NP-MRD: Showing NP-Card for (1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione (NP0226868)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 06:02:16 UTC

Updated at

2022-09-06 06:02:16 UTC

NP-MRD ID

NP0226868

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione

Description

(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-14-[(2S,4R,5E)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,17-dione belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. (1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione is found in Cucumis melo. Based on a literature review very few articles have been published on (1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-14-[(2S,4R,5E)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062208022D          

 37 40  0  0  1  0            999 V2000
   -2.5808    2.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    1.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3854    0.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5135   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585   -1.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5060   -2.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1983   -2.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6359   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643   -3.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -3.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995   -0.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044    2.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7217    2.6394    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  6  0  0  0
 10  7  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 20 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 10 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  6  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

 83 86  0  0  0  0  0  0  0  0999 V2000
    7.8657    0.5839    0.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8607    0.9332   -0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5387    1.0144   -0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1066    0.7380    0.9835 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8944   -0.2373    1.6161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6478    0.5115    1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044   -0.6330    0.5241 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7507   -1.9537    0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2003   -0.5320   -0.8306 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5991   -0.9087    0.8113 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2478   -1.2211    2.2369 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7199   -2.4362    2.6966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.2383    2.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6979   -0.8987    0.8517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6821   -2.1830    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087   -0.1918    0.8056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1422   -1.0276    1.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4144   -0.2313    1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6279    0.1947   -0.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5733   -0.1897   -1.0912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8589    0.1830   -2.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3511    0.0966   -2.7374 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6200    0.3100   -4.0929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9921    1.1487   -1.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5887    2.0576   -2.4006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8350    0.9814   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0731    0.2012    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8933    2.3303    0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2828    0.4121   -0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6176    1.9017   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1518    0.3277   -1.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672    0.3682   -2.6571 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    0.1922   -1.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4851   -0.0275    0.4051 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5586    1.2885    1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3446    1.2076   -2.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2290    2.2830   -2.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7175    1.1487    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8705    0.8902   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9431   -0.5019    0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9430    1.2899   -1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3463    1.6783    1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6450   -0.1994    2.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4922    0.5423    2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1880    1.4775    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0839   -2.7725    0.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670   -2.0424    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897   -2.0386    1.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9019    0.2700   -1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836   -1.8944    0.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5665   -0.4642    2.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219   -3.2295    2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6654   -2.2251    2.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -0.4516    2.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7213   -2.5557   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187   -2.0870   -0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -3.0457    0.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642    0.6299    1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0184   -1.1788    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3185   -1.9801    0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0812   -0.0338    1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5625   -1.3135   -1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5501    1.1988   -2.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198   -0.6006   -3.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6947   -0.9196   -2.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3323   -0.5060   -4.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1674   -0.7477   -0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9757    0.8369   -0.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9336   -0.0444    1.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9296    2.5509    0.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6227    3.0988   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2322    2.3705    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3191    2.2812   -1.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957    2.0533    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591    2.4668   -0.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7437    1.1989   -1.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7779   -0.5430   -1.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1833    1.2617    2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3761    1.7513    1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594    2.0278    0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9694    0.3014   -2.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5247    1.3014   -2.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1033    2.0393   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 36  1  0
 36 37  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 20 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  1
 34 10  1  0
 34 14  1  0
 29 16  1  0
 26 19  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 36 81  1  0
 36 82  1  0
 37 83  1  0
  3 41  1  0
  4 42  1  1
  5 43  1  0
  6 44  1  0
  6 45  1  0
  8 46  1  0
  8 47  1  0
  8 48  1  0
  9 49  1  0
 10 50  1  6
 11 51  1  1
 12 52  1  0
 13 53  1  0
 13 54  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  1
 17 59  1  0
 17 60  1  0
 18 61  1  0
 20 62  1  6
 21 63  1  0
 21 64  1  0
 22 65  1  1
 23 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 28 72  1  0
 30 73  1  0
 30 74  1  0
 30 75  1  0
 33 76  1  0
 33 77  1  0
 35 78  1  0
 35 79  1  0
 35 80  1  0
M  END


