NP-MRD: Showing NP-Card for 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid (NP0252224)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 15:39:54 UTC

Updated at

2022-09-07 15:39:54 UTC

NP-MRD ID

NP0252224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid

Description

Medicarpin 3-O-glucoside-6'-malonate belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Medicarpin 3-O-glucoside-6'-malonate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid is found in Maackia amurensis. Based on a literature review very few articles have been published on Medicarpin 3-O-glucoside-6'-malonate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217392D          

 37 41  0  0  1  0            999 V2000
   -1.2387   -2.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -2.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5692   -4.0418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3929   -4.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7639   -4.8258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5875   -4.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0402   -4.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8638   -4.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2348   -4.9673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3165   -3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1401   -3.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5928   -2.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5111   -4.3247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3112   -5.5156    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6822   -6.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876   -5.4684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0349   -6.1582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -4.7315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2929   -4.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  1  1  0  0  0
 14 33  1  0  0  0  0
 33 34  2  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37  6  1  1  0  0  0
 10 37  1  0  0  0  0
M  END

     RDKit          3D

 63 67  0  0  0  0  0  0  0  0999 V2000
    8.4872    2.8366    3.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9983    1.8238    2.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1006    1.1466    1.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5462    0.1492    1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6831   -0.5361    0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3396   -0.2355    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8669    0.7580    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7531    1.4247    1.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4749    0.9051    0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0484   -0.3756    0.4154 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7426   -0.1944   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990    0.0229    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3641    0.1688   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    0.1076   -1.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0659    0.2450   -2.0382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2756    0.5178   -1.3881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8554   -0.7054   -0.9705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0666   -0.3565   -0.3095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2982   -1.1815    0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4782   -0.9744    1.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7061   -1.3913    1.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9250   -2.0828    0.1885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9103   -1.0494    2.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1032   -1.7420    1.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3810   -2.8993    1.9019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9090   -1.1185    0.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1075   -0.1603   -1.3293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1686    0.5812   -0.8469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5080    0.5727   -2.5506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2938   -0.3302   -3.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621    1.3024   -2.1493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6113    2.4450   -1.3876 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3202   -0.1074   -2.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712   -0.2553   -1.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6912   -0.4654   -2.4297 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985   -0.2846   -1.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356   -0.7407   -0.5226 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0475    3.6698    3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2502    3.1634    4.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414    2.4331    4.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5928   -0.0991    1.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0225   -1.3123   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3977    2.2049    2.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9452   -1.0881    1.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7607    0.0694    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966    0.3399    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0313    1.0606   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8065    0.6928    0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4711   -0.9306    1.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1553   -2.3030    0.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7121   -1.3556    3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0662    0.0499    1.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5539   -0.4038   -0.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4663   -1.1127   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9763    0.4196   -1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2540    1.2949   -2.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2837   -1.2551   -3.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    1.7251   -3.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9200    3.1366   -1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -0.1567   -3.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6846   -0.8536   -2.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2385    0.7921   -1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2162   -1.8803   -0.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 37  1  0
 37 36  1  0
 36 35  1  0
 35 34  1  0
 34 33  2  0
 33 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 26  1  0
 24 25  2  0
 18 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  8  3  1  0
  7  6  1  0
 10 37  1  0
 11 34  1  0
 31 16  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  5 42  1  0
 37 63  1  6
 36 61  1  0
 36 62  1  0
 33 60  1  0
 16 47  1  1
 18 48  1  1
 19 49  1  0
 19 50  1  0
 23 51  1  0
 23 52  1  0
 26 53  1  0
 27 54  1  6
 28 55  1  0
 29 56  1  6
 30 57  1  0
 31 58  1  6
 32 59  1  0
 13 46  1  0
 12 45  1  0
 10 44  1  1
  8 43  1  0
M  END


