NP-MRD: Showing NP-Card for bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid (NP0303311)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 17:33:53 UTC

Updated at

2022-09-10 17:33:54 UTC

NP-MRD ID

NP0303311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid

Description

2,2-Bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid is found in Carthamus tinctorius. 2,2-Bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521552D          

 68 73  0  0  0  0            999 V2000
   -3.2040   -3.3265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -3.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -4.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -4.9765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -5.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -6.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -7.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2040   -5.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9185   -6.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2040   -4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9185   -4.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -6.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909   -6.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784   -5.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340   -5.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162   -4.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287   -4.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590   -5.0089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4108   -3.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141   -3.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681   -3.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -2.9697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -2.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2522   -2.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444   -1.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141   -1.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963   -0.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340    0.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    1.1087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3087   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909    0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515   -0.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0872   -2.1945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -2.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -3.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -3.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515   -4.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996   -2.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7121   -3.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2424   -2.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0549   -2.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5852   -1.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030   -1.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8333   -0.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4905   -1.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9602   -1.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266   -4.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3087   -4.8067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8050   -1.9923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5643   -5.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768   -5.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -6.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -6.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -7.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -7.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249   -7.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552   -7.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9677   -7.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -6.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0623   -6.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926   -7.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051   -7.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3105   -8.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980   -8.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789   -5.2391    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 40 38  1  4  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 42 48  1  0  0  0  0
 37 49  1  0  0  0  0
 20 49  1  0  0  0  0
 49 50  2  0  0  0  0
 36 51  1  0  0  0  0
 15 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
 54 55  2  0  0  0  0
 12 55  1  0  0  0  0
 55 56  1  0  0  0  0
 54 57  1  0  0  0  0
 57 58  2  0  0  0  0
 59 57  1  4  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 63 64  2  0  0  0  0
 64 65  1  0  0  0  0
 64 66  1  0  0  0  0
 66 67  2  0  0  0  0
 61 67  1  0  0  0  0
 14 68  1  0  0  0  0
M  END

     RDKit          3D

112117  0  0  0  0  0  0  0  0999 V2000
   -2.4209    2.1975   -1.1232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717    1.4683   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4343    2.0945   -0.0034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8978    3.2845   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5673    4.5659   -0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6997    4.7845   -1.6058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3436    6.0738   -2.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8611    7.1840   -1.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552    8.4764   -1.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7438    6.9587   -0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0985    5.7112    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708    0.0696   -0.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617   -0.8369    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7687   -0.5697    0.7572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1966   -2.2999    0.2323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2282   -2.9435   -0.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2780   -2.7178    1.6929 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5179   -2.3163    2.1795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4519   -3.3071    2.2714 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7600   -2.6817    2.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7595   -3.6659    2.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9987   -4.2404    3.3742 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0335   -3.5143    4.5659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6253   -4.7738    3.1128 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7560   -6.1529    2.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150   -4.1158    1.9699 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5478   -4.3283    2.1672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427   -2.6344   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641   -3.9616   -0.4333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.7725   -1.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054   -2.0434   -1.7207 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4463   -3.4348   -1.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -3.9598   -3.1656 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745   -4.3085   -1.0100 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055   -1.3695   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -0.8807    0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077   -1.0036    0.8504 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5486   -0.2330    0.6152 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8681   -1.0005    1.7849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    1.1800    1.1005 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0741    1.1218    1.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7202    2.3037    2.4445 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4562    3.4450    1.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1116    4.5491    2.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7213    2.7128    3.5169 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1454    2.7897    4.7809 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8026    1.6499    3.5274 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3790    0.4139    3.9232 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    1.5867    2.0818 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8209    2.8953    1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6947   -0.2005   -0.3109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8934    0.4160    0.1703 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7155   -0.6721   -1.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8502   -0.6547   -2.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621   -1.1141   -3.6172 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1601   -0.1914   -2.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2471   -0.0206   -2.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6036   -0.2085   -4.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7972   -0.2730   -5.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2273   -0.5613   -6.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5714   -0.7874   -6.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0559   -1.0739   -8.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4375   -0.7287   -5.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9800   -0.4484   -4.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4545   -1.3083   -2.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218   -1.7806   -3.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983   -0.3620   -1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8944    0.4937   -1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1261    1.3889    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9428    3.3628    0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2606    4.0090   -2.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6482    6.2249   -2.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078    9.0307   -1.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1774    7.8218    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8146    5.6140    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6546   -0.9408    0.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2142   -2.6237   -1.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5471   -2.0621    2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6666   -3.8218    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6533   -2.1239    3.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1606   -1.9463    1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1759   -3.8629    1.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7586   -5.0416    3.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6666   -3.8818    5.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535   -4.6916    4.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7024   -6.3708    2.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1620   -4.7408    1.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250   -3.6589    2.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576   -4.6496   -1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652   -1.5444   -2.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879   -4.1943   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907   -0.5117    1.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0896   -1.5422    2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2314    1.8380    0.2384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2362    2.1081    2.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3019    3.7483    0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339    3.2634    0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9182    5.0982    2.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1969    3.6854    3.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112    2.5008    5.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6581    1.9845    4.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9064    0.0709    4.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1887    0.8872    2.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7535    3.0050    2.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9164    1.4242   -0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3193    0.0304   -1.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0970    0.4023   -2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7575   -0.0387   -5.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5241   -0.6018   -7.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3513   -0.3175   -8.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5111   -0.9006   -5.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6807   -0.4055   -3.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 17 15  1  0
 15 16  1  6
 15 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  1  0
 32 34  1  0
 32 33  2  0
 31 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  1  1
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 42 45  1  0
 45 46  1  0
 45 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 38 51  1  0
 51 52  1  0
 51 53  2  0
 53 54  1  0
 54 55  2  0
 54 56  1  0
 56 57  2  0
 57 58  1  0
 58 59  2  0
 59 60  1  0
 60 61  2  0
 61 62  1  0
 61 63  1  0
 63 64  2  0
 53 65  1  0
 65 66  2  0
 30 67  1  0
 67 68  2  0
 67 12  1  0
 12  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 12 13  2  0
 13 14  1  0
 22 19  1  0
 13 15  1  0
 65 35  1  0
 11  5  1  0
 49 40  1  0
 64 58  1  0
 21 82  1  0
 20 80  1  0
 20 81  1  0
 19 79  1  6
 17 78  1  1
 26 87  1  6
 27 88  1  0
 24 85  1  1
 25 86  1  0
 22 83  1  1
 23 84  1  0
 16 77  1  0
 29 89  1  0
 31 90  1  6
 34 91  1  0
 37 92  1  0
 39 93  1  0
 40 94  1  6
 42 95  1  1
 43 96  1  0
 43 97  1  0
 44 98  1  0
 45 99  1  6
 46100  1  0
 47101  1  1
 48102  1  0
 49103  1  1
 50104  1  0
 52105  1  0
 56106  1  0
 57107  1  0
 59108  1  0
 60109  1  0
 62110  1  0
 63111  1  0
 64112  1  0
  3 69  1  0
  4 70  1  0
  6 71  1  0
  7 72  1  0
  9 73  1  0
 10 74  1  0
 11 75  1  0
 14 76  1  0
M  END


