NP-MRD: Showing NP-Card for isosojagol (NP0039391)

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Record Information

Version

2.0

Created at

2021-06-20 21:50:13 UTC

Updated at

2021-08-20 00:00:38 UTC

NP-MRD ID

NP0039391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isosojagol

Provided By

JEOL Database JEOL Logo

Description

Isosojagol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, isosojagol is considered to be a flavonoid. Isosojagol has been detected, but not quantified in, pulses and scarlet beans (Phaseolus coccineus). This could make isosojagol a potential biomarker for the consumption of these foods. Isosojagol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. isosojagol is found in Erythrina abyssinica and Glycine max. isosojagol was first documented in 2019 (PMID: 30278472). Based on a literature review a small amount of articles have been published on Isosojagol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306202123503D          

 41 44  0  0  0  0            999 V2000
    0.3452   -5.4671    2.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072   -4.3471    3.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -4.7816    4.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151   -3.0519    2.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -2.4213    1.8585 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8929   -1.6503    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882   -2.2580   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -3.6194   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2166   -1.5249   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -0.1269   -1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    0.5269   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9132   -0.2467    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    0.5664    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    1.8313    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1031    2.9672    2.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.9153    3.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322    4.1103    3.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    5.3389    3.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    6.4677    3.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708    5.4080    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    4.2123    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    4.2910    0.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    3.1490   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    3.2636   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3069    1.8766    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -5.1412    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739   -5.9545    3.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -6.2153    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -5.2279    5.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9081   -5.5245    3.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459   -3.9470    4.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921   -2.3371    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955   -1.7502    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -3.1483    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -4.0198    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -2.0493   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4355   -2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9237    1.9625    3.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6156    4.0858    4.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    7.2457    3.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    6.3551    1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 25  1  0  0  0  0
 17 16  1  0  0  0  0
 11 12  1  0  0  0  0
 16 15  2  0  0  0  0
 12  6  2  0  0  0  0
 18 17  2  0  0  0  0
  6  7  1  0  0  0  0
 21 22  1  0  0  0  0
  7  9  2  0  0  0  0
 15 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 25 23  1  0  0  0  0
  6  5  1  0  0  0  0
 23 22  1  0  0  0  0
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 25 14  2  0  0  0  0
  4  2  2  3  0  0  0
 21 20  2  0  0  0  0
  2  1  1  0  0  0  0
 20 18  1  0  0  0  0
  2  3  1  0  0  0  0
 21 15  1  0  0  0  0
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 14 13  1  0  0  0  0
 18 19  1  0  0  0  0
 13 12  1  0  0  0  0
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 10 37  1  0  0  0  0
  5 33  1  0  0  0  0
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  4 32  1  0  0  0  0
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  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  8 35  1  0  0  0  0
 19 40  1  0  0  0  0
M  END

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    0.3452   -5.4671    2.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072   -4.3471    3.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -4.7816    4.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151   -3.0519    2.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -2.4213    1.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8929   -1.6503    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882   -2.2580   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -3.6194   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2166   -1.5249   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -0.1269   -1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    0.5269   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9132   -0.2467    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    0.5664    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    1.8313    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1031    2.9672    2.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.9153    3.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322    4.1103    3.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    5.3389    3.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    6.4677    3.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708    5.4080    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    4.2123    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    4.2910    0.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    3.1490   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    3.2636   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3069    1.8766    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -5.1412    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739   -5.9545    3.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -6.2153    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -5.2279    5.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9081   -5.5245    3.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459   -3.9470    4.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921   -2.3371    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955   -1.7502    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -3.1483    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -4.0198    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -2.0493   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4355   -2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9237    1.9625    3.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6156    4.0858    4.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    7.2457    3.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    6.3551    1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 25  1  0
 17 16  1  0
 11 12  1  0
 16 15  2  0
 12  6  2  0
 18 17  2  0
  6  7  1  0
 21 22  1  0
  7  9  2  0
 15 14  1  0
  9 10  1  0
 10 11  2  0
 25 23  1  0
  6  5  1  0
 23 22  1  0
  5  4  1  0
 25 14  2  0
  4  2  2  3
 21 20  2  0
  2  1  1  0
 20 18  1  0
  2  3  1  0
 21 15  1  0
  7  8  1  0
 14 13  1  0
 18 19  1  0
 13 12  1  0
 23 24  2  0
 17 39  1  0
 16 38  1  0
 20 41  1  0
  9 36  1  0
 10 37  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  8 35  1  0
 19 40  1  0
M  END

