1  0
 16 15  1  0
  5  6  1  0
 15 14  2  0
 14 13  1  0
 24 21  1  0
 13 20  2  0
 20 18  1  0
  6  7  2  0
 21 22  1  0
  7  8  1  0
 22 23  1  0
 12 11  1  0
 18 19  1  0
  5  4  1  0
 16 17  1  0
 12 33  1  1
 21 39  1  6
 10 32  1  0
  6 30  1  0
  7 31  1  0
  4 29  1  0
  3 28  1  0
  2 26  1  0
  2 27  1  0
  1 25  1  0
 15 35  1  0
 14 34  1  0
 20 38  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 19 37  1  0
 17 36  1  0
M  END


  Mrv1652306192123583D          

 42 44  0  0  0  0            999 V2000
    1.9247   -5.6605   -0.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -5.2934    1.0845 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1767   -3.8603    1.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010   -2.8994    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.4883    1.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690   -0.7469    2.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318    0.6067    2.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    1.2343    2.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4350    0.5048    1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778   -0.8436    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    1.0470    0.9292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405    2.3117    1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1165    2.9269    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    3.0980   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079    3.6833   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    4.1000   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975    4.6802   -1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    3.9335    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4682    4.3471    0.9905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    3.3515    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2123    3.1939    1.6661 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9048    4.5665    2.2738 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1055    5.3370    2.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636    2.5651    2.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -5.0193   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724   -5.9277    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   -5.4813    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -3.6317    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -3.1494    1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5453   -1.2183    3.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1201    1.1692    3.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9869   -1.3814    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    2.0883    2.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0053    2.7630   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    3.7992   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    4.7179   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    4.7104    0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    3.2337    2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256    3.3298    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038    5.1393    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    4.4681    3.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587    4.7637    2.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  9  2  0  0  0  0
  3  2  1  0  0  0  0
 12 21  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 11  9  1  0  0  0  0
 10  5  2  0  0  0  0
 18 16  2  0  0  0  0
  8 24  1  0  0  0  0
 16 15  1  0  0  0  0
  5  6  1  0  0  0  0
 15 14  2  0  0  0  0
 14 13  1  0  0  0  0
 24 21  1  0  0  0  0
 13 20  2  0  0  0  0
 20 18  1  0  0  0  0
  6  7  2  0  0  0  0
 21 22  1  0  0  0  0
  7  8  1  0  0  0  0
 22 23  1  0  0  0  0
 12 11  1  0  0  0  0
 18 19  1  0  0  0  0
  5  4  1  0  0  0  0
 16 17  1  0  0  0  0
 12 33  1  1  0  0  0
 21 39  1  6  0  0  0
 10 32  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  0  0  0  0
  4 29  1  0  0  0  0
  3 28  1  0  0  0  0
  2 26  1  0  0  0  0
  2 27  1  0  0  0  0
  1 25  1  0  0  0  0
 15 35  1  0  0  0  0
 14 34  1  0  0  0  0
 20 38  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
 23 42  1  0  0  0  0
 19 37  1  0  0  0  0
 17 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030681

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC2=C(O[C@]1([H])C([H])([H])O[H])C([H])=C([H])C(\C([H])=C(/[H])C([H])([H])O[H])=C2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c19-7-1-2-11-3-6-15-16(8-11)24-18(17(10-20)23-15)12-4-5-13(21)14(22)9-12/h1-6,8-9,17-22H,7,10H2/b2-1+/t17-,18-/m1/s1

> <INCHI_KEY>
PPZYUSOIUGJLFB-ZHEVZCJESA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.336

> <EXACT_MASS>
330.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.88932137339097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2R,3R)-3-(hydroxymethyl)-7-[(1E)-3-hydroxyprop-1-en-1-yl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.8757188493333334

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.653420041336386

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207264099808981

> <JCHEM_PKA_STRONGEST_BASIC>
-2.526351815652445

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
88.35700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoamericanol A

