NP-MRD: Showing NP-Card for (1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate (NP0227546)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 06:53:36 UTC

Updated at

2022-09-06 06:53:36 UTC

NP-MRD ID

NP0227546

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate

Description

16Beta-Hydroxyalisol B 23-acetate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate is found in Alisma plantago-aquatica. (1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate was first documented in 2012 (PMID: 23212633). Based on a literature review very few articles have been published on 16beta-Hydroxyalisol B 23-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062208532D          

 38 42  0  0  1  0            999 V2000
   -3.0459   -1.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9178   -0.1264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7223   -1.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051   -1.4291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3987   -2.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7294   -1.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6252   -1.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9702   -4.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0804   -3.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942   -0.6649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7071    0.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -0.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6618    0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7913   -0.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  6  0  0  0
 34  5  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END

     RDKit          3D

 88 92  0  0  0  0  0  0  0  0999 V2000
    3.5972    0.0177    3.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5957   -0.3907    2.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8142   -1.2681    2.0164 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4564    0.1973    1.5101 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   -0.1795    0.1495 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1407    0.9344   -0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090    1.5859   -0.6210 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7418    2.6878   -1.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582    0.6525   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695    0.2854   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3177    0.6123    1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1337    1.1282    1.2077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3951    1.2872    2.5830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0154    0.0470    0.6050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4554    0.1860    0.9564 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6834   -0.5100    2.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9498    1.6057    1.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3001    1.4792    1.8481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2003    0.5501    1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4036    0.6600    1.3514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7642   -0.5316    0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1267   -1.9037    0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6021   -0.3076   -1.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3430   -0.3769   -0.1558 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6736   -1.6128   -0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5339   -1.1107   -1.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7048   -0.0919   -0.8409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7029    1.2138   -1.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -0.6102   -0.9357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1171   -1.9819   -0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1695   -0.6424   -2.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5067    0.0057   -2.3152 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5151   -0.9388   -2.5454 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7286   -0.9336   -0.1845 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8079   -1.3321   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8648   -0.5345   -0.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1251    0.7091   -1.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1407   -1.3808   -0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7712   -0.4991    4.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5494   -0.2866    4.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4485    1.1265    3.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198   -0.9431    0.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643    0.5892   -1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815    1.6718   -0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332    2.0188    0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754    2.9773   -1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1256    2.2396   -2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340    3.5591   -1.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9361    1.3943    1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904   -0.2762    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385    2.0698    0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6846    1.9184    2.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6314   -0.9069    1.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6785   -0.8884    2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4548    0.2326    3.0797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9204   -1.3283    2.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2316    2.0699    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302    2.2551    1.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7572    2.5076    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1778    1.3106    2.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2184   -2.5667    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7176   -1.8826    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7848   -2.4718    0.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3247    0.6816   -1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3849   -1.0779   -1.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6843   -0.3465   -0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3006    0.4200   -0.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2910   -2.1717    0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3631   -2.2331   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -1.9251   -2.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753   -0.6006   -2.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    1.0713   -2.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1741    2.0436   -1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6933    1.5480   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3048   -1.9593    0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073   -2.6033   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6694   -2.5213   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2786   -1.7007   -2.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396   -0.1372   -3.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6029    0.8452   -3.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767   -0.9068   -3.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7823   -1.9234    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1104    0.5826   -2.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3353    1.5579   -0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4110    0.9321   -2.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9961   -2.0933    0.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4104   -1.9250   -1.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9406   -0.6555   -0.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 36 34  1  0
 32  9  1  0
 29 10  1  0
 27 14  1  0
 24 15  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  7 45  1  1
  6 43  1  0
  6 44  1  0
  5 42  1  1
  1 39  1  0
  1 40  1  0
  1 41  1  0
 34 82  1  1
 37 83  1  0
 37 84  1  0
 37 85  1  0
 38 86  1  0
 38 87  1  0
 38 88  1  0
 11 49  1  0
 11 50  1  0
 12 51  1  6
 13 52  1  0
 14 53  1  1
 16 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  6
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 28 72  1  0
 28 73  1  0
 28 74  1  0
 30 75  1  0
 30 76  1  0
 30 77  1  0
 31 78  1  0
 31 79  1  0
 32 80  1  6
 33 81  1  0
M  END


  Mrv1652309062208532D          

 38 42  0  0  1  0            999 V2000
   -3.0459   -1.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287   -0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9178   -0.1264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7223   -1.5419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051   -1.4291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3987   -2.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4185   -1.9676    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7294   -1.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6252   -1.4759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9702   -4.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0804   -3.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5942   -0.6649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7071    0.1523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -0.1585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6618    0.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7913   -0.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  6  0  0  0
 34  5  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227546

