NP-MRD: Showing NP-Card for Eichlerianic acid (NP0075313)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 20:36:22 UTC

Updated at

2022-04-28 20:36:22 UTC

NP-MRD ID

NP0075313

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eichlerianic acid

Description

Eichlerianic acid, also known as eichlerianate, belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Eichlerianic acid is found in Aglaia elaeagnoidea, Aglaia elliptica, Aglaia foveolata, Aglaia lawii, Aglaia leucophylla, Aglaia perviridis, Aglaia rubiginosa, Cabralea canjerana, Cabralea eichleriana and Dysoxylum hainanense. Eichlerianic acid was first documented in 2016 (PMID: 25742723). Based on a literature review very few articles have been published on eichlerianic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222362D          

 34 37  0  0  1  0            999 V2000
    2.3637    0.3610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3612    1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3066    2.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4335    2.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4881    3.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1192    2.3271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3215    1.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    1.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -0.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    1.3982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7351    2.0502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5113    1.7708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4856    0.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6934    0.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1936    2.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8759    2.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6574    1.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7298    2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340    1.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519   -0.4564    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  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 16  1  1  0  0  0
  9 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  6 20  1  1  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  1 23  1  0  0  0  0
 21 24  1  1  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 26 29  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 24 33  1  6  0  0  0
  1 34  1  6  0  0  0
M  END

     RDKit          3D

 84 87  0  0  0  0  0  0  0  0999 V2000
   -5.8794    2.1951   -1.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0930    1.8907   -0.2256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6589    2.2797    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781    1.3196   -0.4336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3390    1.4342   -1.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0203    0.9006   -2.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702   -0.0607   -1.2977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2311   -1.4100   -1.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9906   -0.1018    0.0798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3015   -0.9607    1.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1858   -0.5701    1.1768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8005   -0.4839   -0.1607 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1558    0.1123   -0.2688 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3058   -0.5744    0.3236 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5516   -1.9741   -0.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380   -0.5803    1.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889   -0.2653    2.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1281    0.5497    1.0500 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6194    0.3934    0.7349 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8972   -1.0025    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8632    1.3273   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4235    0.7691    1.7837 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461    0.1478   -0.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2734    0.2463   -1.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8734    0.5668   -2.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0353    0.4678   -1.0591 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0126    1.8709   -0.4396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5153   -0.1162    0.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0950   -1.0409   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0394   -0.2946    1.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0548   -1.5786    2.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9708   -2.6354    1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9323   -2.3928    0.9012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7549   -3.9859    1.9701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6840    2.0142   -2.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8584    2.6968   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669    2.3249    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6072    1.7715    1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9659    3.3830    0.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    1.9459    0.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1443    0.9985   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935    2.5431   -2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1296    0.3650   -3.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410    1.7376   -2.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532   -2.2456   -1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1794   -1.6486   -2.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672   -1.4524   -2.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527    0.9585    0.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4183   -2.0306    0.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738   -0.6345    2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6222   -1.4490    1.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3238    0.2938    1.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469   -1.4908   -0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1257    1.1530    0.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047   -2.4800    0.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.9265   -1.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621   -2.5907   -0.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6594    0.2782    2.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9353   -1.5565    2.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2134   -1.2151    2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    0.3389    3.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9855    1.6395    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2916   -1.1088   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6144   -1.7659    0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9501   -1.0641   -0.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1616    2.1919   -0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6055    0.7949   -1.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8956    1.6907   -0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4956    1.7521    1.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -0.7588   -2.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0235    0.9866   -2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    0.0062   -3.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9394    1.6375   -2.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654    2.4586   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1415    1.8752    0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877    2.4811   -0.8250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1802   -0.8331   -1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7330   -0.8221   -1.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9490   -2.1063   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6302    0.5250    2.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1459    0.0040    1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4660   -1.3143    3.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1436   -2.0959    2.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3794   -4.6996    1.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 23  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  1
  9 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 34  1  0
 32 33  2  0
 28  4  1  0
 26  7  1  0
 23 14  1  0
 26 12  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  1 35  1  0
  1 36  1  0
  4 40  1  1
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  1
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  6
 13 54  1  1
 24 70  1  0
 24 71  1  0
 25 72  1  0
 25 73  1  0
 27 74  1  0
 27 75  1  0
 27 76  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 16 59  1  0
 17 60  1  0
 17 61  1  0
 18 62  1  1
 20 63  1  0
 20 64  1  0
 20 65  1  0
 21 66  1  0
 21 67  1  0
 21 68  1  0
 22 69  1  0
 29 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 31 82  1  0
 31 83  1  0
 34 84  1  0
M  END