  Mrv1652306202123503D          

 41 44  0  0  0  0            999 V2000
    0.3452   -5.4671    2.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072   -4.3471    3.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -4.7816    4.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151   -3.0519    2.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -2.4213    1.8585 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8929   -1.6503    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882   -2.2580   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -3.6194   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2166   -1.5249   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -0.1269   -1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    0.5269   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9132   -0.2467    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    0.5664    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    1.8313    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1031    2.9672    2.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.9153    3.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322    4.1103    3.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    5.3389    3.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    6.4677    3.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708    5.4080    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    4.2123    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    4.2910    0.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    3.1490   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    3.2636   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3069    1.8766    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -5.1412    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739   -5.9545    3.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -6.2153    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -5.2279    5.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8459   -3.9470    4.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921   -2.3371    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955   -1.7502    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -3.1483    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -4.0198    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -2.0493   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4355   -2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9237    1.9625    3.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6156    4.0858    4.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    7.2457    3.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    6.3551    1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 25  1  0  0  0  0
 17 16  1  0  0  0  0
 11 12  1  0  0  0  0
 16 15  2  0  0  0  0
 12  6  2  0  0  0  0
 18 17  2  0  0  0  0
  6  7  1  0  0  0  0
 21 22  1  0  0  0  0
  7  9  2  0  0  0  0
 15 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 25 23  1  0  0  0  0
  6  5  1  0  0  0  0
 23 22  1  0  0  0  0
  5  4  1  0  0  0  0
 25 14  2  0  0  0  0
  4  2  2  3  0  0  0
 21 20  2  0  0  0  0
  2  1  1  0  0  0  0
 20 18  1  0  0  0  0
  2  3  1  0  0  0  0
 21 15  1  0  0  0  0
  7  8  1  0  0  0  0
 14 13  1  0  0  0  0
 18 19  1  0  0  0  0
 13 12  1  0  0  0  0
 23 24  2  0  0  0  0
 17 39  1  0  0  0  0
 16 38  1  0  0  0  0
 20 41  1  0  0  0  0
  9 36  1  0  0  0  0
 10 37  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  4 32  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 29  1  0  0  0  0
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  8 35  1  0  0  0  0
 19 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C3=C(C4=C([H])C([H])=C(O[H])C(=C4O3)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C(=O)OC2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-17-19(25-18(12)14)13-6-4-11(21)9-16(13)24-20(17)23/h3-4,6-9,21-22H,5H2,1-2H3

> <INCHI_KEY>
MQKLGUOASGICKG-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
35.80342990592937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
4.125888321666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.443727154110311

