NP-MRD: Showing NP-Card for 3-Epikatonic acid (NP0023969)

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Record Information

Version

2.0

Created at

2021-04-21 17:21:37 UTC

Updated at

2021-07-26 15:24:10 UTC

NP-MRD ID

NP0023969

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Epikatonic acid

Provided By

JEOL Database JEOL Logo

Description

3-Epikatonic acid, also known as 3-epikatonate, belongs to the class of organic compounds known as pentacyclic triterpenoids. These are terpene molecules containing six isoprene units. In higher plants, the biosynthesis of terpenoids proceeds via two independent pathways localized indifferent cellular compartments. The mevalonate (MVA) pathway in the cytoplasm is responsible for the biosynthesis of sesquiterpenes and triterpenes such as 3-epikatonic acid. In the cytoplasm-localized MVA pathway, three molecules of acetyl-coenzyme A are used to produce MVA. Two ATP react with MVA to produce mevalonate diphosphate, followed by decarboxylation and dehydration with the involvement of a third molecule of ATP to give isopentenyl pyrophosphate(IPP). IPP is isomerized to the other isoprene unit, dimethylallyl pyrophosphate (DMAPP), byisopentenyl-diphosphate-D-isomerase (EC 5.3.3.2). IPP and DMAPP are active hemiterpeneintermediates (C5) in the pathways leading to more complicated terpenoids. DMAPP can produce the fundamental sesquiterpene precursor farnesyl diphosphate (FPP), with the successive addition of two further IPPs. Two molecules of FPP are joined tail-to-tail to yield theprecursor of triterpenes, squalene (C30), from which other triterpenes arise (PMID: 17250858 ).3-Epikatonic acid was first isolated from the plant Cyamopsis tetragonoloba, which is also known as guar or cluster bean (https://Doi.Org/10.1002/Mrc.1009). Cyamopsis tetragonoloba is anannual legume and the source of guar gum. Later it was isolated from Tripterygium wilfordii, Trypterygium hypolaucum and then Austroplenckia populnea. 3-Epikatonic acid has been shown to have antimalarial and anti-trypanosome activity (T. (S.) Cruzi) (PMID: 12048549 ).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306102103383D          