  Mrv1652304282222362D          

 34 37  0  0  1  0            999 V2000
    2.3637    0.3610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3612    1.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3066    2.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4335    2.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4881    3.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1192    2.3271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3215    1.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    1.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -0.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    1.3982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7351    2.0502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5113    1.7708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4856    0.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6934    0.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1936    2.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8759    2.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6574    1.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7298    2.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340    1.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519   -0.4564    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  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 16  1  1  0  0  0
  9 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  6 20  1  1  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  1 23  1  0  0  0  0
 21 24  1  1  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 26 29  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 24 33  1  6  0  0  0
  1 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075313

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H](CC[C@@]23C)[C@]2(C)CC[C@H](O2)C(C)(C)O)[C@@]1(C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O4/c1-19(2)20-11-17-29(7)23(27(20,5)15-14-25(31)32)10-9-21-22(12-16-28(21,29)6)30(8)18-13-24(34-30)26(3,4)33/h20-24,33H,1,9-18H2,2-8H3,(H,31,32)/t20-,21+,22-,23+,24-,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
ZKBGKWZSOPPDSD-ZFQFSHTNSA-N

> <FORMULA>
C30H50O4

> <MOLECULAR_WEIGHT>
474.726

> <EXACT_MASS>
474.37091009

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
56.70732993631717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
6.033138302333333

> <ALOGPS_LOGS>
-6.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.32532879455551

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.966703743683387

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0939011853446026

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
136.3364

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.674   2.984   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.572   4.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.809   5.200   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.911   6.737   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.089   4.344   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.600   3.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.745   0.866   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.473   2.223   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.556  -0.443   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.601  -0.635   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.895   2.610   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.839   3.827   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.288   3.306   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.240   1.766   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.761   1.336   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.561   4.171   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.835   5.037   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.427   2.898   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.696   5.445   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.783   3.676   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.203  -0.852   0.000  0.00  0.00           C+0
CONECT    1    2    6   23   34                                             
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9    5   11   16                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10                                                            
CONECT   17    9   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    6                                                            
CONECT   21    2   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22    1                                                       
CONECT   24   21   25   28   33                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   26   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33   24                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Eichlerianate	Generator

Chemical Formula

C₃₀H₅₀O₄

Average Mass

474.7260 Da

Monoisotopic Mass

474.37091 Da

IUPAC Name

3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid

Traditional Name

3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H](CC[C@@]23C)[C@]2(C)CC[C@H](O2)C(C)(C)O)[C@@]1(C)CCC(O)=O

InChI Identifier

InChI=1S/C30H50O4/c1-19(2)20-11-17-29(7)23(27(20,5)15-14-25(31)32)10-9-21-22(12-16-28(21,29)6)30(8)18-13-24(34-30)26(3,4)33/h20-24,33H,1,9-18H2,2-8H3,(H,31,32)/t20-,21+,22-,23+,24-,27-,28+,29+,30-/m0/s1

InChI Key

ZKBGKWZSOPPDSD-ZFQFSHTNSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aglaia elaeagnoidea	LOTUS Database	35616633
Aglaia elliptica	LOTUS Database	35616633
Aglaia foveolata	Plant	KNApSAcK
Aglaia lawii	Plant	KNApSAcK
Aglaia leucophylla	LOTUS Database	35616633
Aglaia perviridis	LOTUS Database	35616633
Aglaia rubiginosa	LOTUS Database	35616633
Cabralea canjerana	LOTUS Database	35616633
Cabralea eichleriana	-	KNApSAcK
Dysoxylum hainanense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Seco-podocarpan diterpenoid
Carbocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

diterpene glycoside (CHEBI:70463 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.86	ALOGPS
logP	6.03	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.97	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.34 m³·mol⁻¹	ChemAxon
Polarizability	56.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033955

Chemspider ID

10250722

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12315516

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu B, Xu YK: Cytotoxicity and Synergistic Effect of the Constituents from Roots of Aglaia odorata (Meliaceae). Nat Prod Res. 2016;30(4):433-7. doi: 10.1080/14786419.2015.1016940. Epub 2015 Mar 6. [PubMed:25742723 ]

Showing NP-Card for Eichlerianic acid (NP0075313)

MOL for NP0075313 (Eichlerianic acid)

3D MOL for NP0075313 (Eichlerianic acid)

3D SDF for NP0075313 (Eichlerianic acid)

3D-SDF for NP0075313 (Eichlerianic acid)

PDB for NP0075313 (Eichlerianic acid)

3D PDB for NP0075313 (Eichlerianic acid)

SMILES for NP0075313 (Eichlerianic acid)

INCHI for NP0075313 (Eichlerianic acid)

Structure for NP0075313 (Eichlerianic acid)

3D Structure for NP0075313 (Eichlerianic acid)