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    1.9247   -5.6605   -0.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -5.2934    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -3.8603    1.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010   -2.8994    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.4883    1.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690   -0.7469    2.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318    0.6067    2.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    1.2343    2.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4350    0.5048    1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778   -0.8436    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    1.0470    0.9292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405    2.3117    1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1165    2.9269    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    3.0980   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079    3.6833   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    4.1000   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975    4.6802   -1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    3.9335    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4682    4.3471    0.9905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    3.3515    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2123    3.1939    1.6661 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9048    4.5665    2.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055    5.3370    2.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636    2.5651    2.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -5.0193   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724   -5.9277    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   -5.4813    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -3.6317    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -3.1494    1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5453   -1.2183    3.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1201    1.1692    3.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9869   -1.3814    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    2.0883    2.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0053    2.7630   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    3.7992   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    4.7179   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    4.7104    0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    3.2337    2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256    3.3298    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038    5.1393    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    4.4681    3.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587    4.7637    2.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0
  8  9  2  0
  3  2  1  0
 12 21  1  0
  2  1  1  0
  9 10  1  0
 12 13  1  0
 11  9  1  0
 10  5  2  0
 18 16  2  0
  8 24  1  0
 16 15  1  0
  5  6  1  0
 15 14  2  0
 14 13  1  0
 24 21  1  0
 13 20  2  0
 20 18  1  0
  6  7  2  0
 21 22  1  0
  7  8  1  0
 22 23  1  0
 12 11  1  0
 18 19  1  0
  5  4  1  0
 16 17  1  0
 12 33  1  1
 21 39  1  6
 10 32  1  0
  6 30  1  0
  7 31  1  0
  4 29  1  0
  3 28  1  0
  2 26  1  0
  2 27  1  0
  1 25  1  0
 15 35  1  0
 14 34  1  0
 20 38  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 19 37  1  0
 17 36  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0       1.925  -5.660  -0.158  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.501  -5.293   1.085  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.177  -3.860   1.348  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.101  -2.899   1.508  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.791  -1.488   1.780  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.669  -0.747   2.583  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.432   0.607   2.840  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.322   1.234   2.282  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.435   0.505   1.491  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.678  -0.844   1.224  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.310   1.047   0.929  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.041   2.312   1.525  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.117   2.927   0.650  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.921   3.098  -0.734  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.908   3.683  -1.534  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.095   4.100  -0.947  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.098   4.680  -1.673  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.299   3.934   0.420  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.468   4.347   0.991  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.326   3.352   1.221  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.212   3.194   1.666  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.905   4.566   2.274  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.106   5.337   2.377  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.164   2.565   2.559  0.00  0.00           O+0
HETATM   25  H   UNK     0       2.243  -5.019  -0.816  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.072  -5.928   1.866  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.578  -5.481   1.040  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.116  -3.632   1.426  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.159  -3.149   1.460  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.545  -1.218   3.023  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.120   1.169   3.464  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.987  -1.381   0.580  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.458   2.088   2.517  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.005   2.763  -1.200  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.731   3.799  -2.598  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.814   4.718  -2.603  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.988   4.710   0.246  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.521   3.234   2.284  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.726   3.330   0.704  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.204   5.139   1.661  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.494   4.468   3.284  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.759   4.764   2.821  0.00  0.00           H+0
CONECT    1    2   25                                                       
CONECT    2    3    1   26   27                                             
CONECT    3    4    2   28                                                  
CONECT    4    3    5   29                                                  
CONECT    5   10    6    4                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8   31                                                  
CONECT    8    9   24    7                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5   32                                                  
CONECT   11    9   12                                                       
CONECT   12   21   13   11   33                                             
CONECT   13   12   14   20                                                  
CONECT   14   15   13   34                                                  
CONECT   15   16   14   35                                                  
CONECT   16   18   15   17                                                  
CONECT   17   16   36                                                       
CONECT   18   16   20   19                                                  
CONECT   19   18   37                                                       
CONECT   20   13   18   38                                                  
CONECT   21   12   24   22   39                                             
CONECT   22   21   23   40   41                                             
CONECT   23   22   42                                                       
CONECT   24    8   21                                                       
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    2                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32   10                                                            
CONECT   33   12                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   19                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
CONECT   40   22                                                            
CONECT   41   22                                                            
CONECT   42   23                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

RDKit          3D

42 44  0  0  0  0  0  0  0  0999 V2000
    1.9247   -5.6605   -0.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -5.2934    1.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767   -3.8603    1.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010   -2.8994    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7911   -1.4883    1.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690   -0.7469    2.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4318    0.6067    2.8396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3219    1.2343    2.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4350    0.5048    1.4908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778   -0.8436    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3098    1.0470    0.9292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405    2.3117    1.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1165    2.9269    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9208    3.0980   -0.7344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9079    3.6833   -1.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    4.1000   -0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975    4.6802   -1.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2986    3.9335    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4682    4.3471    0.9905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3262    3.3515    1.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2123    3.1939    1.6661 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9048    4.5665    2.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055    5.3370    2.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1636    2.5651    2.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -5.0193   -0.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724   -5.9277    1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   -5.4813    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -3.6317    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1590   -3.1494    1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5453   -1.2183    3.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1201    1.1692    3.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9869   -1.3814    0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    2.0883    2.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0053    2.7630   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    3.7992   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8138    4.7179   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879    4.7104    0.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    3.2337    2.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256    3.3298    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2038    5.1393    1.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4937    4.4681    3.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587    4.7637    2.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0
  8  9  2  0
  3  2  1  0
 12 21  1  0
  2  1  1  0
  9 10  1  0
 12 13  1  0
 11  9  1  0
 10  5  2  0
 18 16  2  0
  8 24  1  0
 16 15  1  0
  5  6  1  0
 15 14  2  0
 14 13  1  0
 24 21  1  0
 13 20  2  0
 20 18  1  0
  6  7  2  0
 21 22  1  0
  7  8  1  0
 22 23  1  0
 12 11  1  0
 18 19  1  0
  5  4  1  0
 16 17  1  0
 12 33  1  1
 21 39  1  6
 10 32  1  0
  6 30  1  0
  7 31  1  0
  4 29  1  0
  3 28  1  0
  2 26  1  0
  2 27  1  0
  1 25  1  0
 15 35  1  0
 14 34  1  0
 20 38  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 19 37  1  0
 17 36  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3360 Da