 81 85  0  0  0  0            999 V2000
    1.2457    4.0513    4.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442    2.5439    4.6200 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9413    2.4430    5.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    1.8408    5.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3831    2.5784    6.7814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517    1.6372    4.9514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7883    0.8936    3.6193 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1615    1.5426    2.5668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5041    2.8580    2.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613    1.7743    3.2479 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5888    2.2941    2.2216 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8193    1.2667    1.1099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5373    0.8136    0.3551 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1287    1.9932   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843    0.4990    1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9113    0.0694    0.6532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7020   -0.7282   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -1.0153   -1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034   -1.8511   -2.4546 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5600   -3.3587   -2.1157 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6063   -4.2914   -3.3422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7318   -4.3027   -4.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -5.7223   -2.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231   -6.4861   -3.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393   -6.1396   -1.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -3.8516   -4.2609 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6891   -2.3812   -4.6594 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5868   -1.3953   -3.4676 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2007   -0.0214   -4.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -1.2872   -2.7500 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9278   -0.2897   -1.5873 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8099   -0.5380   -0.5283 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3050   -1.7200    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    4.5252    3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2072    4.2579    4.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    4.5737    5.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    3.0247    4.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    1.4035    5.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199    2.8286    6.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275    0.8554    5.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189    2.0794    7.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    1.0630    5.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    2.5972    4.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611   -0.1343    3.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8061    0.8178    3.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    2.7126    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    3.3114    2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    3.6259    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172    0.7659    3.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2954    3.2568    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    2.4648    2.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137    0.4177    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    1.6745    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    1.7622   -1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870    2.9004   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    2.2922   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161   -0.4042    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232   -0.5354    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    0.9317    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181   -1.0850   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -1.6937   -2.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3075   -3.6133   -1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -3.5800   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5537   -4.6218   -3.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980   -3.3201   -4.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -5.0050   -4.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244   -7.0608   -1.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -4.4644   -5.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251   -4.0414   -3.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268   -2.2480   -5.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -2.1370   -5.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0340    0.7469   -3.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -0.0950   -4.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838    0.3418   -4.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763   -2.2664   -2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -0.9674   -3.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102   -0.3101   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    0.7061   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -2.5551   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446   -1.4480    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145   -2.1276    1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 15  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
 18 19  1  0  0  0  0
 32 31  1  0  0  0  0
  4  2  1  0  0  0  0
  2 10  1  0  0  0  0
  8  7  1  0  0  0  0
 31 30  1  0  0  0  0
 21 22  1  1  0  0  0
 30 28  1  0  0  0  0
 28 29  1  1  0  0  0
 15 13  1  0  0  0  0
 19 61  1  1  0  0  0
 27 26  1  0  0  0  0
 13 14  1  1  0  0  0
 26 21  1  0  0  0  0
  8  9  1  1  0  0  0
 21 20  1  0  0  0  0
  4  5  1  1  0  0  0
 18 32  1  0  0  0  0
  2  1  1  1  0  0  0
 15 16  1  0  0  0  0
  2  3  1  6  0  0  0
 13 32  1  0  0  0  0
 10 49  1  6  0  0  0
 18 17  2  0  0  0  0
 21 23  1  6  0  0  0
 17 16  1  0  0  0  0
 32 33  1  6  0  0  0
  8 10  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 28  1  0  0  0  0
  7  6  1  0  0  0  0
 19 20  1  0  0  0  0
  6  4  1  0  0  0  0
 28 27  1  0  0  0  0
 15 57  1  6  0  0  0
 27 70  1  0  0  0  0
 27 71  1  0  0  0  0
 26 68  1  0  0  0  0
 26 69  1  0  0  0  0
 20 62  1  0  0  0  0
 20 63  1  0  0  0  0
 31 77  1  0  0  0  0
 31 78  1  0  0  0  0
 30 75  1  0  0  0  0
 30 76  1  0  0  0  0
 17 60  1  0  0  0  0
 16 58  1  0  0  0  0
 16 59  1  0  0  0  0
 11 50  1  0  0  0  0
 11 51  1  0  0  0  0
 12 52  1  0  0  0  0
 12 53  1  0  0  0  0
  7 44  1  0  0  0  0
  7 45  1  0  0  0  0
 22 64  1  0  0  0  0
 22 65  1  0  0  0  0
 22 66  1  0  0  0  0
 29 72  1  0  0  0  0
 29 73  1  0  0  0  0
 29 74  1  0  0  0  0
 14 54  1  0  0  0  0
 14 55  1  0  0  0  0
 14 56  1  0  0  0  0
  9 46  1  0  0  0  0
  9 47  1  0  0  0  0
  9 48  1  0  0  0  0
  5 41  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
 33 79  1  0  0  0  0
 33 80  1  0  0  0  0
 33 81  1  0  0  0  0
 25 67  1  0  0  0  0
  6 42  1  0  0  0  0
  6 43  1  0  0  0  0
  4 40  1  0  0  0  0
M  END

