NP-MRD: Showing NP-Card for (3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one (NP0168763)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 04:37:18 UTC

Updated at

2022-09-03 04:37:18 UTC

NP-MRD ID

NP0168763

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one

Description

CHEMBL494049 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one is found in Ajuga decumbens and Ajuga reptans. Based on a literature review very few articles have been published on CHEMBL494049.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032206372D          

 38 42  0  0  1  0            999 V2000
    1.7372   -5.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613   -5.1231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2784   -5.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2516   -6.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3729   -5.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -4.3038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5556   -3.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.3306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556   -3.7922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2132   -3.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8898   -0.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  1  0  0  0
 15 12  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 20  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 15 37  1  0  0  0  0
 18 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END

     RDKit          3D

 82 86  0  0  0  0  0  0  0  0999 V2000
    6.5867    1.6548    1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137    0.6797    0.7031 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3087    0.8299   -0.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5010    0.6377   -1.1155 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2182    1.2139   -1.4779 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3339    1.9091   -0.6193 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9155    3.2871   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3958    1.0520    0.6172 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3627    0.0011    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3944   -0.9883   -0.4636 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7126   -1.5477   -0.3260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -2.1800   -0.2645 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8550   -2.8700    1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9877   -3.1013   -1.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938   -2.0716   -0.6433 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4434   -3.4402   -0.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251   -3.1532   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709   -1.8140   -0.7229 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1390   -1.8916   -2.0961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460   -1.0536   -0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744   -1.6914    0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4487   -0.9715    0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5507   -1.5682    0.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2417    0.4622    1.1716 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6274    0.4896    2.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6061    1.0924    1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4638    0.8972    0.1182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3878    1.9690    0.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5727    0.9764   -1.1062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3070    1.6065   -2.1097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4025    1.8974   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4221    1.1790    0.1612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7306    2.3310    0.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173    0.3856   -0.5846 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0604    1.0515   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0526    0.1876   -0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1183   -1.1066   -0.1952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1320   -0.8609    1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201    2.5150    1.8889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8085    1.1408    2.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5270    1.9669    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0820   -0.3124    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3117    1.9813   -1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0360    3.2554   -0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878    3.8097    0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6699    3.8765   -1.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1800    1.7630    1.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5069   -0.5847    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903    0.4948    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560   -0.5592   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592   -2.3670   -0.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9459   -2.6188    1.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8960   -3.9823    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3439   -2.5504    1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -2.6978   -2.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449   -2.0514   -1.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5544   -4.1498   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -3.9055    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2337   -3.1049    1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6602   -3.9384   -0.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884   -1.8580   -2.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987   -2.7674    0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1989   -0.0946    3.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1034    0.5566    2.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5466    2.1611    1.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0872   -0.0123    0.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1684    2.6365   -0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2522    0.0043   -1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8696    0.9039   -2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8716    2.1991   -1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8407    2.7632   -0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1342    2.9592    0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5914    2.9848    1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2477    1.9981    1.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7116    0.4324   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068    1.9398   -1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    1.4319    0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632    0.7701   -1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763   -0.1230   -2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2520    0.1101    1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202   -1.7032    1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2497   -0.7535    1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  6
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  1
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  1
  8  6  1  0
 37 15  1  0
 37 18  1  0
 34 20  1  0
 32 24  1  0
  7 44  1  0
  7 45  1  0
  7 46  1  0
  6 43  1  6
  2 42  1  1
  1 39  1  0
  1 40  1  0
  1 41  1  0
  8 47  1  1
  9 48  1  0
  9 49  1  0
 10 50  1  6
 11 51  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 15 56  1  6
 16 57  1  0
 16 58  1  0
 17 59  1  0
 17 60  1  0
 19 61  1  0
 21 62  1  0
 25 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  1
 28 67  1  0
 29 68  1  6
 30 69  1  0
 31 70  1  0
 31 71  1  0
 33 72  1  0
 33 73  1  0
 33 74  1  0
 34 75  1  6
 35 76  1  0
 35 77  1  0
 36 78  1  0
 36 79  1  0
 38 80  1  0
 38 81  1  0
 38 82  1  0
M  END


