NP-MRD: Showing NP-Card for (1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione (NP0183772)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 22:44:09 UTC

Updated at

2022-09-03 22:44:09 UTC

NP-MRD ID

NP0183772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1R,2R,4S,10S,11S,13R,14R,15R)-14-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[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)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione is found in Bryonia alba. Based on a literature review very few articles have been published on (1R,2R,4S,10S,11S,13R,14R,15R)-14-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200442D          

 36 39  0  0  1  0            999 V2000
   -6.4716    0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -0.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672    1.1641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8371    0.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307   -0.1916    0.0000 C   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
   -3.6585   -1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
 11  8  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 21 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END

     RDKit          3D

 82 85  0  0  0  0  0  0  0  0999 V2000
    7.7885    0.4637    0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1478    0.5177    1.8530 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6554   -0.7015    2.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5172    1.6889    2.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6754    0.4413    1.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0194    1.0643    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5437    0.9133    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332    0.3044   -0.7286 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7258   -1.0481   -0.9344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167    1.1484   -1.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.4979   -1.0859 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4912   -0.1488   -2.4459 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6347    0.7440   -3.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070   -0.7623   -2.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258   -0.0582   -1.2518 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8848    1.3343   -1.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7126   -0.8034   -0.6987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6572   -1.1736   -1.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588   -1.2915   -1.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4944   -0.4179   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5378    0.6219    0.0599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0752    1.5105    1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4981    1.8767    0.7936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9718    2.8625    1.6509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2949    0.6146    0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2159    0.5830    1.6947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9106   -0.5230    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8450   -0.4890   -1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1736   -1.8435    0.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2834   -0.1083    0.4871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7872   -1.1486    1.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2953    0.7443    1.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6924    1.3377    2.1880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1148    0.9481    0.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6275   -0.0141   -0.2308 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8237   -1.3289    0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2495    1.4622    0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6007   -0.2695    0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0466    0.1950   -0.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0115   -0.9960    3.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7013   -0.4793    2.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7545   -1.5777    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8317    2.3121    1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1326   -0.1856    2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5949    1.6687    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2365    0.3227    1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1436    1.9540    0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4436   -1.1082   -1.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0433   -1.8802   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3845   -1.3602   -0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6152    2.0932   -1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5801    1.6222   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1930   -0.9751   -2.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1375    1.5368   -3.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4074   -0.4521   -3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1509   -1.8665   -2.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6937    1.2648   -2.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0453    1.8019   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121    2.0315   -0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802   -1.7792   -0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006   -0.4686   -2.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -2.1908   -2.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7262   -2.0768   -1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    1.2732   -0.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4579    2.4345    1.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133    1.1098    2.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5166    2.2012   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9268    3.7477    1.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8903   -1.5202   -1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8393   -0.2377   -0.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4846    0.2156   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2806   -2.4996    0.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0692   -2.3510    0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3080   -1.6595    1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0103   -1.2722    2.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547   -0.8804    1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884   -2.1300    1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211    0.7338    1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    2.0032    0.5675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092   -1.4316    0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7085   -2.2032   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1094   -1.4983    1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  6
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 21 30  1  0
 30 31  1  1
 30 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  1
 35 11  1  0
 35 15  1  0
 30 17  1  0
 27 20  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  6 45  1  0
  7 46  1  0
  7 47  1  0
  9 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 11 52  1  6
 12 53  1  6
 13 54  1  0
 14 55  1  0
 14 56  1  0
 16 57  1  0
 16 58  1  0
 16 59  1  0
 17 60  1  1
 18 61  1  0
 18 62  1  0
 19 63  1  0
 21 64  1  6
 22 65  1  0
 22 66  1  0
 23 67  1  6
 24 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
 29 74  1  0
 31 75  1  0
 31 76  1  0
 31 77  1  0
 34 78  1  0
 34 79  1  0
 36 80  1  0
 36 81  1  0
 36 82  1  0
M  END


  Mrv1652309042200442D          

 36 39  0  0  1  0            999 V2000
   -6.4716    0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -0.4703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672    1.1641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8371    0.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307   -0.1916    0.0000 C   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
   -3.6585   -1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
 11  8  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 21 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0183772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)\C=C\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/C30H46O6/c1-25(2,35)12-9-13-29(7,36)23-20(32)15-27(5)21-11-10-17-18(14-19(31)24(34)26(17,3)4)30(21,8)22(33)16-28(23,27)6/h9-10,12,18-21,23,31-32,35-36H,11,13-16H2,1-8H3/b12-9+/t18-,19+,20-,21+,23+,27+,28-,29+,30+/m1/s1

> <INCHI_KEY>
IJFYQSUPMMVTOA-NZKKDQNNSA-N

> <FORMULA>
C30H46O6

> <MOLECULAR_WEIGHT>
502.692

> <EXACT_MASS>
502.329439201

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.66515708195445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.8435903439999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.44124838712823

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.325214792560246

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5822758630899574

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
141.37589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0     -12.080   0.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.555   0.648   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.344  -0.878   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -10.765   2.173   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -9.029   0.858   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.084  -0.358   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.559  -0.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.829  -2.308   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.398  -0.418   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.545  -4.581   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.237  -5.472   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.920  -1.258   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.600  -6.094   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.240  -6.586   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.372  -0.445   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   35                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   35                                             
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   21   17   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   11   15   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₆

Average Mass

502.6920 Da

Monoisotopic Mass

502.32944 Da

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

CC(C)(O)\C=C\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/C30H46O6/c1-25(2,35)12-9-13-29(7,36)23-20(32)15-27(5)21-11-10-17-18(14-19(31)24(34)26(17,3)4)30(21,8)22(33)16-28(23,27)6/h9-10,12,18-21,23,31-32,35-36H,11,13-16H2,1-8H3/b12-9+/t18-,19+,20-,21+,23+,27+,28-,29+,30+/m1/s1

InChI Key

IJFYQSUPMMVTOA-NZKKDQNNSA-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
Bryonia alba	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
25-hydroxysteroid
20-hydroxysteroid
3-oxo-delta-5-steroid
3-oxosteroid
14-alpha-methylsteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
2-hydroxysteroid
Oxosteroid
11-oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Cyclic ketone
Ketone
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
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	2.84	ChemAxon
pKa (Strongest Acidic)	13.33	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.38 m³·mol⁻¹	ChemAxon
Polarizability	56.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Rule of Five	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

10244882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12114146

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)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione (NP0183772)

MOL for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D MOL for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D SDF for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D-SDF for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

PDB for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D PDB for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

SMILES for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

INCHI for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

Structure for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D Structure for NP0183772 ((1r,2r,3as,3bs,8s,9ar,9br,11ar)-1-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,8h,9h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)