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
    1.2457    4.0513    4.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442    2.5439    4.6200 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9413    2.4430    5.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    1.8408    5.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3831    2.5784    6.7814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517    1.6372    4.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    0.8936    3.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1615    1.5426    2.5668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5041    2.8580    2.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613    1.7743    3.2479 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5888    2.2941    2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.2667    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373    0.8136    0.3551 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1287    1.9932   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843    0.4990    1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9113    0.0694    0.6532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7020   -0.7282   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -1.0153   -1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034   -1.8511   -2.4546 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5600   -3.3587   -2.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063   -4.2914   -3.3422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7318   -4.3027   -4.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -5.7223   -2.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231   -6.4861   -3.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393   -6.1396   -1.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -3.8516   -4.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6891   -2.3812   -4.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868   -1.3953   -3.4676 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2007   -0.0214   -4.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -1.2872   -2.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278   -0.2897   -1.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8099   -0.5380   -0.5283 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3050   -1.7200    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    4.5252    3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2072    4.2579    4.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    4.5737    5.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    3.0247    4.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    1.4035    5.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199    2.8286    6.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275    0.8554    5.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189    2.0794    7.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    1.0630    5.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    2.5972    4.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611   -0.1343    3.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8061    0.8178    3.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    2.7126    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    3.3114    2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    3.6259    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172    0.7659    3.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2954    3.2568    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    2.4648    2.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137    0.4177    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    1.6745    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    1.7622   -1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870    2.9004   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    2.2922   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161   -0.4042    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232   -0.5354    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    0.9317    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181   -1.0850   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -1.6937   -2.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3075   -3.6133   -1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -3.5800   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5537   -4.6218   -3.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980   -3.3201   -4.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -5.0050   -4.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244   -7.0608   -1.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -4.4644   -5.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251   -4.0414   -3.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268   -2.2480   -5.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -2.1370   -5.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0340    0.7469   -3.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -0.0950   -4.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838    0.3418   -4.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763   -2.2664   -2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -0.9674   -3.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102   -0.3101   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    0.7061   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -2.5551   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446   -1.4480    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145   -2.1276    1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 15  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 18 19  1  0
 32 31  1  0
  4  2  1  0
  2 10  1  0
  8  7  1  0
 31 30  1  0
 21 22  1  1
 30 28  1  0
 28 29  1  1
 15 13  1  0
 19 61  1  1
 27 26  1  0
 13 14  1  1
 26 21  1  0
  8  9  1  1
 21 20  1  0
  4  5  1  1
 18 32  1  0
  2  1  1  1
 15 16  1  0
  2  3  1  6
 13 32  1  0
 10 49  1  6
 18 17  2  0
 21 23  1  6
 17 16  1  0
 32 33  1  6
  8 10  1  0
 23 24  2  0
 23 25  1  0
 19 28  1  0
  7  6  1  0
 19 20  1  0
  6  4  1  0
 28 27  1  0
 15 57  1  6
 27 70  1  0
 27 71  1  0
 26 68  1  0
 26 69  1  0
 20 62  1  0
 20 63  1  0
 31 77  1  0
 31 78  1  0
 30 75  1  0
 30 76  1  0
 17 60  1  0
 16 58  1  0
 16 59  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  0
 12 53  1  0
  7 44  1  0
  7 45  1  0
 22 64  1  0
 22 65  1  0
 22 66  1  0
 29 72  1  0
 29 73  1  0
 29 74  1  0
 14 54  1  0
 14 55  1  0
 14 56  1  0
  9 46  1  0
  9 47  1  0
  9 48  1  0
  5 41  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
 25 67  1  0
  6 42  1  0
  6 43  1  0
  4 40  1  0
M  END