  Mrv1652309032206372D          

 38 42  0  0  1  0            999 V2000
    1.7372   -5.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613   -5.1231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2784   -5.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2516   -6.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3729   -5.0798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0926   -4.3038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5556   -3.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.3306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556   -3.7922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2132   -3.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8898   -0.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  1  0  0  0
 15 12  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 20  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 15 37  1  0  0  0  0
 18 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0168763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(=O)[C@@H](C)[C@@H]1C[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@]4(O)C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O9/c1-14-16(15(2)38-24(14)34)10-22(32)27(5,35)21-7-9-28(36)18-11-23(33)29(37)13-20(31)19(30)12-26(29,4)17(18)6-8-25(21,28)3/h11,14-17,19-22,30-32,35-37H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,20+,21-,22+,25+,26+,27+,28+,29+/m0/s1

> <INCHI_KEY>
YQCOGGGDJXBMBU-JIVHLSMOSA-N

> <FORMULA>
C29H44O9

> <MOLECULAR_WEIGHT>
536.662

> <EXACT_MASS>
536.298532997

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.58841580298886

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(1R,2R,4S,5R,7S,11S,14S,15R)-4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]butyl]-3,5-dimethyloxolan-2-one

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
0.2058235366666677

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.314575247729373

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.492374285440814

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1574315713505037

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
137.41429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(1R,2R,4S,5R,7S,11S,14S,15R)-4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]butyl]-3,5-dimethyloxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.243 -10.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.794  -9.563   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.520 -10.427   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.470 -11.967   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.696  -9.482   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.173  -8.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.037  -6.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.366  -8.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.998  -6.808   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.566  -4.918   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   37                                             
CONECT   19   18                                                            
CONECT   20   18   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   32                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   24   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   20   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   15   18   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₄O₉

Average Mass

536.6620 Da

Monoisotopic Mass

536.29853 Da

IUPAC Name

(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(1R,2R,4S,5R,7S,11S,14S,15R)-4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]butyl]-3,5-dimethyloxolan-2-one

Traditional Name

(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(1R,2R,4S,5R,7S,11S,14S,15R)-4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]butyl]-3,5-dimethyloxolan-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(=O)[C@@H](C)[C@@H]1C[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@]4(O)C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C29H44O9/c1-14-16(15(2)38-24(14)34)10-22(32)27(5,35)21-7-9-28(36)18-11-23(33)29(37)13-20(31)19(30)12-26(29,4)17(18)6-8-25(21,28)3/h11,14-17,19-22,30-32,35-37H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,20+,21-,22+,25+,26+,27+,28+,29+/m0/s1

InChI Key

YQCOGGGDJXBMBU-JIVHLSMOSA-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
Ajuga decumbens	LOTUS Database	35616633
Ajuga reptans	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
Hexahydroxy bile acid, alcohol, or derivatives
Cholesterol-skeleton
Cholestane-skeleton
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
Steroid lactone
Bile acid, alcohol, or derivatives
20-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
14-hydroxysteroid
3-hydroxysteroid
2-hydroxysteroid
Oxosteroid
3-hydroxy-delta-7-steroid
6-oxosteroid
5-hydroxysteroid
Delta-7-steroid
Steroid
Cyclohexenone
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.95	ALOGPS
logP	0.21	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	12.49	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	137.41 m³·mol⁻¹	ChemAxon
Polarizability	57.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23339056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12442769

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one (NP0168763)

MOL for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

3D MOL for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

3D SDF for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

3D-SDF for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

PDB for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

3D PDB for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

SMILES for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

INCHI for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

Structure for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)

3D Structure for NP0168763 ((3s,4s,5r)-4-[(2r,3r)-3-[(1s,3as,5as,7r,8s,9ar,9br,11ar)-3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2,3-dihydroxybutyl]-3,5-dimethyloxolan-2-one)