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.093799044908984

> <JCHEM_PKA_STRONGEST_BASIC>
-3.06082027963857

> <JCHEM_POLAR_SURFACE_AREA>
79.9

> <JCHEM_REFRACTIVITY>
93.86229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,14-dihydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    0.3452   -5.4671    2.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072   -4.3471    3.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -4.7816    4.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151   -3.0519    2.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -2.4213    1.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8929   -1.6503    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882   -2.2580   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -3.6194   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2166   -1.5249   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -0.1269   -1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    0.5269   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9132   -0.2467    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    0.5664    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    1.8313    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1031    2.9672    2.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.9153    3.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322    4.1103    3.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    5.3389    3.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    6.4677    3.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708    5.4080    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    4.2123    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    4.2910    0.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    3.1490   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    3.2636   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3069    1.8766    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -5.1412    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739   -5.9545    3.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -6.2153    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -5.2279    5.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9081   -5.5245    3.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459   -3.9470    4.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921   -2.3371    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955   -1.7502    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -3.1483    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -4.0198    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -2.0493   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4355   -2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9237    1.9625    3.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6156    4.0858    4.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    7.2457    3.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    6.3551    1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 25  1  0
 17 16  1  0
 11 12  1  0
 16 15  2  0
 12  6  2  0
 18 17  2  0
  6  7  1  0
 21 22  1  0
  7  9  2  0
 15 14  1  0
  9 10  1  0
 10 11  2  0
 25 23  1  0
  6  5  1  0
 23 22  1  0
  5  4  1  0
 25 14  2  0
  4  2  2  3
 21 20  2  0
  2  1  1  0
 20 18  1  0
  2  3  1  0
 21 15  1  0
  7  8  1  0
 14 13  1  0
 18 19  1  0
 13 12  1  0
 23 24  2  0
 17 39  1  0
 16 38  1  0
 20 41  1  0
  9 36  1  0
 10 37  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  8 35  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.345  -5.467   2.696  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.207  -4.347   3.211  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.233  -4.782   4.227  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.115  -3.052   2.848  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.171  -2.421   1.859  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.893  -1.650   0.786  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.588  -2.258  -0.278  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.692  -3.619  -0.393  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.217  -1.525  -1.287  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.203  -0.127  -1.276  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.539   0.527  -0.225  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.913  -0.247   0.758  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.319   0.566   1.690  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.572   1.831   1.295  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.103   2.967   2.034  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.643   2.915   3.207  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.032   4.110   3.820  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.675   5.339   3.258  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.085   6.468   3.905  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.071   5.408   2.086  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.452   4.212   1.486  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.219   4.291   0.281  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.673   3.149  -0.435  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.329   3.264  -1.464  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.307   1.877   0.141  0.00  0.00           C+0
HETATM   26  H   UNK     0      -0.417  -5.141   1.986  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.174  -5.955   3.528  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.965  -6.215   2.191  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.740  -5.228   5.097  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.908  -5.524   3.789  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.846  -3.947   4.585  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.792  -2.337   3.319  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.496  -1.750   2.415  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.488  -3.148   1.375  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.510  -4.020   0.474  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.731  -2.049  -2.089  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.699   0.436  -2.062  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.924   1.962   3.647  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.616   4.086   4.737  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.774   7.246   3.413  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.354   6.355   1.641  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   29   30   31                                             
CONECT    4    5    2   32                                                  
CONECT    5    6    4   33   34                                             
CONECT    6   12    7    5                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7   35                                                       
CONECT    9    7   10   36                                                  
CONECT   10    9   11   37                                                  
CONECT   11   25   12   10                                                  
CONECT   12   11    6   13                                                  
CONECT   13   14   12                                                       
CONECT   14   15   25   13                                                  
CONECT   15   16   14   21                                                  
CONECT   16   17   15   38                                                  
CONECT   17   16   18   39                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   40                                                       
CONECT   20   21   18   41                                                  
CONECT   21   22   20   15                                                  
CONECT   22   21   23                                                       
CONECT   23   25   22   24                                                  
CONECT   24   23                                                            
CONECT   25   11   23   14                                                  
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

