NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate (NP0185174)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 00:30:32 UTC

Updated at

2022-09-04 00:30:32 UTC

NP-MRD ID

NP0185174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

Description

Cypellocarpin B belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. [(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate is found in Eucalyptus cypellocarpa. Based on a literature review very few articles have been published on cypellocarpin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202302D          

 38 41  0  0  1  0            999 V2000
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 29  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  1  0  0  0
 11 36  1  0  0  0  0
 36 37  2  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END

     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
    7.4569    1.8153    3.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1660    1.9263    2.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8373    3.1636    1.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6246    0.8034    1.6920 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6811    2.0567    2.0894 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4999    2.1501    0.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0951    1.9522    0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1463    1.5159    1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762    1.3763    0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5659    1.7225   -0.7214 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095    0.9159    1.1898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5910    0.8040    0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.1638    1.7986 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7035    0.0345    1.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1543   -1.1937    1.0173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5148   -1.5851   -0.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0495   -1.5854   -1.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263   -2.0853   -2.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728   -2.0777   -3.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1369   -2.5855   -4.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1579   -1.5704   -4.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8694   -1.0814   -2.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3029   -1.0971   -1.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1370   -0.5826   -3.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5564   -0.2161   -4.4549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0402    0.0743   -4.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8496    0.9372   -4.8176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2194   -1.3599   -5.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7256   -1.5713   -5.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0365   -1.7308   -6.3386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9752   -2.2605    2.0591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0865   -2.3557    2.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7074   -2.0212    2.8763 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0440   -3.2459    3.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7724   -1.1507    2.0823 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4306   -0.9259    2.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4370    1.1502    2.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9183    0.8823    2.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2512    0.8083    4.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9304    2.6213    4.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5419    1.9936    3.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8010    3.3338    2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0695    3.0617    0.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2212    4.0821    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2714    0.3506    2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2709    2.9923    2.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0615    1.2855    0.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8737    3.1125    0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7849    2.1997   -0.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0443    1.7628    0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    0.1016   -0.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3216    0.8475    2.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2730   -1.0986    0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3421   -2.4526   -2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2116   -2.9423   -4.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9513   -0.6832   -0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2011    1.1352   -4.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5234   -0.1422   -3.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5277   -0.5717   -5.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2991    0.8035   -5.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5100   -1.1258   -6.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7426   -2.2576   -4.9889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609   -3.2368    1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1460   -1.5895    3.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9012   -1.5334    3.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -3.5313    2.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361   -1.6237    1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501   -1.6473    2.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0780    1.9000    3.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.1951    2.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1367    0.7578    3.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1900   -0.0715    2.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5 38  1  0
 38 37  1  0
 37  8  1  0
  8  7  2  0
  7  6  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 29  1  0
 29 30  2  0
 29 28  1  0
 28 25  1  0
 25 26  1  0
 25 27  1  6
 25 24  1  0
 24 22  1  0
 22 23  2  0
 15 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
  6  5  1  0
 35 13  1  0
 23 17  1  0
 22 21  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  5 46  1  1
 38 71  1  0
 38 72  1  0
 37 69  1  0
 37 70  1  0
  7 49  1  0
  6 47  1  0
  6 48  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 15 53  1  6
 18 54  1  0
 20 55  1  0
 28 61  1  0
 28 62  1  0
 26 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 23 56  1  0
 31 63  1  6
 32 64  1  0
 33 65  1  1
 34 66  1  0
 35 67  1  6
 36 68  1  0
M  END


  Mrv1652309042202302D          

 38 41  0  0  1  0            999 V2000
   -0.0980   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 29  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  1  0  0  0
 11 36  1  0  0  0  0
 36 37  2  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1CCC(=CC1)C(=O)OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)CC(C)(O)OC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O12/c1-25(2,33)13-6-4-12(5-7-13)23(32)35-11-18-20(29)21(30)22(31)24(37-18)36-14-8-15(27)19-16(28)10-26(3,34)38-17(19)9-14/h4,8-9,13,18,20-22,24,27,29-31,33-34H,5-7,10-11H2,1-3H3/t13-,18+,20+,21-,22+,24+,26?/m0/s1

> <INCHI_KEY>
BNOXWGIIFHBMQJ-UOCJQAADSA-N

> <FORMULA>
C26H34O12

> <MOLECULAR_WEIGHT>
538.546

> <EXACT_MASS>
538.205026535

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.155234868771075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

> <JCHEM_LOGP>
1.233998439999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.714588718865349

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.596626875731653

> <JCHEM_PKA_STRONGEST_BASIC>
-0.873124645754053

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
129.90910000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.183  -2.043   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.807  -3.757   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003 -17.710   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.463 -16.170   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.543 -16.170   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   38                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   37                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   23   29                                                       
CONECT   29   28   20                                                       
CONECT   30   15   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   13   35                                                  
CONECT   35   34                                                            
CONECT   36   11   37                                                       
CONECT   37   36    7   38                                                  
CONECT   38   37    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₂

Average Mass

538.5460 Da

Monoisotopic Mass

538.20503 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

Traditional Name

[(2R,3S,4S,5R,6S)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1CCC(=CC1)C(=O)OC[C@H]1O[C@@H](OC2=CC(O)=C3C(=O)CC(C)(O)OC3=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C26H34O12/c1-25(2,33)13-6-4-12(5-7-13)23(32)35-11-18-20(29)21(30)22(31)24(37-18)36-14-8-15(27)19-16(28)10-26(3,34)38-17(19)9-14/h4,8-9,13,18,20-22,24,27,29-31,33-34H,5-7,10-11H2,1-3H3/t13-,18+,20+,21-,22+,24+,26?/m0/s1

InChI Key

BNOXWGIIFHBMQJ-UOCJQAADSA-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
Eucalyptus cypellocarpa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Phenolic glycoside
Alkyl glycoside
Glycosyl compound
Chromone
O-glycosyl compound
Monoterpenoid
Chromane
Benzopyran
1-benzopyran
P-menthane monoterpenoid
Aromatic monoterpenoid
Bicyclic monoterpenoid
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Benzenoid
Monosaccharide
Fatty acyl
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Carboxylic acid ester
Secondary alcohol
Hemiacetal
Ketone
Polyol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aldehyde
Organic oxygen 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	1.23	ChemAxon
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.91 m³·mol⁻¹	ChemAxon
Polarizability	54.16 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

C00046707

Chemspider ID

8681964

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10506563

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate (NP0185174)

MOL for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D MOL for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D SDF for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D-SDF for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

PDB for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D PDB for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

SMILES for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

INCHI for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

Structure for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D Structure for NP0185174 ([(2r,3s,4s,5r,6s)-6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (4r)-4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)