  Mrv1652309072217392D          

 37 41  0  0  1  0            999 V2000
   -1.2387   -2.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -2.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5692   -4.0418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3929   -4.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7639   -4.8258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5875   -4.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0402   -4.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8638   -4.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2348   -4.9673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3165   -3.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1401   -3.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5928   -2.8981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5111   -4.3247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3112   -5.5156    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6822   -6.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876   -5.4684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0349   -6.1582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -4.7315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2929   -4.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  1  1  0  0  0
 14 33  1  0  0  0  0
 33 34  2  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37  6  1  1  0  0  0
 10 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2[C@@H]3COC4=CC(O[C@@H]5O[C@H](COC(=O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]5O)=CC=C4[C@@H]3OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O12/c1-32-11-2-4-13-15-9-33-16-7-12(3-5-14(16)24(15)36-17(13)6-11)35-25-23(31)22(30)21(29)18(37-25)10-34-20(28)8-19(26)27/h2-7,15,18,21-25,29-31H,8-10H2,1H3,(H,26,27)/t15-,18+,21+,22-,23+,24-,25+/m0/s1

> <INCHI_KEY>
BQAJKXKYTQTBDK-PCHDOLKHSA-N

> <FORMULA>
C25H26O12

> <MOLECULAR_WEIGHT>
518.471

> <EXACT_MASS>
518.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.014638538738986

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid

> <JCHEM_LOGP>
0.5745091593333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.201707345883293

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.399538613951725

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64910302537729

> <JCHEM_POLAR_SURFACE_AREA>
170.44

> <JCHEM_REFRACTIVITY>
120.70110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.312  -5.414   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.017  -4.582   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.352  -5.287   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.425  -6.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.794  -7.531   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.090  -6.699   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.016  -5.161   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.648  -4.455   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.457  -4.616   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.420  -5.817   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.958  -5.905   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.803  -4.618   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.340  -4.706   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.033  -6.081   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.570  -6.169   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.263  -7.545   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.800  -7.633   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.493  -9.008   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.030  -9.096   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.875  -7.809   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      18.413  -7.897   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      19.105  -9.272   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      19.257  -6.609   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.795  -6.697   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      21.640  -5.410   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      21.487  -8.073   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.648 -10.296   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.340 -11.671   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.110 -10.208   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.265 -11.495   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.418  -8.832   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.880  -8.744   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.188  -7.369   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.650  -7.281   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.805  -8.568   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.268  -8.480   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.575  -7.105   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   37                                                  
CONECT   11   10   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   18   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   16   32                                                  
CONECT   32   31                                                            
CONECT   33   14   34                                                       
CONECT   34   33   11   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    6   10                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
Medicarpin 3-O-glucoside-6'-malonic acid	Generator

Chemical Formula

C₂₅H₂₆O₁₂

Average Mass

518.4710 Da

Monoisotopic Mass

518.14243 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C2[C@@H]3COC4=CC(O[C@@H]5O[C@H](COC(=O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]5O)=CC=C4[C@@H]3OC2=C1

InChI Identifier

InChI=1S/C25H26O12/c1-32-11-2-4-13-15-9-33-16-7-12(3-5-14(16)24(15)36-17(13)6-11)35-25-23(31)22(30)21(29)18(37-25)10-34-20(28)8-19(26)27/h2-7,15,18,21-25,29-31H,8-10H2,1H3,(H,26,27)/t15-,18+,21+,22-,23+,24-,25+/m0/s1

InChI Key

BQAJKXKYTQTBDK-PCHDOLKHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Maackia amurensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Isoflavanol
Pterocarpan
Isoflavan
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzofuran
Anisole
Alkyl aryl ether
Dicarboxylic acid or derivatives
Benzenoid
1,3-dicarbonyl compound
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Ether
Acetal
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterocarpans (CHEBI:80391 )
pterocarpans (C16224 )
Pterocarpanes (C16224 )

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

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

24022786

KEGG Compound ID

C16224

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724665

PDB ID

Not Available

ChEBI ID

80391

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid (NP0252224)

MOL for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D MOL for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D SDF for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D-SDF for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

PDB for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D PDB for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

SMILES for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

INCHI for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

Structure for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)

3D Structure for NP0252224 (3-oxo-3-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(1r,10r)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-5-yl]oxy}oxan-2-yl]methoxy}propanoic acid)