NP-MRD: Showing NP-Card for terminolic acid (NP0329660)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 14:14:56 UTC

Updated at

2022-09-12 14:14:56 UTC

NP-MRD ID

NP0329660

Secondary Accession Numbers

None

Natural Product Identification

Common Name

terminolic acid

Description

Terminolic acid, also known as terminolate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. terminolic acid is found in Centella asiatica, Picrorhiza kurrooa, Siphoneugena densiflora, Terminalia complanata and Terminalia elliptica. terminolic acid was first documented in 2007 (PMID: 17679419). Based on a literature review a small amount of articles have been published on Terminolic acid (PMID: 31472271) (PMID: 34624680) (PMID: 26946378) (PMID: 24697659).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216142D          

 36 40  0  0  1  0            999 V2000
   -0.4733   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4895   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6882   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 29 25  1  6  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 17 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 14  1  1  0  0  0
  6 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END

     RDKit          3D

 84 88  0  0  0  0  0  0  0  0999 V2000
    5.4826    1.7452   -2.4515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5429    0.6767   -1.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2041   -0.2223   -3.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677   -0.1327   -0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3254    0.3228    0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9086    0.3739    0.9953 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0021    0.9917    2.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3759    2.0625    2.5389 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    0.4188    3.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340   -1.0313    1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -1.1496    1.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972   -0.4410    0.5740 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3188   -1.2759   -0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450    0.9162    0.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8692    1.9330    0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5621    1.8693    1.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1032    0.6392    0.4648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5895    0.5936    0.4310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2903    0.9364    1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0478    1.6253   -0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5206    1.6470   -0.7941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7648    2.1991   -2.0761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2437    0.3789   -0.5960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0784    0.3717    0.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100   -0.8657   -0.5981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1539   -1.9117    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5033   -1.4605   -2.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7767   -2.6154   -2.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984   -0.7037   -0.2185 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4483   -1.9012    0.5253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9269   -2.0812    1.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -1.7825    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3535   -0.5290    0.9693 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3680   -0.6920    2.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0566    1.2176    0.1348 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2962    1.2516   -1.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5011    2.6449   -1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5084    1.2893   -2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1876    1.9541   -3.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3702    0.1862   -3.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9918   -1.2760   -2.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1347   -0.3184   -3.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4525   -0.1083   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951   -1.2070   -0.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7230    1.3721    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9810   -0.3132    1.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    0.6533    4.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0022   -1.3867    2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7781   -1.7685    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7584   -2.2321    1.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8979   -0.7359    2.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3928   -1.3817   -0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8113   -0.9840   -1.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333   -2.3071   -0.3796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    2.9791    0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1094    2.7937    0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6795    1.8364    2.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7809    0.7742   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    0.1173    2.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639    1.2744    2.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9958    1.8181    1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5491    1.3062   -1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033    2.6297   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9680    2.4119   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6039    2.6942   -2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0065    0.2986   -1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3099    1.2764    0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1903   -1.9320   -0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7535   -2.9216    0.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2847   -1.6084    1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0736   -0.6798   -2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5769   -1.5719   -2.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1707   -3.1344   -2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3914   -0.6968   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7284   -2.7867   -0.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575   -3.0421    1.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351   -1.6933   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5437   -2.7112    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842   -0.7565    2.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0973   -1.6794    2.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1243    0.1332    3.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3028    2.2808    0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2479    2.3124   -1.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667    0.8216   -1.8226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  1
 25 27  1  0
 27 28  1  0
 25 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  1
 14 35  1  0
 35 36  1  0
  6  7  1  1
  7  9  1  0
  7  8  2  0
 36  2  1  0
 35  6  1  0
 33 12  1  0
 33 17  1  0
 29 18  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  6
 19 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  1
 22 65  1  0
 23 66  1  6
 24 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  0
 29 74  1  6
 30 75  1  6
 31 76  1  0
 32 77  1  0
 32 78  1  0
 34 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  1
 36 83  1  0
 36 84  1  0
  9 47  1  0
M  END


  Mrv1652309122216142D          

 36 40  0  0  1  0            999 V2000
   -0.4733   -3.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4895   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2520   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6882   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 29 25  1  6  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 17 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 34  1  6  0  0  0
 35 14  1  1  0  0  0
  6 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329660

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5[C@H](O)C[C@@]34C)[C@@H]2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O6/c1-25(2)9-11-30(24(35)36)12-10-28(5)17(18(30)13-25)7-8-21-26(3)14-20(33)23(34)27(4,16-31)22(26)19(32)15-29(21,28)6/h7,18-23,31-34H,8-16H2,1-6H3,(H,35,36)/t18-,19+,20+,21+,22+,23-,26+,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
IDQVFXZQPGAVAM-GGVBUJAJSA-N

> <FORMULA>
C30H48O6

> <MOLECULAR_WEIGHT>
504.708

> <EXACT_MASS>
504.345089266

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
57.55532290333199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <JCHEM_LOGP>
2.9303938726666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.530807290816668

