NP-MRD: Showing NP-Card for 4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate (NP0144663)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-01 23:41:49 UTC

Updated at

2022-09-01 23:41:49 UTC

NP-MRD ID

NP0144663

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate

Description

Ganbajunin C, also known as vialinin a, belongs to the class of organic compounds known as p-terphenyls. These are terphenyls with a structure containing the 1,4-diphenylbenzene skeleton. 4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate is found in Thelephora aurantiotincta and Thelephora ganbajun. 4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate was first documented in 2003 (PMID: 12872944). Based on a literature review a small amount of articles have been published on ganbajunin C (PMID: 12895540) (PMID: 17850091).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022201412D          

 42 46  0  0  0  0            999 V2000
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  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
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  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
   -4.2868   -4.1250    0.0000 C   0  0  0  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
   -5.7158   -4.9500    0.0000 C   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  2  0  0  0  0
 21 36  1  0  0  0  0
 20 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 15 39  1  0  0  0  0
 39 40  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  2  0  0  0  0
 11 42  1  0  0  0  0
M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
    8.0208    2.6996   -0.9340 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1696    1.4895   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5982    0.9250   -1.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5372   -0.3650   -0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0155   -1.4326   -1.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8257   -2.6452   -0.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1577   -2.7845    0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6858   -1.7058    1.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8684   -0.4845    0.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375    0.6388   -1.2959 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8241    0.7798   -1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9050    1.1862   -2.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586    1.2993   -1.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460    0.9900   -0.6053 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6068    1.0144   -0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404    2.1294    0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6358    3.3162    0.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442    2.0291    0.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0896    3.1844    0.7449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1087    0.8650    0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5118    0.6648    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9551    0.3266    1.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2515    0.0282    2.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2548    0.0412    1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5304   -0.2762    1.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6814    0.3276    1.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8014    1.4482    0.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9375   -0.2954    1.6903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7674   -0.7303    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8482   -0.0145    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6281   -0.4286   -0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2809   -1.5803   -1.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1719   -2.3265   -1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4000   -1.9091   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8192    0.3759   -0.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4819    0.6827   -0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4024   -0.2672   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0608   -1.4689   -0.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312   -0.2078   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -1.3173   -0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9442    0.5784    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    0.4694    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3232    1.6290   -1.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6725    0.6733   -2.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7591   -1.3448   -2.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4185   -3.4547   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9803   -3.7619    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9294   -1.8488    2.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2690    0.3518    1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3201    1.4301   -3.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8683    1.6193   -2.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6505    3.3301    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968    4.0707    0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    0.3167    2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5656   -0.2295    3.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4674    0.4711    2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7066   -1.1367    2.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1504    0.9048    0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4937    0.1213   -1.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8646   -1.9487   -2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9173   -3.2343   -1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5192   -2.4867    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5417    0.4107   -1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1861    0.9526   -1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857   -2.3283   -0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2857   -2.2372   -1.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5505    0.3292    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9576    0.1504    0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 20 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
 11 42  1  0
 42 41  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 24 35  1  0
 35 36  2  0
 15 16  1  0
 41 14  1  0
 36 21  1  0
  9  4  1  0
 34 29  1  0
 17 52  1  0
 19 53  1  0
 38 65  1  0
 40 66  1  0
 13 51  1  0
 12 50  1  0
  3 43  1  0
  3 44  1  0
  5 45  1  0
  6 46  1  0
  7 47  1  0
  8 48  1  0
  9 49  1  0
 42 68  1  0
 41 67  1  0
 22 54  1  0
 23 55  1  0
 28 56  1  0
 28 57  1  0
 30 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
 36 64  1  0
M  END


  Mrv1652309022201412D          

 42 46  0  0  0  0            999 V2000
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  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
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  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
   -4.2868   -4.1250    0.0000 C   0  0  0  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
   -5.7158   -4.9500    0.0000 C   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 24 35  1  0  0  0  0
 35 36  2  0  0  0  0
 21 36  1  0  0  0  0
 20 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 15 39  1  0  0  0  0
 39 40  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  2  0  0  0  0
 11 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0144663

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C(=C(O)C(O)=C1C1=CC=C(OC(=O)CC2=CC=CC=C2)C=C1)C1=CC=C(OC(=O)CC2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H26O8/c35-27(19-21-7-3-1-4-8-21)41-25-15-11-23(12-16-25)29-31(37)33(39)30(34(40)32(29)38)24-13-17-26(18-14-24)42-28(36)20-22-9-5-2-6-10-22/h1-18,37-40H,19-20H2

