NP-MRD: Showing NP-Card for (1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid (NP0254596)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-07 18:48:39 UTC

Updated at

2022-09-07 18:48:39 UTC

NP-MRD ID

NP0254596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid

Description

(1R,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid is found in Uncaria elliptica. It was first documented in 2002 (PMID: 35412727). Based on a literature review a significant number of articles have been published on (1R,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid (PMID: 27466641) (PMID: 36099392) (PMID: 31661213) (PMID: 31593386) (PMID: 29589881) (PMID: 29337482).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072220482D          

 35 39  0  0  1  0            999 V2000
   -0.1105   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  2  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
    1.1270   -6.6809    0.0000 O   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
    1.5395   -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  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  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  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
    5.9337   -6.0644    0.0000 C   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  0  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  1  0  0  0  0  0  0  0  0  0
    1.8266   -3.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -2.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  6  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 23 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 13  1  1  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  1  0  0  0
M  END

     RDKit          3D

 79 83  0  0  0  0  0  0  0  0999 V2000
   -5.7014    2.5562    0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9073    1.6569   -0.2230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5889    0.4070   -0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0204   -0.8838   -0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5632   -1.0739   -0.3100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2493   -1.8418   -1.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5412   -1.3329   -2.4407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7182   -3.1358   -1.7501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8694   -1.7994    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4040   -1.9981    0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6613   -0.6738    0.4610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6509   -0.2220    1.9109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302    0.1936   -0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    0.9250   -1.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    1.0300   -1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311    0.3768   -0.4540 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9091    0.2382   -0.8171 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1958   -0.5204   -2.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    1.7023   -1.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807    1.9047   -1.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5521    1.2305   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5593    1.7549    0.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1206   -0.0834    0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795   -0.0768    1.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8528   -1.1755   -0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451   -0.1141    0.4086 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0247   -1.3071    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6718   -2.3011    1.1736 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6038   -1.1643    1.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7887   -0.7986    0.1127 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9432   -2.0884   -0.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075    0.2888   -0.4572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5766    1.2331    0.4528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7684    2.4296    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1554    0.6250    1.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7764    2.3805    0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2384    2.5288    1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5562    3.6224    0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5616    2.2267   -1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6472    0.4566   -0.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7039    0.3810   -1.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5188   -1.6758   -0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4072   -1.1889    0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4860   -3.3731   -2.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3061   -2.8459    0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0721   -1.4239    1.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0258   -2.6924    1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3878   -2.5231   -0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2630   -1.0917    2.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1218    0.7229    2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6474   -0.0741    2.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480    1.5664   -1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8763    2.1384   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9692    0.6708   -2.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4915    1.1306    0.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2544   -0.8400   -2.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7162    0.0816   -2.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8738   -1.3923   -1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8354    2.3866   -0.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9358    1.8806   -2.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080    1.5839   -2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9672    2.9923   -1.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5686   -1.0771    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6088    0.3322    1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9248    0.6509    2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1175   -0.8101   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4245   -2.1685   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8800   -1.3090    0.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3750    0.7293    1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -2.1518    1.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5732   -0.3450    2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4138   -2.0861   -1.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0276   -2.3914   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -2.8956   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683    0.5646   -1.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4850    2.3633    1.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4102    3.3362    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607    2.5023    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8513    1.1656    2.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  6
 13 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  1
  5  6  1  6
  6  8  1  0
  6  7  2  0
 33  2  1  0
 32  5  1  0
 30 11  1  0
 30 16  1  0
 26 17  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  6
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  0
 10 48  1  0
 12 49  1  0
 12 50  1  0
 12 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  1
 18 56  1  0
 18 57  1  0
 18 58  1  0
 19 59  1  0
 19 60  1  0
 20 61  1  0
 20 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  1
 29 70  1  0
 29 71  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
 32 75  1  6
 34 76  1  0
 34 77  1  0
 34 78  1  0
 35 79  1  0
  8 44  1  0
M  END


  Mrv1652309072220482D          

 35 39  0  0  1  0            999 V2000
   -0.1105   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  2  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
    1.1270   -6.6809    0.0000 O   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
    1.5395   -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  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  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  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
    5.9337   -6.0644    0.0000 C   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  0  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  1  0  0  0  0  0  0  0  0  0
    1.8266   -3.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1558   -2.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  6  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 23 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  6  0  0  0
 32 13  1  1  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0254596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5C(=O)C[C@@]34C)[C@@H]2[C@]1(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-20-26(4)12-11-21(32)25(2,3)23(26)19(31)16-28(20,27)6/h8,17,20,22-23,35H,9-16H2,1-7H3,(H,33,34)/t17-,20-,22-,23+,26-,27-,28-,29-,30+/m1/s1