  Mrv1652306102103383D          

 81 85  0  0  0  0            999 V2000
    1.2457    4.0513    4.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442    2.5439    4.6200 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9413    2.4430    5.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    1.8408    5.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3831    2.5784    6.7814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517    1.6372    4.9514 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7883    0.8936    3.6193 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1615    1.5426    2.5668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5041    2.8580    2.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613    1.7743    3.2479 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5888    2.2941    2.2216 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8193    1.2667    1.1099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5373    0.8136    0.3551 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1287    1.9932   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843    0.4990    1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9113    0.0694    0.6532 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7020   -0.7282   -0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -1.0153   -1.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034   -1.8511   -2.4546 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5600   -3.3587   -2.1157 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6063   -4.2914   -3.3422 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7318   -4.3027   -4.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -5.7223   -2.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231   -6.4861   -3.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0393   -6.1396   -1.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624   -3.8516   -4.2609 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6891   -2.3812   -4.6594 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5868   -1.3953   -3.4676 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2007   -0.0214   -4.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511   -1.2872   -2.7500 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9278   -0.2897   -1.5873 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8099   -0.5380   -0.5283 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3050   -1.7200    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850    4.5252    3.7383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2072    4.2579    4.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    4.5737    5.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    3.0247    4.7595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    1.4035    5.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199    2.8286    6.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275    0.8554    5.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189    2.0794    7.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    1.0630    5.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    2.5972    4.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611   -0.1343    3.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8061    0.8178    3.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1677    2.7126    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    3.3114    2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    3.6259    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172    0.7659    3.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2954    3.2568    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    2.4648    2.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137    0.4177    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    1.6745    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    1.7622   -1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870    2.9004   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    2.2922   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161   -0.4042    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232   -0.5354    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    0.9317    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181   -1.0850   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -1.6937   -2.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3075   -3.6133   -1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -3.5800   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5537   -4.6218   -3.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980   -3.3201   -4.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -5.0050   -4.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244   -7.0608   -1.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -4.4644   -5.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251   -4.0414   -3.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268   -2.2480   -5.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -2.1370   -5.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0340    0.7469   -3.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -0.0950   -4.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838    0.3418   -4.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763   -2.2664   -2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -0.9674   -3.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102   -0.3101   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    0.7061   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -2.5551   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446   -1.4480    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145   -2.1276    1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 15  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
 18 19  1  0  0  0  0
 32 31  1  0  0  0  0
  4  2  1  0  0  0  0
  2 10  1  0  0  0  0
  8  7  1  0  0  0  0
 31 30  1  0  0  0  0
 21 22  1  1  0  0  0
 30 28  1  0  0  0  0
 28 29  1  1  0  0  0
 15 13  1  0  0  0  0
 19 61  1  1  0  0  0
 27 26  1  0  0  0  0
 13 14  1  1  0  0  0
 26 21  1  0  0  0  0
  8  9  1  1  0  0  0
 21 20  1  0  0  0  0
  4  5  1  1  0  0  0
 18 32  1  0  0  0  0
  2  1  1  1  0  0  0
 15 16  1  0  0  0  0
  2  3  1  6  0  0  0
 13 32  1  0  0  0  0
 10 49  1  6  0  0  0
 18 17  2  0  0  0  0
 21 23  1  6  0  0  0
 17 16  1  0  0  0  0
 32 33  1  6  0  0  0
  8 10  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 19 28  1  0  0  0  0
  7  6  1  0  0  0  0
 19 20  1  0  0  0  0
  6  4  1  0  0  0  0
 28 27  1  0  0  0  0
 15 57  1  6  0  0  0
 27 70  1  0  0  0  0
 27 71  1  0  0  0  0
 26 68  1  0  0  0  0
 26 69  1  0  0  0  0
 20 62  1  0  0  0  0
 20 63  1  0  0  0  0
 31 77  1  0  0  0  0
 31 78  1  0  0  0  0
 30 75  1  0  0  0  0
 30 76  1  0  0  0  0
 17 60  1  0  0  0  0
 16 58  1  0  0  0  0
 16 59  1  0  0  0  0
 11 50  1  0  0  0  0
 11 51  1  0  0  0  0
 12 52  1  0  0  0  0
 12 53  1  0  0  0  0
  7 44  1  0  0  0  0
  7 45  1  0  0  0  0
 22 64  1  0  0  0  0
 22 65  1  0  0  0  0
 22 66  1  0  0  0  0
 29 72  1  0  0  0  0
 29 73  1  0  0  0  0
 29 74  1  0  0  0  0
 14 54  1  0  0  0  0
 14 55  1  0  0  0  0
 14 56  1  0  0  0  0
  9 46  1  0  0  0  0
  9 47  1  0  0  0  0
  9 48  1  0  0  0  0
  5 41  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
 33 79  1  0  0  0  0
 33 80  1  0  0  0  0
 33 81  1  0  0  0  0
 25 67  1  0  0  0  0
  6 42  1  0  0  0  0
  6 43  1  0  0  0  0
  4 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023969

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]3(C(=C([H])C([H])([H])[C@]4([H])[C@@]5(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]5([H])C([H])([H])C([H])([H])[C@@]34C([H])([H])[H])[C@]2([H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-25(2)21-10-13-30(7)22(28(21,5)12-11-23(25)31)9-8-19-20-18-27(4,24(32)33)15-14-26(20,3)16-17-29(19,30)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,26+,27+,28-,29+,30+/m0/s1