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6448773358814535

> <JCHEM_PKA_STRONGEST_BASIC>
-2.789446682069287

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
138.35320000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.883  -6.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.831  -5.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.114  -5.803   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.804 -12.471   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   36                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10   35                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   33                                             
CONECT   13   12                                                            
CONECT   14   12   15   35                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   33                                                  
CONECT   18   17   19   20   29                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   29                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   25   18   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   17   12   34                                             
CONECT   34   33                                                            
CONECT   35   14    6   36                                                  
CONECT   36   35    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Terminolate	Generator

Chemical Formula

C₃₀H₄₈O₆

Average Mass

504.7080 Da

Monoisotopic Mass

504.34509 Da

IUPAC Name

(4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

(4aS,6aS,6bR,8R,8aR,9R,10R,11R,12aR,12bR,14bS)-8,10,11-trihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)[C@@H]5[C@H](O)C[C@@]34C)[C@@H]2C1)C(O)=O

InChI Identifier

InChI=1S/C30H48O6/c1-25(2)9-11-30(24(35)36)12-10-28(5)17(18(30)13-25)7-8-21-26(3)14-20(33)23(34)27(4,16-31)22(26)19(32)15-29(21,28)6/h7,18-23,31-34H,8-16H2,1-6H3,(H,35,36)/t18-,19+,20+,21+,22+,23-,26+,27-,28+,29+,30-/m0/s1

InChI Key

IDQVFXZQPGAVAM-GGVBUJAJSA-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
Centella asiatica	LOTUS Database	35616633
Picrorhiza kurrooa	LOTUS Database	35616633
Siphoneugena densiflora	LOTUS Database	35616633
Terminalia complanata	LOTUS Database	35616633
Terminalia elliptica	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

Substituents

Triterpenoid
12-hydroxysteroid
Hydroxysteroid
12-beta-hydroxysteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	2.93	ChemAxon
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	138.35 m³·mol⁻¹	ChemAxon
Polarizability	57.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00058138

Chemspider ID

10235831

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12314613

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Oluyemi WM, Samuel BB, Kaehlig H, Zehl M, Parapini S, D'Alessandro S, Taramelli D, Krenn L: Antiplasmodial activity of triterpenes isolated from the methanolic leaf extract of Combretum racemosum P. Beauv. J Ethnopharmacol. 2020 Jan 30;247:112203. doi: 10.1016/j.jep.2019.112203. Epub 2019 Aug 28. [PubMed:31472271 ]
Salih EYA, Julkunen-Tiitto R, Luukkanen O, Fahmi MKM, Fyhrquist P: Hydrolyzable tannins (ellagitannins), flavonoids, pentacyclic triterpenes and their glycosides in antimycobacterial extracts of the ethnopharmacologically selected Sudanese medicinal plant Combretum hartmannianum Schweinf. Biomed Pharmacother. 2021 Dec;144:112264. doi: 10.1016/j.biopha.2021.112264. Epub 2021 Oct 5. [PubMed:34624680 ]
Gossan DP, Alabdul Magid A, Yao-Kouassi PA, Josse J, Gangloff SC, Morjani H, Voutquenne-Nazabadioko L: Antibacterial and cytotoxic triterpenoids from the roots of Combretum racemosum. Fitoterapia. 2016 Apr;110:89-95. doi: 10.1016/j.fitote.2016.03.002. Epub 2016 Mar 2. [PubMed:26946378 ]
Yang GX, Zhang RZ, Lou B, Cheng KJ, Xiong J, Hu JF: Chemical constituents from Melastoma dodecandrum and their inhibitory activity on interleukin-8 production in HT-29 cells. Nat Prod Res. 2014;28(17):1383-7. doi: 10.1080/14786419.2014.903480. Epub 2014 Apr 4. [PubMed:24697659 ]
Pan J, Kai G, Yuan C, Zhou B, Jin R, Yuan Y: [Separation and determination of madecassic acid in triterpenic genins of Centella asiatica by high performance liquid chromatography using beta-cyclodextrin as mobile phase additive]. Se Pu. 2007 May;25(3):316-8. doi: 10.1016/s1872-2059(07)60009-1. [PubMed:17679419 ]
LOTUS database [Link]

Showing NP-Card for terminolic acid (NP0329660)

MOL for NP0329660 (terminolic acid)

3D MOL for NP0329660 (terminolic acid)

3D SDF for NP0329660 (terminolic acid)

3D-SDF for NP0329660 (terminolic acid)

PDB for NP0329660 (terminolic acid)

3D PDB for NP0329660 (terminolic acid)

SMILES for NP0329660 (terminolic acid)

INCHI for NP0329660 (terminolic acid)

Structure for NP0329660 (terminolic acid)

3D Structure for NP0329660 (terminolic acid)