Monoisotopic Mass

330.11034 Da

IUPAC Name

4-[(2R,3R)-3-(hydroxymethyl)-7-[(1E)-3-hydroxyprop-1-en-1-yl]-2,3-dihydro-1,4-benzodioxin-2-yl]benzene-1,2-diol

Traditional Name

isoamericanol A

CAS Registry Number

Not Available

SMILES

[H]OC1=C(O[H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC2=C(O[C@]1([H])C([H])([H])O[H])C([H])=C([H])C(\C([H])=C(/[H])C([H])([H])O[H])=C2[H]

InChI Identifier

InChI=1S/C18H18O6/c19-7-1-2-11-3-6-15-16(8-11)24-18(17(10-20)23-15)12-4-5-13(21)14(22)9-12/h1-6,8-9,17-22H,7,10H2/b2-1+/t17-,18-/m1/s1

InChI Key

PPZYUSOIUGJLFB-ZHEVZCJESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 360 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 360 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Capparis flavicans	Plant	KNApSAcK
Joannesia princeps	JEOL database	Waibel, R., et al., Phytochemistry 62, 805 (2003)
Phytolacca americana	FooDB	KNAPSACK
Phytolocca americana	-	KNApSAcK

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
Cinnamyl alcohol
Catechol
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Para-dioxin
Benzenoid
Ether
Oxacycle
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.83	ALOGPS
logP	1.88	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.36 m³·mol⁻¹	ChemAxon
Polarizability	34.89 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4947965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6444016

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Waibel R, Benirschke G, Benirschke M, Achenbach H: Sesquineolignans and other constituents from the seeds of Joannesia princeps. Phytochemistry. 2003 Mar;62(5):805-11. doi: 10.1016/s0031-9422(02)00357-6. [PubMed:12620334 ]
Li X, Li L, Wang J, Wang T, Wang L: Two new lignans with antioxidative activities from Jatropha curcas. Nat Prod Res. 2014;28(22):1985-91. doi: 10.1080/14786419.2014.919284. Epub 2014 May 28. [PubMed:24870973 ]
Kim KH, Moon E, Kim SY, Lee KR: Lignans from the tuber-barks of Colocasia antiquorum var. esculenta and their antimelanogenic Activity. J Agric Food Chem. 2010 Apr 28;58(8):4779-85. doi: 10.1021/jf100323q. [PubMed:20359228 ]
Etoh H, Murakami K, Yogoh T, Ishikawa H, Fukuyama Y, Tanaka H: Anti-oxidative compounds in barley tea. Biosci Biotechnol Biochem. 2004 Dec;68(12):2616-8. doi: 10.1271/bbb.68.2616. [PubMed:15618635 ]
Katagi A, Sui L, Kamitori K, Suzuki T, Katayama T, Hossain A, Noguchi C, Dong Y, Yamaguchi F, Tokuda M: Inhibitory effect of isoamericanol A from Jatropha curcas seeds on the growth of MCF-7 human breast cancer cell line by G2/M cell cycle arrest. Heliyon. 2016 Jan 6;2(1):e00055. doi: 10.1016/j.heliyon.2015.e00055. eCollection 2016 Jan. [PubMed:27441238 ]
Waibel, R., et al. (2003). Waibel, R., et al., Phytochemistry 62, 805 (2003). Phytochem..

Showing NP-Card for isoamericanol A (NP0030681)

MOL for NP0030681 (isoamericanol A )

3D MOL for NP0030681 (isoamericanol A )

3D SDF for NP0030681 (isoamericanol A )

3D-SDF for NP0030681 (isoamericanol A )

PDB for NP0030681 (isoamericanol A )

3D PDB for NP0030681 (isoamericanol A )

SMILES for NP0030681 (isoamericanol A )

INCHI for NP0030681 (isoamericanol A )

Structure for NP0030681 (isoamericanol A )

3D Structure for NP0030681 (isoamericanol A )