> <INCHI_KEY>
JZFSMVXQUWRSIW-FWXFQHTDSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.7003

> <EXACT_MASS>
456.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.64412076900902

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
7.19

> <JCHEM_LOGP>
6.594833433333333

> <ALOGPS_LOGS>
-5.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433291560097

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.615417665120949

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351234172961267

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
133.62449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-Epikatonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 81 85  0  0  0  0  0  0  0  0999 V2000
    1.2457    4.0513    4.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442    2.5439    4.6200 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9413    2.4430    5.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    1.8408    5.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3831    2.5784    6.7814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517    1.6372    4.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    0.8936    3.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1615    1.5426    2.5668 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5041    2.8580    2.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5613    1.7743    3.2479 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5888    2.2941    2.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.2667    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373    0.8136    0.3551 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1287    1.9932   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843    0.4990    1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.6891   -2.3812   -4.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2846    1.4035    5.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9199    2.8286    6.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275    0.8554    5.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4749    1.0630    5.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693    2.5972    4.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611   -0.1343    3.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1677    2.7126    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1375    3.3114    2.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2176    3.6259    1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9172    0.7659    3.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2954    3.2568    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    2.4648    2.6992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137    0.4177    1.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    1.6745    0.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2639    1.7622   -1.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870    2.9004   -0.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9426    2.2922   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161   -0.4042    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232   -0.5354    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    0.9317    0.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181   -1.0850   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -1.6937   -2.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3075   -3.6133   -1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4337   -3.5800   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5537   -4.6218   -3.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9980   -3.3201   -4.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983   -5.0050   -4.9409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244   -7.0608   -1.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -4.4644   -5.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251   -4.0414   -3.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268   -2.2480   -5.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -2.1370   -5.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0340    0.7469   -3.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2729   -0.0950   -4.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838    0.3418   -4.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763   -2.2664   -2.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -0.9674   -3.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9102   -0.3101   -1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    0.7061   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -2.5551   -0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1446   -1.4480    1.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5145   -2.1276    1.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 15  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 18 19  1  0
 32 31  1  0
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  2 10  1  0
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  2  1  1  1
 15 16  1  0
  2  3  1  6
 13 32  1  0
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 21 23  1  6
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 32 33  1  6
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 23 24  2  0
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  9 47  1  0
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  5 41  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
 25 67  1  0
  6 42  1  0
  6 43  1  0
  4 40  1  0
M  END