RDKit          3D

41 44  0  0  0  0  0  0  0  0999 V2000
    0.3452   -5.4671    2.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072   -4.3471    3.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -4.7816    4.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151   -3.0519    2.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -2.4213    1.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8929   -1.6503    0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882   -2.2580   -0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918   -3.6194   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2166   -1.5249   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -0.1269   -1.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    0.5269   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9132   -0.2467    0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    0.5664    1.6901 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    1.8313    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1031    2.9672    2.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.9153    3.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322    4.1103    3.8195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749    5.3389    3.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    6.4677    3.9046 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708    5.4080    2.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    4.2123    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2186    4.2910    0.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733    3.1490   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288    3.2636   -1.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3069    1.8766    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -5.1412    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739   -5.9545    3.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652   -6.2153    2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7403   -5.2279    5.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9081   -5.5245    3.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459   -3.9470    4.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7921   -2.3371    3.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4955   -1.7502    2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -3.1483    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5097   -4.0198    0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7310   -2.0493   -2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4355   -2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9237    1.9625    3.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6156    4.0858    4.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7737    7.2457    3.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539    6.3551    1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 25  1  0
 17 16  1  0
 11 12  1  0
 16 15  2  0
 12  6  2  0
 18 17  2  0
  6  7  1  0
 21 22  1  0
  7  9  2  0
 15 14  1  0
  9 10  1  0
 10 11  2  0
 25 23  1  0
  6  5  1  0
 23 22  1  0
  5  4  1  0
 25 14  2  0
  4  2  2  3
 21 20  2  0
  2  1  1  0
 20 18  1  0
  2  3  1  0
 21 15  1  0
  7  8  1  0
 14 13  1  0
 18 19  1  0
 13 12  1  0
 23 24  2  0
 17 39  1  0
 16 38  1  0
 20 41  1  0
  9 36  1  0
 10 37  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  8 35  1  0
 19 40  1  0
M  END

View in JSmol

Synonyms

Value	Source
3,9-Dihydroxy-10-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one	ChEBI
3,9-Dihydroxy-10-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one	ChEBI
3,9-Dihydroxy-10-prenylcoumestan	ChEBI
3,9-Dihydroxy-10-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₆O₅

Average Mass

336.3380 Da

Monoisotopic Mass

336.09977 Da

IUPAC Name

5,14-dihydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

5,14-dihydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C3=C(C4=C([H])C([H])=C(O[H])C(=C4O3)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C(=O)OC2=C1[H]

InChI Identifier

InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-17-19(25-18(12)14)13-6-4-11(21)9-16(13)24-20(17)23/h3-4,6-9,21-22H,5H2,1-2H3

InChI Key

MQKLGUOASGICKG-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Erythrina abyssinica	JEOL database	Nguyen, P.-H., et al, J. Nat. Prod. 73, 598 (2010)
Glycine max	LOTUS Database	35616633
Phaseolus coccineus	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Not Available

Substituents

Not Available

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	0.98 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.63	ALOGPS
logP	4.13	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.09	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.86 m³·mol⁻¹	ChemAxon
Polarizability	35.8 Å³	ChemAxon
Number of Rings	4	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

HMDB0030141

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001947

KNApSAcK ID

C00010050

Chemspider ID

20575877

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16744613

PDB ID

Not Available

ChEBI ID

142265

Good Scents ID

rw1817371

References

General References

Jiang MY, Luo M, Tian K, Li YH, Sun JX, Lu Y, Pu XY, Huang XZ: alpha-Glucosidase Inhibitory and Anti-Inflammatory Coumestans from the Roots of Dolichos trilobus. Planta Med. 2019 Jan;85(2):112-117. doi: 10.1055/a-0746-8622. Epub 2018 Oct 2. [PubMed:30278472 ]
Nguyen, P.-H., et al. (2010). Nguyen, P.-H., et al, J. Nat. Prod. 73, 598 (2010). J. Nat. Prod..

Showing NP-Card for isosojagol (NP0039391)

MOL for NP0039391 (isosojagol)

3D MOL for NP0039391 (isosojagol)

3D SDF for NP0039391 (isosojagol)

3D-SDF for NP0039391 (isosojagol)

PDB for NP0039391 (isosojagol)

3D PDB for NP0039391 (isosojagol)

SMILES for NP0039391 (isosojagol)

INCHI for NP0039391 (isosojagol)

Structure for NP0039391 (isosojagol)

3D Structure for NP0039391 (isosojagol)