NP-MRD: Showing NP-Card for 16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid (NP0244866)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 05:45:23 UTC

Updated at

2022-09-07 05:45:23 UTC

NP-MRD ID

NP0244866

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid

Description

3-O-Protocatechuoylceanothic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-O-Protocatechuoylceanothic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-O-protocatechuoylceanothic acid has been detected, but not quantified in, fruits. 16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid is found in Ziziphus jujuba. This could make 3-O-protocatechuoylceanothic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241207462D          

 45 50  0  0  0  0            999 V2000
    1.1164   -0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8328    0.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507    0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602    0.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4390    1.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2598    1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5912    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793    0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793   -0.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602   -0.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507   -0.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507   -1.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1474    3.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    2.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0818    2.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    0.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4014   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4014   -1.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -1.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219   -1.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8328   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0577   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904   -1.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4466    0.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    1.0148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904   -0.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8717   -1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967   -1.0573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4122    0.6930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8112   -0.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1093   -1.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967   -2.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9371   -1.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3482   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1787   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5940   -1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1787   -1.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3482   -1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5940   -3.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4122   -1.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454   -1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  1 22  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
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 33  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 22  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 29  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 45  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 30  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 35  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 42  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 43  1  0  0  0  0
 40 41  1  0  0  0  0
 40 44  1  0  0  0  0
 41 42  2  0  0  0  0
M  END

     RDKit          3D

 95100  0  0  0  0  0  0  0  0999 V2000
   -5.3629    2.4443    1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4662    2.3653   -0.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0282    3.5458   -0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0696    1.2189   -0.9730 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3951    0.6046   -1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3117   -0.8908   -1.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7800   -1.0677   -1.1760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4161   -1.0150   -2.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7795   -1.9801   -3.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7077    0.0258   -3.4463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533   -2.3500   -0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8630   -2.2149   -0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6506   -1.1709    0.7807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4374   -1.5210    1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0487    0.1675    0.1777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1023    0.6602   -0.8389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7239    0.1923   -0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3223   -0.9765   -0.0117 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1685   -0.9716    0.3035 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5674   -2.4563    0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0208   -0.3552   -0.7613 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9247   -1.2907   -1.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7318   -1.5376   -2.6872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987   -1.9286   -0.8728 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9261    0.6835   -0.1402 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3058    0.3248   -0.2413 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2552    1.1183   -0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8578    2.2121   -1.3291 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6679    0.7504   -0.9503 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1604   -0.4153   -0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5035   -0.7173   -0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4013    0.1515   -1.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7438   -0.1849   -1.3137 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9033    1.3292   -1.7119 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7604    2.2164   -2.3463 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5507    1.6041   -1.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4937    0.8235    1.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7634    0.7398    2.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698    2.2150    1.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270   -0.2863    1.5629 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4555    0.1653    2.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285    0.2531    1.9348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1984   -1.0448    1.1851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9226   -2.1378    2.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4555    0.0690   -0.2907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9953    1.7180    1.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6951    3.3868    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4557    3.6633   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9908    4.4682   -0.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1066    3.3166   -1.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849    1.6524   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2232    0.9799   -0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6373    0.8572   -2.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6280   -1.1223   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7960   -1.4992   -1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2884   -0.0655   -4.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9448   -2.7152    0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4117   -3.1392   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4472   -1.7894   -1.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4093   -3.1883   -0.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2620   -0.8503    2.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5396   -1.5306    1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060   -2.6026    2.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0299    0.8541    1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995    0.5096   -1.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295    1.7973   -0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718   -0.0896   -1.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    1.0366   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5230   -1.8987   -0.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083   -2.8181   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728   -3.1161    0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034   -2.6441    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4719    0.1771   -1.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3441   -2.8198   -1.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8179    1.6874   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4628   -1.0863    0.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8967   -1.6319   -0.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4435    0.3760   -1.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7300    2.1108   -2.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2078    2.5428   -1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3283    1.6633    1.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291    0.6683    3.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3101   -0.1862    1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6299    2.8849    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1901    2.5732    2.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    2.4106    1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1527   -1.0178    2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4123   -0.3768    3.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7051    1.2201    2.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527    1.1481    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6211    0.3596    2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -2.1625    2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5311   -1.8720    3.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2944   -3.1392    1.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0902   -0.0679    0.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  1
 40 37  1  0
 37 38  1  0
 37 39  1  0
 37 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 36  2  0
 36 34  1  0
 34 35  1  0
 34 32  2  0
 32 33  1  0
 32 31  1  0
 31 30  2  0
 25 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 15 45  1  0
  7  8  1  6
  8 10  1  0
  8  9  2  0
 45  4  1  0
 45  7  1  0
 43 13  1  0
 30 29  1  0
 43 18  1  0
 21 19  1  0
  3 48  1  0
  3 49  1  0
  3 50  1  0
  1 46  1  0
  1 47  1  0
  4 51  1  6
  5 52  1  0
  5 53  1  0
  6 54  1  0
  6 55  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  0
 12 60  1  0
 14 61  1  0
 14 62  1  0
 14 63  1  0
 15 64  1  1
 16 65  1  0
 16 66  1  0
 17 67  1  0
 17 68  1  0
 18 69  1  6
 20 70  1  0
 20 71  1  0
 20 72  1  0
 40 87  1  1
 41 88  1  0
 41 89  1  0
 42 90  1  0
 42 91  1  0
 44 92  1  0
 44 93  1  0
 44 94  1  0
 38 81  1  0
 38 82  1  0
 38 83  1  0
 39 84  1  0
 39 85  1  0
 39 86  1  0
 25 75  1  6
 36 80  1  0
 35 79  1  0
 33 78  1  0
 31 77  1  0
 30 76  1  0
 21 73  1  6
 24 74  1  0
 45 95  1  1
 10 56  1  0
M  END