HEADER    PROTEIN                                 10-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUN-21         0                                  
HETATM    1  C   UNK     0       1.246   4.051   4.490  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.544   2.544   4.620  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.941   2.443   5.295  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.529   1.841   5.568  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.383   2.578   6.781  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.852   1.637   4.951  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.788   0.894   3.619  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.162   1.543   2.567  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.504   2.858   2.087  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.561   1.774   3.248  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.589   2.294   2.222  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.819   1.267   1.110  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.537   0.814   0.355  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.129   1.993  -0.582  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.384   0.499   1.383  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.911   0.069   0.653  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.702  -0.728  -0.601  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.488  -1.015  -1.168  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.503  -1.851  -2.455  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.560  -3.359  -2.116  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.606  -4.291  -3.342  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.732  -4.303  -4.100  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.876  -5.722  -2.878  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.723  -6.486  -3.312  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.039  -6.140  -1.907  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.762  -3.852  -4.261  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.689  -2.381  -4.659  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.587  -1.395  -3.468  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.201  -0.021  -4.074  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.951  -1.287  -2.750  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.928  -0.290  -1.587  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.810  -0.538  -0.528  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.305  -1.720   0.365  0.00  0.00           C+0
HETATM   34  H   UNK     0       1.885   4.525   3.738  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.207   4.258   4.230  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.433   4.574   5.436  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.698   3.025   4.760  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.285   1.403   5.343  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.920   2.829   6.321  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.928   0.855   5.844  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.219   2.079   7.359  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.475   1.063   5.649  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.369   2.597   4.851  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.461  -0.134   3.825  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.806   0.818   3.217  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.168   2.713   1.234  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.137   3.311   2.853  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.218   3.626   1.805  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.917   0.766   3.520  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.295   3.257   1.796  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.559   2.465   2.699  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.314   0.418   1.587  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.552   1.675   0.402  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.264   1.762  -1.208  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.887   2.900  -0.032  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.943   2.292  -1.248  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.716  -0.404   1.913  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.523  -0.535   1.333  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.521   0.932   0.373  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.618  -1.085  -1.069  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.465  -1.694  -2.953  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.308  -3.613  -1.491  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.434  -3.580  -1.497  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.554  -4.622  -3.448  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.998  -3.320  -4.499  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.698  -5.005  -4.941  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.324  -7.061  -1.732  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.773  -4.464  -5.172  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.725  -4.041  -3.768  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.827  -2.248  -5.325  0.00  0.00           H+0
HETATM   71  H   UNK     0       2.569  -2.137  -5.269  0.00  0.00           H+0
HETATM   72  H   UNK     0       1.034   0.747  -3.315  0.00  0.00           H+0
HETATM   73  H   UNK     0       0.273  -0.095  -4.654  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.984   0.342  -4.749  0.00  0.00           H+0
HETATM   75  H   UNK     0       3.276  -2.266  -2.383  0.00  0.00           H+0
HETATM   76  H   UNK     0       3.722  -0.967  -3.463  0.00  0.00           H+0
HETATM   77  H   UNK     0       3.910  -0.310  -1.097  0.00  0.00           H+0
HETATM   78  H   UNK     0       2.858   0.706  -2.026  0.00  0.00           H+0
HETATM   79  H   UNK     0       2.679  -2.555  -0.232  0.00  0.00           H+0
HETATM   80  H   UNK     0       3.145  -1.448   1.007  0.00  0.00           H+0
HETATM   81  H   UNK     0       1.515  -2.128   1.004  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    4   10    1    3                                             
CONECT    3    2   37   38   39                                             
CONECT    4    2    5    6   40                                             
CONECT    5    4   41                                                       
CONECT    6    7    4   42   43                                             
CONECT    7    8    6   44   45                                             
CONECT    8   15    7    9   10                                             
CONECT    9    8   46   47   48                                             
CONECT   10   11    2   49    8                                             
CONECT   11   10   12   50   51                                             
CONECT   12   11   13   52   53                                             
CONECT   13   12   15   14   32                                             
CONECT   14   13   54   55   56                                             
CONECT   15    8   13   16   57                                             
CONECT   16   15   17   58   59                                             
CONECT   17   18   16   60                                                  
CONECT   18   19   32   17                                                  
CONECT   19   18   61   28   20                                             
CONECT   20   21   19   62   63                                             
CONECT   21   22   26   20   23                                             
CONECT   22   21   64   65   66                                             
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   67                                                       
CONECT   26   27   21   68   69                                             
CONECT   27   26   28   70   71                                             
CONECT   28   30   29   19   27                                             
CONECT   29   28   72   73   74                                             
CONECT   30   31   28   75   76                                             
CONECT   31   32   30   77   78                                             
CONECT   32   31   18   13   33                                             
CONECT   33   32   79   80   81                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    7                                                            
CONECT   46    9                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   11                                                            
CONECT   51   11                                                            
CONECT   52   12                                                            
CONECT   53   12                                                            
CONECT   54   14                                                            
CONECT   55   14                                                            
CONECT   56   14                                                            
CONECT   57   15                                                            
CONECT   58   16                                                            
CONECT   59   16                                                            
CONECT   60   17                                                            
CONECT   61   19                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   22                                                            
CONECT   65   22                                                            
CONECT   66   22                                                            
CONECT   67   25                                                            
CONECT   68   26                                                            
CONECT   69   26                                                            
CONECT   70   27                                                            
CONECT   71   27                                                            
CONECT   72   29                                                            
CONECT   73   29                                                            
CONECT   74   29                                                            
CONECT   75   30                                                            
CONECT   76   30                                                            
CONECT   77   31                                                            
CONECT   78   31                                                            
CONECT   79   33                                                            
CONECT   80   33                                                            
CONECT   81   33                                                            
MASTER        0    0    0    0    0    0    0    0   81    0  170    0
END