> <INCHI_KEY>
NZLFSRQUNSCSDS-XTSCOJJISA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.677

> <EXACT_MASS>
484.318874517

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.88502097646028

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-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>
4.984829077

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.485546569319816

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.488588859837257

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0362747258490863

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
135.14809999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.206  -5.803   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      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.804 -12.471   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.410  -6.320   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.157  -5.597   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9   32                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   30                                             
CONECT   12   11                                                            
CONECT   13   11   14   32                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18   19   26                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   17   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   16   11   31                                             
CONECT   31   30                                                            
CONECT   32   13    5   33                                                  
CONECT   33   32    2   34   35                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,4AS,6as,6BR,8ar,12ar,12BR,14BS)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate	Generator

Chemical Formula

C₃₀H₄₄O₅

Average Mass

484.6770 Da

Monoisotopic Mass

484.31887 Da

IUPAC Name

(1R,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-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

(1R,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5C(=O)C[C@@]34C)[C@@H]2[C@]1(C)O)C(O)=O

InChI Identifier

InChI=1S/C30H44O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-20-26(4)12-11-21(32)25(2,3)23(26)19(31)16-28(20,27)6/h8,17,20,22-23,35H,9-16H2,1-7H3,(H,33,34)/t17-,20-,22-,23+,26-,27-,28-,29-,30+/m1/s1

InChI Key

NZLFSRQUNSCSDS-XTSCOJJISA-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
Uncaria 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
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.98	ChemAxon
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	135.15 m³·mol⁻¹	ChemAxon
Polarizability	54.89 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

15226720

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Freebody J: "The Root of All Evil is Inactivity": The Response of French Psychiatrists to New Approaches to Patient Work and Occupation, 1918-1939. 2021. [PubMed:36099392 ]
Authors unspecified: Childhood Pulmonary Inflammatory Myofibroblastic Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:35412727 ]
Authors unspecified: Childhood Adrenocortical Carcinoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31661213 ]
Authors unspecified: Childhood Breast Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:31593386 ]
Authors unspecified: Cognitive Impairment in Adults with Non-Central Nervous System Cancers (PDQ(R)): Patient Version. 2002. [PubMed:29589881 ]
Authors unspecified: Childhood Oral Cavity Cancer Treatment (PDQ(R)): Health Professional Version.. 2002. [PubMed:29337482 ]
Authors unspecified: Childhood Oral Cavity Cancer Treatment (PDQ(R)): Patient Version.. 2002. [PubMed:29337481 ]
Authors unspecified: Childhood Laryngeal Tumors Treatment (PDQ(R)): Patient Version.. 2002. [PubMed:29337476 ]
Authors unspecified: Chronic Lymphocytic Leukemia Treatment (PDQ(R)): Patient Version.. 2002. [PubMed:26389485 ]
Authors unspecified: Fatigue (PDQ(R)): Health Professional Version.. 2002. [PubMed:26389484 ]
Authors unspecified: Chronic Lymphocytic Leukemia Treatment (PDQ(R)): Health Professional Version.. 2002. [PubMed:26389470 ]
Authors unspecified: Last Days of Life (PDQ(R)): Patient Version.. 2002. [PubMed:26389429 ]
Authors unspecified: Small Intestine Cancer Treatment (PDQ(R)): Health Professional Version.. 2002. [PubMed:26389423 ]
Authors unspecified: Childhood Medulloblastoma and Other Central Nervous System Embryonal Tumors Treatment (PDQ(R)): Health Professional Version.. 2002. [PubMed:26389418 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid (NP0254596)

MOL for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

3D MOL for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

3D SDF for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

3D-SDF for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

PDB for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

3D PDB for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

SMILES for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

INCHI for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

Structure for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)

3D Structure for NP0254596 ((1r,2r,4as,6as,6br,8ar,12ar,12br,14bs)-1-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-8,10-dioxo-2,3,4,5,6,7,8a,11,12,12b,13,14b-dodecahydropicene-4a-carboxylic acid)