> <INCHI_KEY>
CJQAGKRKLMMDBF-UHFFFAOYSA-N

> <FORMULA>
C34H26O8

> <MOLECULAR_WEIGHT>
562.574

> <EXACT_MASS>
562.162767797

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
60.80660996145107

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate

> <ALOGPS_LOGP>
6.00

> <JCHEM_LOGP>
6.936636841333332

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.751668194860805

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.407677689806404

> <JCHEM_PKA_STRONGEST_BASIC>
-6.0267436467665805

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
155.96260000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl phenylacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0     -13.337 -12.320   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0     -14.670 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -16.004 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.004 -13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -14.670 -14.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -14.670 -16.170   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -16.004 -16.940   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -17.338 -16.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11                                                       
CONECT   11   10   12   42                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   41                                                  
CONECT   15   14   16   39                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   37                                                  
CONECT   21   20   22   36                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   35                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   24   36                                                       
CONECT   36   35   21                                                       
CONECT   37   20   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   15   40                                                  
CONECT   40   39                                                            
CONECT   41   14   42                                                       
CONECT   42   41   11                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
Vialinin a	MeSH
5',6'-Bis(phenylacetoxy)-1,1'-4',1''-terphenyl-2',3',4,4''-tetraol	MeSH

Chemical Formula

C₃₄H₂₆O₈

Average Mass

562.5740 Da

Monoisotopic Mass

562.16277 Da

IUPAC Name

4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate

Traditional Name

4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl phenylacetate

CAS Registry Number

Not Available

SMILES

OC1=C(O)C(=C(O)C(O)=C1C1=CC=C(OC(=O)CC2=CC=CC=C2)C=C1)C1=CC=C(OC(=O)CC2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C34H26O8/c35-27(19-21-7-3-1-4-8-21)41-25-15-11-23(12-16-25)29-31(37)33(39)30(34(40)32(29)38)24-13-17-26(18-14-24)42-28(36)20-22-9-5-2-6-10-22/h1-18,37-40H,19-20H2

InChI Key

CJQAGKRKLMMDBF-UHFFFAOYSA-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
Thelephora aurantiotincta	LOTUS Database	35616633
Thelephora ganbajun	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-terphenyls. These are terphenyls with a structure containing the 1,4-diphenylbenzene skeleton.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Terphenyls

Direct Parent

P-terphenyls

Alternative Parents

Substituents

Para-terphenyl
Biphenyl
Phenol ester
Phenoxy compound
Phenol
Dicarboxylic acid or derivatives
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	6	ALOGPS
logP	6.94	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	155.96 m³·mol⁻¹	ChemAxon
Polarizability	60.81 Å³	ChemAxon
Number of Rings	5	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

C00035915

Chemspider ID

78435575

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101157244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hu L, Liu JK: p-Terphenyls from the basidiomycete Thelephora aurantiotincta. Z Naturforsch C J Biosci. 2003 May-Jun;58(5-6):452-4. doi: 10.1515/znc-2003-5-627. [PubMed:12872944 ]
Ngoc Quang D, Hashimoto T, Hitaka Y, Tanaka M, Nukada M, Yamamoto I, Asakawa Y: Thelephantins D-H: five p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta. Phytochemistry. 2003 Aug;63(8):919-24. doi: 10.1016/s0031-9422(03)00220-6. [PubMed:12895540 ]
Ye YQ, Koshino H, Onose J, Yoshikawa K, Abe N, Takahashi S: First total synthesis of vialinin A, a novel and extremely potent inhibitor of TNF-alpha production. Org Lett. 2007 Oct 11;9(21):4131-4. doi: 10.1021/ol701590b. Epub 2007 Sep 12. [PubMed:17850091 ]
LOTUS database [Link]

Showing NP-Card for 4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate (NP0144663)

MOL for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

3D MOL for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

3D SDF for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

3D-SDF for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

PDB for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

3D PDB for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

SMILES for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

INCHI for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

Structure for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)

3D Structure for NP0144663 (4-{2,3,5,6-tetrahydroxy-4'-[(2-phenylacetyl)oxy]-[1,1'-biphenyl]-4-yl}phenyl 2-phenylacetate)