  Mrv1533004161521552D          

 68 73  0  0  0  0            999 V2000
   -3.2040   -3.3265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -3.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -4.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -4.9765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -5.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -6.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4895   -7.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2040   -5.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9185   -6.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2040   -4.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9185   -4.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -6.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909   -6.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784   -5.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340   -5.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162   -4.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287   -4.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590   -5.0089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4108   -3.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141   -3.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681   -3.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8805   -2.9697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -2.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2522   -2.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444   -1.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2141   -1.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963   -0.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340    0.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    1.1087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3087   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909    0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -0.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515   -0.6440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0872   -2.1945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -2.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5569   -3.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693   -3.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515   -4.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996   -2.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7121   -3.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2424   -2.4221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0549   -2.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5852   -1.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3030   -1.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8333   -0.5261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4905   -1.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9602   -1.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266   -4.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3087   -4.8067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8050   -1.9923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5643   -5.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3768   -5.7842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -6.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -6.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -7.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125   -7.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249   -7.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1552   -7.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9677   -7.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -6.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0623   -6.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5926   -7.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4051   -7.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3105   -8.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980   -8.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789   -5.2391    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 40 38  1  4  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 42 48  1  0  0  0  0
 37 49  1  0  0  0  0
 20 49  1  0  0  0  0
 49 50  2  0  0  0  0
 36 51  1  0  0  0  0
 15 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
 54 55  2  0  0  0  0
 12 55  1  0  0  0  0
 55 56  1  0  0  0  0
 54 57  1  0  0  0  0
 57 58  2  0  0  0  0
 59 57  1  4  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 63 64  2  0  0  0  0
 64 65  1  0  0  0  0
 64 66  1  0  0  0  0
 66 67  2  0  0  0  0
 61 67  1  0  0  0  0
 14 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(C(O)C(O)C1O)C1(O)C(O)=C(C(C(O)=O)C2=C(O)C(O)(C3OC(CO)C(O)C(O)C3O)C(O)=C(C(=O)C=CC3=CC=C(O)C=C3)C2=O)C(=O)C(C(=O)C=CC2=CC=C(O)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C44H44O24/c45-13-21-28(51)32(55)34(57)40(67-21)43(65)36(59)23(19(49)11-5-15-1-7-17(47)8-2-15)30(53)26(38(43)61)25(42(63)64)27-31(54)24(20(50)12-6-16-3-9-18(48)10-4-16)37(60)44(66,39(27)62)41-35(58)33(56)29(52)22(14-46)68-41/h1-12,21-22,25,28-29,32-35,40-41,45-48,51-52,55-62,65-66H,13-14H2,(H,63,64)