  Mrv1652309062208022D          

 37 40  0  0  1  0            999 V2000
   -2.5808    2.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    1.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3854    0.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5135   -0.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585   -1.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5060   -2.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1983   -2.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6359   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643   -3.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -3.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995   -0.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9044    2.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7217    2.6394    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  6  0  0  0
 10  7  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 20 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 10 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  6  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226868

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CO)=C/[C@H](O)C[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@H](O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O7/c1-16(15-31)10-17(32)12-29(6,37)24-21(34)13-27(4)22-9-8-18-19(11-20(33)25(36)26(18,2)3)30(22,7)23(35)14-28(24,27)5/h8,10,17,19-22,24,31-34,37H,9,11-15H2,1-7H3/b16-10+/t17-,19+,20-,21+,22-,24-,27-,28+,29-,30-/m0/s1

> <INCHI_KEY>
OTNVTCVBBIOOBO-OGRZDRPTSA-N

> <FORMULA>
C30H46O7

> <MOLECULAR_WEIGHT>
518.691

> <EXACT_MASS>
518.324353821

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.575929000530664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-14-[(2S,4R,5E)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione

> <JCHEM_LOGP>
1.530763514666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.235686973422368

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.302894278163347

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7309129905613556

> <JCHEM_POLAR_SURFACE_AREA>
135.29

> <JCHEM_REFRACTIVITY>
142.6738

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-14-[(2S,4R,5E)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione

> <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      -4.818   4.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.343   3.922   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.923   2.495   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.978   1.280   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.453   1.490   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -6.559  -0.147   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.398  -0.418   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.829  -2.308   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.545  -4.581   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.237  -5.472   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.920  -1.258   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.600  -6.094   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.240  -6.586   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.372  -0.445   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.288   5.138   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -8.814   4.927   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   34                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   34                                             
CONECT   15   14                                                            
CONECT   16   14   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   20   16   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   10   14   35                                             
CONECT   35   34                                                            
CONECT   36    2   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₇

Average Mass

518.6910 Da

Monoisotopic Mass

518.32435 Da

IUPAC Name

(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-14-[(2S,4R,5E)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione

Traditional Name

(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-14-[(2S,4R,5E)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione

CAS Registry Number

Not Available

SMILES

C\C(CO)=C/[C@H](O)C[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@H](O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

InChI Identifier

InChI=1S/C30H46O7/c1-16(15-31)10-17(32)12-29(6,37)24-21(34)13-27(4)22-9-8-18-19(11-20(33)25(36)26(18,2)3)30(22,7)23(35)14-28(24,27)5/h8,10,17,19-22,24,31-34,37H,9,11-15H2,1-7H3/b16-10+/t17-,19+,20-,21+,22-,24-,27-,28+,29-,30-/m0/s1

InChI Key

OTNVTCVBBIOOBO-OGRZDRPTSA-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
Cucumis melo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Cucurbitacin skeleton
Triterpenoid
26-hydroxysteroid
23-hydroxysteroid
20-hydroxysteroid
3-oxo-delta-5-steroid
3-oxosteroid
14-alpha-methylsteroid
2-hydroxysteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Hydroxysteroid
11-oxosteroid
Oxosteroid
Delta-5-steroid
Fatty alcohol
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Polyol
Organooxygen compound
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.53	ChemAxon
pKa (Strongest Acidic)	13.3	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.67 m³·mol⁻¹	ChemAxon
Polarizability	57.58 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162944863

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione (NP0226868)

MOL for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D MOL for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D SDF for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D-SDF for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

PDB for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D PDB for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

SMILES for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

INCHI for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

Structure for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D Structure for NP0226868 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1-[(2s,4r,5e)-2,4,7-trihydroxy-6-methylhept-5-en-2-yl]-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)