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](C[C@H](OC(C)=O)[C@H]1OC1(C)C)C1=C2C[C@H](O)[C@H]3[C@@]4(C)CCC(=O)C(C)(C)[C@@H]4CC[C@]3(C)[C@@]2(C)C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O6/c1-17(14-22(37-18(2)33)27-29(5,6)38-27)25-19-15-20(34)26-30(7)12-11-24(36)28(3,4)23(30)10-13-31(26,8)32(19,9)16-21(25)35/h17,20-23,26-27,34-35H,10-16H2,1-9H3/t17-,20+,21+,22+,23+,26+,27-,30+,31+,32+/m1/s1

> <INCHI_KEY>
QXTFJHAHEZDLDP-XKFNBYHKSA-N

> <FORMULA>
C32H50O6

> <MOLECULAR_WEIGHT>
530.746

> <EXACT_MASS>
530.36073933

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
60.16423340111737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R)-3-[(1S,2S,7R,10S,11R,13S,17S)-13,17-dihydroxy-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-en-14-yl]-1-[(2R)-3,3-dimethyloxiran-2-yl]butyl acetate

> <JCHEM_LOGP>
4.118110927666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.93744378501136

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.09278921567746

> <JCHEM_PKA_STRONGEST_BASIC>
-0.25505614219177886

> <JCHEM_POLAR_SURFACE_AREA>
96.36

> <JCHEM_REFRACTIVITY>
146.1809

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R)-3-[(1S,2S,7R,10S,11R,13S,17S)-13,17-dihydroxy-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-en-14-yl]-1-[(2R)-3,3-dimethyloxiran-2-yl]butyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.686  -1.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.160  -1.662   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.580  -0.236   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.215  -2.878   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.690  -2.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.744  -3.883   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.362  -2.246   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.767  -2.755   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.312  -7.735   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.678  -7.823   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.150  -6.891   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.109  -1.241   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.320   0.284   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.107  -0.296   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.235   0.752   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.477  -0.998   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   27                                                  
CONECT   15   14   16   17   24                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   15   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   14   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   10   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    9   33                                                  
CONECT   33   32                                                            
CONECT   34    5   35   36                                                  
CONECT   35   34   36                                                       
CONECT   36   35   34   37   38                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
16b-Hydroxyalisol b 23-acetate	Generator
16b-Hydroxyalisol b 23-acetic acid	Generator
16beta-Hydroxyalisol b 23-acetic acid	Generator
16Β-hydroxyalisol b 23-acetate	Generator
16Β-hydroxyalisol b 23-acetic acid	Generator

Chemical Formula

C₃₂H₅₀O₆

Average Mass

530.7460 Da

Monoisotopic Mass

530.36074 Da

IUPAC Name

(1S,3R)-3-[(1S,2S,7R,10S,11R,13S,17S)-13,17-dihydroxy-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-en-14-yl]-1-[(2R)-3,3-dimethyloxiran-2-yl]butyl acetate

Traditional Name

(1S,3R)-3-[(1S,2S,7R,10S,11R,13S,17S)-13,17-dihydroxy-2,6,6,10,11-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-14-en-14-yl]-1-[(2R)-3,3-dimethyloxiran-2-yl]butyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](C[C@H](OC(C)=O)[C@H]1OC1(C)C)C1=C2C[C@H](O)[C@H]3[C@@]4(C)CCC(=O)C(C)(C)[C@@H]4CC[C@]3(C)[C@@]2(C)C[C@@H]1O

InChI Identifier

InChI=1S/C32H50O6/c1-17(14-22(37-18(2)33)27-29(5,6)38-27)25-19-15-20(34)26-30(7)12-11-24(36)28(3,4)23(30)10-13-31(26,8)32(19,9)16-21(25)35/h17,20-23,26-27,34-35H,10-16H2,1-9H3/t17-,20+,21+,22+,23+,26+,27-,30+,31+,32+/m1/s1

InChI Key

QXTFJHAHEZDLDP-XKFNBYHKSA-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
Alisma plantago-aquatica	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
Steroid ester
3-oxosteroid
Hydroxysteroid
Oxosteroid
3-oxo-5-alpha-steroid
16-hydroxysteroid
11-hydroxysteroid
16-beta-hydroxysteroid
11-beta-hydroxysteroid
Steroid
Cyclic alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	4.12	ChemAxon
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	146.18 m³·mol⁻¹	ChemAxon
Polarizability	60.16 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101664416

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jin HG, Jin Q, Ryun Kim A, Choi H, Lee JH, Kim YS, Lee DG, Woo ER: A new triterpenoid from Alisma orientale and their antibacterial effect. Arch Pharm Res. 2012 Nov;35(11):1919-26. doi: 10.1007/s12272-012-1108-5. Epub 2012 Dec 4. [PubMed:23212633 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate (NP0227546)

MOL for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

3D MOL for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

3D SDF for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

3D-SDF for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

PDB for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

3D PDB for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

SMILES for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

INCHI for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

Structure for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)

3D Structure for NP0227546 ((1s,3r)-3-[(2s,3ar,3bs,5ar,9as,9bs,10s)-2,10-dihydroxy-3a,3b,6,6,9a-pentamethyl-7-oxo-2h,3h,4h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-[(2r)-3,3-dimethyloxiran-2-yl]butyl acetate)