> <INCHI_KEY>
UVYRSIWRPCSELS-UHFFFAOYSA-N

> <FORMULA>
C44H44O24

> <MOLECULAR_WEIGHT>
956.812

> <EXACT_MASS>
956.222252297

> <JCHEM_ACCEPTOR_COUNT>
24

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
88.66370349772524

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
17

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-4.327099742333333

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.1563028320914217

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.46228756145129424

> <JCHEM_PKA_STRONGEST_BASIC>
-6.752958022614634

> <JCHEM_POLAR_SURFACE_AREA>
447.72

> <JCHEM_REFRACTIVITY>
228.72469999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      -5.981  -6.209   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.772  -7.158   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.647  -8.519   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.313  -9.289   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.313 -10.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.647 -11.599   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.647 -13.139   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.981 -10.829   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.315 -11.599   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.981  -9.289   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -7.315  -8.519   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.980 -11.599   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.970 -12.779   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.453 -10.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.064  -9.885   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.590  -8.438   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.107  -8.170   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.097  -9.350   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.634  -6.723   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.400  -7.258   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.127  -5.811   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.644  -5.543   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.863  -4.631   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.471  -3.861   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.390  -3.184   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.400  -2.004   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.926  -0.557   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.064   0.622   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.463   2.070   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.443  -0.290   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.970   1.157   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.433  -1.470   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.949  -1.202   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.906  -2.917   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.896  -4.096   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.379  -4.899   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.906  -6.346   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.423  -6.613   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.949  -8.060   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -5.413  -5.433   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.929  -5.701   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -7.919  -4.521   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -9.436  -4.789   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -10.426  -3.609   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -9.899  -2.162   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -10.889  -0.982   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -8.382  -1.894   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -7.392  -3.074   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -1.916  -7.525   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -2.443  -8.973   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -3.369  -3.719   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       1.053 -11.065   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       2.570 -10.797   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       0.527 -12.512   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -0.990 -12.779   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -1.517 -14.226   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       1.517 -13.691   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       0.990 -15.139   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       3.033 -13.424   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       4.023 -14.604   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       5.540 -14.336   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       6.066 -12.889   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       7.583 -12.622   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       8.573 -13.801   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      10.090 -13.534   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       8.046 -15.249   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       6.530 -15.516   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      -2.947  -9.780   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   14   55                                             
CONECT   13   12                                                            
CONECT   14   12   15   68                                                  
CONECT   15   14   16   52                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21   49                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   36                                             
CONECT   24   23                                                            
CONECT   25   23   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   25   35                                                  
CONECT   35   34                                                            
CONECT   36   23   37   51                                                  
CONECT   37   36   38   49                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   48                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   42                                                       
CONECT   49   37   20   50                                                  
CONECT   50   49                                                            
CONECT   51   36                                                            
CONECT   52   15   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   57                                                  
CONECT   55   54   12   56                                                  
CONECT   56   55                                                            
CONECT   57   54   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   67                                                  
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64   67                                                       
CONECT   67   66   61                                                       
CONECT   68   14                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  146    0
END

View in JSmol

Synonyms

Value	Source
2,2-Bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetate	Generator

Chemical Formula

C₄₄H₄₄O₂₄

Average Mass

956.8120 Da

Monoisotopic Mass

956.22225 Da

IUPAC Name

2,2-bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid

Traditional Name

bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid

CAS Registry Number

Not Available

SMILES

OCC1OC(C(O)C(O)C1O)C1(O)C(O)=C(C(C(O)=O)C2=C(O)C(O)(C3OC(CO)C(O)C(O)C3O)C(O)=C(C(=O)C=CC3=CC=C(O)C=C3)C2=O)C(=O)C(C(=O)C=CC2=CC=C(O)C=C2)=C1O

InChI Identifier

InChI=1S/C44H44O24/c45-13-21-28(51)32(55)34(57)40(67-21)43(65)36(59)23(19(49)11-5-15-1-7-17(47)8-2-15)30(53)26(38(43)61)25(42(63)64)27-31(54)24(20(50)12-6-16-3-9-18(48)10-4-16)37(60)44(66,39(27)62)41-35(58)33(56)29(52)22(14-46)68-41/h1-12,21-22,25,28-29,32-35,40-41,45-48,51-52,55-62,65-66H,13-14H2,(H,63,64)

InChI Key

UVYRSIWRPCSELS-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
Carthamus tinctorius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Oligosaccharide
Steroid
Glycosyl compound
O-glycosyl compound
Oxane
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Polyol
Organic oxygen compound
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.41	ALOGPS
logP	-4.3	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	0.46	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	17	ChemAxon
Polar Surface Area	447.72 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	228.72 m³·mol⁻¹	ChemAxon
Polarizability	88.66 Å³	ChemAxon
Number of Rings	6	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid (NP0303311)

MOL for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

3D MOL for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

3D SDF for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

3D-SDF for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

PDB for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

3D PDB for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

SMILES for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

INCHI for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

Structure for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)

3D Structure for NP0303311 (bis({2,3,4-trihydroxy-5-[3-(4-hydroxyphenyl)prop-2-enoyl]-6-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]cyclohexa-1,4-dien-1-yl})acetic acid)