NP-MRD: Showing NP-Card for (-)-Clemastanin A (NP0071047)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 16:27:52 UTC

Updated at

2022-04-28 16:27:52 UTC

NP-MRD ID

NP0071047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Clemastanin A

Description

Clemastanin A belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (-)-Clemastanin A is found in Clematis stans, Rhodiola crenulata and Rhodiola crenulata (HOOK.f.et Thoms.) H.OHBA. (-)-Clemastanin A was first documented in 2017 (PMID: 29048378). Based on a literature review very few articles have been published on Clemastanin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218272D          

 36 39  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 20 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 68 71  0  0  0  0  0  0  0  0999 V2000
   -6.0747   -3.1369    1.8340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5522   -4.0962    0.9361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4257   -3.8300    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084   -2.5830    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987   -2.3016   -0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562   -1.0064   -0.3756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6231   -1.0959   -0.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1582    0.1883   -0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0108    0.8954   -0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9217    0.2129    0.4864 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1501    0.6542    0.9468 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1311   -0.1829    0.4307 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221   -0.9012    1.3702 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7167   -1.8826    0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5521   -1.0915   -0.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8174   -1.7243    2.1745 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4497   -2.6843    2.9569 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0754   -0.7207    3.0492 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7835   -1.1880    3.2153 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1297    0.6566    2.4562 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1497    1.4433    2.9659 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2311    2.1795   -0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2920    2.8179   -1.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5136    4.2137   -2.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563    5.1828   -1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876    6.5773   -1.5497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5484    6.7979   -1.7305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8561    2.1181   -1.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844    0.8335   -1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2083   -0.1216   -1.5785 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5463    0.5643   -1.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5207   -0.4348   -1.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2089   -3.2523   -1.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990   -4.4946   -1.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -4.7777   -0.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5470   -6.0089   -0.8246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4654   -2.2968    1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3088   -2.7147    2.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9003   -3.6366    2.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -1.8921    0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4359   -0.4257    0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4146    1.6748    0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4129   -0.3105    2.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -2.5042    1.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0606   -2.4428   -0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2846   -1.1142   -1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103   -2.1668    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542   -3.5902    2.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5616   -0.6702    4.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -0.7332    2.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696    1.1675    2.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870    2.0056    2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1348    2.7114   -0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571    4.3800   -3.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867    4.4511   -2.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1191    4.9740   -0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5128    5.0779   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2455    7.3605   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2796    6.6914   -2.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8924    7.2836   -0.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6043    2.6208   -2.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0831   -0.7324   -2.4944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5969    1.0950   -2.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7044    1.2787   -0.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5528   -0.8208   -2.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3268   -3.0729   -1.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4656   -5.2776   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3593   -6.1910   -0.2552 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 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 35  3  1  0
 30  6  1  0
 29  8  1  0
 20 11  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  0
 33 66  1  0
 34 67  1  0
 36 68  1  0
  6 41  1  1
 11 42  1  6
 13 43  1  1
 14 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  6
 17 48  1  0
 18 49  1  1
 19 50  1  0
 20 51  1  6
 21 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 28 61  1  0
 30 62  1  6
 31 63  1  0
 31 64  1  0
 32 65  1  0
M  END


  Mrv1652304282218272D          

 36 39  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  6  0  0  0
 17 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 20 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@H]1OC2=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C(CCCO)C=C2[C@@H]1CO

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O11/c1-33-17-9-13(4-5-16(17)29)23-15(10-27)14-7-12(3-2-6-26)8-18(24(14)36-23)34-25-22(32)21(31)20(30)19(11-28)35-25/h4-5,7-9,15,19-23,25-32H,2-3,6,10-11H2,1H3/t15-,19+,20+,21-,22+,23+,25+/m0/s1

> <INCHI_KEY>
WGTYXIDAEFJHPD-DJSGBOIRSA-N

> <FORMULA>
C25H32O11

> <MOLECULAR_WEIGHT>
508.52

> <EXACT_MASS>
508.19446185

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.4191375924998

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.27

> <JCHEM_LOGP>
-0.4574357189999998

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.201500808840638

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.907750487845366

> <JCHEM_PKA_STRONGEST_BASIC>
-2.377416082364493

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
125.15639999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.259   9.003   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.925  11.313   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.400   5.510   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.940   5.510   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.940   2.843   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.591  -0.237   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.925  -1.007   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.925  -2.547   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18                                                       
CONECT   18   17                                                            
CONECT   19    5   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20    4   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   24                                                       
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   27                                                            
CONECT   33    2   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₁₁

Average Mass

508.5200 Da

Monoisotopic Mass

508.19446 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-{[(2S,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-2,3-dihydro-1-benzofuran-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@H]1OC2=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C(CCCO)C=C2[C@@H]1CO

InChI Identifier

InChI=1S/C25H32O11/c1-33-17-9-13(4-5-16(17)29)23-15(10-27)14-7-12(3-2-6-26)8-18(24(14)36-23)34-25-22(32)21(31)20(30)19(11-28)35-25/h4-5,7-9,15,19-23,25-32H,2-3,6,10-11H2,1H3/t15-,19+,20+,21-,22+,23+,25+/m0/s1

InChI Key

WGTYXIDAEFJHPD-DJSGBOIRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Clematis stans	Plant	KNApSAcK
Rhodiola crenulata	LOTUS Database	35616633
Rhodiola crenulata (HOOK.f.et Thoms.) H.OHBA	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Lignan glycoside
Neolignan skeleton
Norlignan skeleton
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Benzofuran
Coumaran
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Polyol
Primary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	0.27	ALOGPS
logP	-0.46	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	125.16 m³·mol⁻¹	ChemAxon
Polarizability	52.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029992

Chemspider ID

62783402

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131849666

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu LL, Xu JJ, Zhong KR, Shang ZP, Wang F, Wang RF, Zhang L, Zhang JY, Liu B: Analysis of Non-Volatile Chemical Constituents of Menthae Haplocalycis Herba by Ultra-High Performance Liquid Chromatography-High Resolution Mass Spectrometry. Molecules. 2017 Oct 19;22(10):1756. doi: 10.3390/molecules22101756. [PubMed:29048378 ]

Showing NP-Card for (-)-Clemastanin A (NP0071047)

MOL for NP0071047 ((-)-Clemastanin A)

3D MOL for NP0071047 ((-)-Clemastanin A)

3D SDF for NP0071047 ((-)-Clemastanin A)

3D-SDF for NP0071047 ((-)-Clemastanin A)

PDB for NP0071047 ((-)-Clemastanin A)

3D PDB for NP0071047 ((-)-Clemastanin A)

SMILES for NP0071047 ((-)-Clemastanin A)

INCHI for NP0071047 ((-)-Clemastanin A)

Structure for NP0071047 ((-)-Clemastanin A)

3D Structure for NP0071047 ((-)-Clemastanin A)