RDKit          3D

81 85  0  0  0  0  0  0  0  0999 V2000
    1.2457    4.0513    4.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5286    1.8408    5.5680 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Value	Source
3-Epikatonate	Generator
3-Hydroxy-(3beta,20alpha)-olean-12-en-29-Oic acid	HMDB
Epikatonic acid	HMDB

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7003 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

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

Traditional Name

3-Epikatonic acid

CAS Registry Number

76035-62-6

SMILES

[H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

InChI Identifier

InChI=1S/C30H48O3/c1-25(2)21-10-13-30(7)22(28(21,5)12-11-23(25)31)9-8-19-20-18-27(4,24(32)33)15-14-26(20,3)16-17-29(19,30)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,26+,27+,28-,29+,30+/m0/s1

InChI Key

JZFSMVXQUWRSIW-FWXFQHTDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃ + pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃ + pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃¬†+ pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Austroplenckia populnea	JEOL database	Silva, G. D. F., et al, Magn. Reson. Chem. 40, 366 (2002)
Cornulaca monacantha	LOTUS Database	35616633
Cyamopsis tetragonoloba	JEOL database	Silva, G. D. F., et al, Magn. Reson. Chem. 40, 366 (2002)
Glycyrrhiza glabra	Plant	KNApSAcK
Mukdenia rossii	LOTUS Database	35616633
Plenckia populnea	LOTUS Database	35616633
Sandoricum indicum	KNApSAcK Database	22123792
Sandoricum koetjape	Plant	KNApSAcK
Spermacoce articularis	LOTUS Database	35616633
Tripterygium doianum	KNApSAcK Database	22123792
Tripterygium hypoglaucum	KNApSAcK Database	22123792
Tripterygium wilfordii	JEOL database	Silva, G. D. F., et al, Magn. Reson. Chem. 40, 366 (2002)
Tripterygium wilfordii Hook f.	KNApSAcK Database	22123792

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

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	7.19	ALOGPS
logP	6.59	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	54.64 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

HMDB0034655

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013179

KNApSAcK ID

C00036544

Chemspider ID

8609651

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10434225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1844901

References

General References

Duarte LP, Vieira Filho SA, Silva GD, de Sousa JR, Pinto Ada S: Anti-trypanosomal activity of pentacyclic triterpenes isolated from Austroplenckia populnea (Celastraceae). Rev Inst Med Trop Sao Paulo. 2002 Mar-Apr;44(2):109-12. doi: 10.1590/s0036-46652002000200010. [PubMed:12048549 ]
G. D. F. Silva, L. P. Duarte, S. A. Vieira Filho, A. C. Doriguetto, Y. P. Mascarenhas, J. Ellena, E. E. Castellano, A. B. Cota (2002). G. D. F. Silva, L. P. Duarte, S. A. Vieira Filho, A. C. Doriguetto, Y. P. Mascarenhas, J. Ellena, E. E. Castellano, A. B. Cota. Epikatonic acid from Austroplenckia populnea: structure elucidation by 2D NMR spectroscopy and X‐ray crystallography. Magn. Reson. Chem. 40(5), 366-370. Magnetic Resonance in Chemistry.
JEOL [Link]

Showing NP-Card for 3-Epikatonic acid (NP0023969)

MOL for NP0023969 (3-Epikatonic acid)

3D MOL for NP0023969 (3-Epikatonic acid)

3D SDF for NP0023969 (3-Epikatonic acid)

3D-SDF for NP0023969 (3-Epikatonic acid)

PDB for NP0023969 (3-Epikatonic acid)

3D PDB for NP0023969 (3-Epikatonic acid)

SMILES for NP0023969 (3-Epikatonic acid)

INCHI for NP0023969 (3-Epikatonic acid)

Structure for NP0023969 (3-Epikatonic acid)

3D Structure for NP0023969 (3-Epikatonic acid)