  Mrv0541 02241207462D          

 45 50  0  0  0  0            999 V2000
    1.1164   -0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8328    0.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507    0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602    0.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4390    1.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2598    1.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5912    1.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793    0.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793   -0.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602   -0.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507   -0.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5507   -1.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1474    3.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8890    2.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0818    2.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    0.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4014   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4014   -1.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -1.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219   -1.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8328   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0577   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904   -1.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054   -2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4466    0.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0948    1.0148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904   -0.3932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8717   -1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967   -1.0573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4122    0.6930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7287    0.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8112   -0.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1093   -1.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6967   -2.4833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9371   -1.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3482   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1787   -2.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5940   -1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1787   -1.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3482   -1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5940   -3.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4122   -1.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454   -1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  1 22  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
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 33  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 22  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 29  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 45  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 30  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 35  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 42  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 43  1  0  0  0  0
 40 41  1  0  0  0  0
 40 44  1  0  0  0  0
 41 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0244866

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)C(CCC34C)C(C)(C)C(OC(=O)C3=CC(O)=C(O)C=C3)C5C(O)=O)C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H50O8/c1-19(2)21-12-15-37(32(43)44)17-16-34(5)22(27(21)37)9-11-26-35(34,6)14-13-25-33(3,4)29(28(30(40)41)36(25,26)7)45-31(42)20-8-10-23(38)24(39)18-20/h8,10,18,21-22,25-29,38-39H,1,9,11-17H2,2-7H3,(H,40,41)(H,43,44)

> <INCHI_KEY>
FGJNOXMHWXEMHU-UHFFFAOYSA-N

> <FORMULA>
C37H50O8

> <MOLECULAR_WEIGHT>
622.7881

> <EXACT_MASS>
622.350568576

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
68.59372413205324

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid

> <ALOGPS_LOGP>
5.30

> <JCHEM_LOGP>
7.461991593666667

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.771732222655676

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9517545617116876

> <JCHEM_PKA_STRONGEST_BASIC>
-5.841573312273437

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
167.89419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.084  -0.452   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.084   1.088   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.421   1.858   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.761   1.088   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.086   1.858   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.419   3.347   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.952   3.501   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.570   2.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.428   1.088   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.428  -0.475   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.086  -1.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.761  -0.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.761  -2.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.875   5.957   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.393   4.494   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.886   4.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.590   0.316   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.749  -1.224   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.749  -2.757   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.084  -3.521   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.401  -2.757   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.421  -1.224   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.108  -4.635   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.729  -3.224   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.063  -3.994   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.700   1.024   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.189   0.731   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.177   1.894   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.729  -0.734   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.627  -1.974   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.167  -1.974   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      10.103   1.294   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.827   0.434   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.981  -1.098   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.937  -3.306   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.167  -4.635   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -5.483  -3.306   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -6.250  -4.635   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.800  -4.635   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -8.575  -3.288   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -7.800  -1.945   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -6.250  -1.974   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -8.575  -5.957   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -10.103  -3.288   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.191  -2.559   0.000  0.00  0.00           C+0
CONECT    1    2   18   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    5    8   10   33                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    4   11   13   22                                             
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    6   14   16                                                  
CONECT   16   15                                                            
CONECT   17   18                                                            
CONECT   18    1   17   19   29                                             
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22    1   12   21   45                                             
CONECT   23   24                                                            
CONECT   24   19   23   25   30                                             
CONECT   25   24                                                            
CONECT   26   27                                                            
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   18   27   30                                                  
CONECT   30   24   29   31                                                  
CONECT   31   30   35                                                       
CONECT   32   33                                                            
CONECT   33    9   32   34                                                  
CONECT   34   33                                                            
CONECT   35   31   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   43                                                  
CONECT   40   39   41   44                                                  
CONECT   41   40   42                                                       
CONECT   42   37   41                                                       
CONECT   43   39                                                            
CONECT   44   40                                                            
CONECT   45   22                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
3-O-Protocatechuoylceanothate	Generator
16-(3,4-Dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylate	Generator

Chemical Formula

C₃₇H₅₀O₈

Average Mass

622.7881 Da

Monoisotopic Mass

622.35057 Da

IUPAC Name

16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid

Traditional Name

16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)C(CCC34C)C(C)(C)C(OC(=O)C3=CC(O)=C(O)C=C3)C5C(O)=O)C12)C(O)=O

InChI Identifier

InChI=1S/C37H50O8/c1-19(2)21-12-15-37(32(43)44)17-16-34(5)22(27(21)37)9-11-26-35(34,6)14-13-25-33(3,4)29(28(30(40)41)36(25,26)7)45-31(42)20-8-10-23(38)24(39)18-20/h8,10,18,21-22,25-29,38-39H,1,9,11-17H2,2-7H3,(H,40,41)(H,43,44)

InChI Key

FGJNOXMHWXEMHU-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
Ziziphus jujuba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homopolycyclic 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	5.3	ALOGPS
logP	7.46	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	167.89 m³·mol⁻¹	ChemAxon
Polarizability	68.59 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

HMDB0029625

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000795

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

85245649

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid (NP0244866)

MOL for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

3D MOL for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

3D SDF for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

3D-SDF for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

PDB for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

3D PDB for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

SMILES for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

INCHI for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

Structure for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)

3D Structure for NP0244866 (16-(3,4-dihydroxybenzoyloxy)-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5,15-dicarboxylic acid)