NP-MRD: Showing NP-Card for (3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate (NP0287683)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 16:58:56 UTC

Updated at

2022-09-09 16:58:56 UTC

NP-MRD ID

NP0287683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

Description

(3E,6R)-6-[(1S,2S,7S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,8-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate 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. (3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate is found in Anagallis arvensis. Based on a literature review very few articles have been published on (3E,6R)-6-[(1S,2S,7S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,8-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092218582D          

 40 43  0  0  1  0            999 V2000
   -7.7952    0.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9779    0.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6670    1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4716    0.2340    0.0000 O   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 C   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
   -3.2026    0.6855    0.0000 O   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  1  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  0  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  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  1  0  0  0
 15 12  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 25 34  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 15 39  1  0  0  0  0
 19 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END

     RDKit          3D

 84 87  0  0  0  0  0  0  0  0999 V2000
    9.0508   -1.5804    2.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2209   -0.5031    1.7455 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5013    0.6981    1.9505 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1445   -0.8376    0.9741 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2983    0.0892    0.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6472    0.9675    1.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926    1.0032   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1683   -0.6103   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    0.0569   -0.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332   -0.6603   -1.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -1.9117   -1.5404 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418    0.0639   -2.2889 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3135   -0.1685   -3.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724    1.4519   -2.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677   -0.3290   -2.0029 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2887   -1.7450   -2.2991 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0234   -1.8722   -3.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9365   -2.0454   -1.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3138   -0.6971   -0.8949 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0578   -0.0018   -2.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0741   -0.7295    0.4123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2101   -1.6277    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4124   -1.3328    0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7102   -0.0202    1.3515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7932    1.0375    0.7923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0773    2.2843    1.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3418    2.6266    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7296    3.7853    2.3753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3919    1.8041    1.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4470    2.2964    0.6288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1719    0.3361    1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1093   -0.2882    2.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5089   -0.1071   -0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569    0.6175    0.9312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0983    0.6300    2.4501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4749    1.6309    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8786    2.7801    0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1611    1.3537   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -0.0953   -0.6569 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7285   -0.8154    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6628   -1.8272    3.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9655   -2.4743    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1300   -1.2684    2.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5179    0.4023    2.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2290    1.8889    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542    1.2668    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4860    0.3875   -1.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2325    1.6723   -1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7025    1.6342   -0.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1705   -1.6926   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2691    1.1386   -0.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141   -1.2678   -3.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4847    0.2588   -4.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2826    0.2831   -4.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3527    1.7304   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007    0.2892   -2.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0175   -2.5103   -2.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1975   -2.8495   -3.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -2.4183   -2.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7666   -2.8269   -0.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589   -0.4815   -3.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8838    1.0720   -2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1476   -0.2605   -1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3394   -1.2350    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312   -2.6335   -0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2576   -2.0498    0.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6092   -0.0875    2.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1130    1.2343   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3413    2.9230    2.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3612    4.3974    1.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6592   -1.1104    2.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9926   -0.6594    1.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5001    0.4417    2.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4434    0.4326   -0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6555    0.1285   -1.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7283   -1.1745   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0145   -0.4129    2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8863    1.1116    3.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064    1.1029    2.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0276    2.0032   -1.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6126    1.6467    0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5093   -1.8765    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306   -0.3273    1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452   -0.7296    0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  1  6
 12 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 25 34  1  0
 34 35  1  1
 34 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  0
 39 40  1  1
 39 15  1  0
 39 19  1  0
 34 21  1  0
 31 24  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  6 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  0
  7 48  1  0
  7 49  1  0
  8 50  1  0
  9 51  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 15 56  1  6
 16 57  1  1
 17 58  1  0
 18 59  1  0
 18 60  1  0
 20 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  1
 22 65  1  0
 23 66  1  0
 24 67  1  1
 25 68  1  6
 26 69  1  0
 28 70  1  0
 32 71  1  0
 32 72  1  0
 32 73  1  0
 33 74  1  0
 33 75  1  0
 33 76  1  0
 35 77  1  0
 35 78  1  0
 35 79  1  0
 38 80  1  0
 38 81  1  0
 40 82  1  0
 40 83  1  0
 40 84  1  0
M  END


  Mrv1652309092218582D          

 40 43  0  0  1  0            999 V2000
   -7.7952    0.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9779    0.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6670    1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4716    0.2340    0.0000 O   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 C   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
   -3.2026    0.6855    0.0000 O   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  1  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  0  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  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  1  0  0  0
 15 12  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 25 34  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 15 39  1  0  0  0  0
 19 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0287683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C)(C)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3C=C[C@H]4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10-14,18-19,21-22,25,34-35,39H,15-16H2,1-9H3/b13-12+/t18-,19+,21+,22-,25-,29-,30+,31-,32-/m0/s1

> <INCHI_KEY>
MZTAWCPBCWNTIE-PZFOFYFOSA-N

> <FORMULA>
C32H44O8

> <MOLECULAR_WEIGHT>
556.696

> <EXACT_MASS>
556.303618377

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
61.15236529721683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,6R)-6-[(1S,2S,7S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,8-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

> <JCHEM_LOGP>
3.5269745529999987

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.942899781312434

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.185090896295439

> <JCHEM_PKA_STRONGEST_BASIC>
-2.884108119811378

> <JCHEM_POLAR_SURFACE_AREA>
138.20000000000002

> <JCHEM_REFRACTIVITY>
152.8784

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3E,6R)-6-[(1S,2S,7S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,8-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0     -14.551   1.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.025   1.653   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0     -12.445   3.079   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0     -12.080   0.437   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -10.555   0.648   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.344  -0.878   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.765   2.173   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.029   0.858   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.084  -0.358   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.559  -0.147   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.978   1.280   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.829  -2.308   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.398  -0.418   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.545  -4.581   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.237  -5.472   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.920  -1.258   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.600  -6.094   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.240  -6.586   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.372  -0.445   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -3.801  -1.143   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    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   39                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   39                                             
CONECT   20   19                                                            
CONECT   21   19   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   25   21   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   15   19   40                                             
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
(3E,6R)-6-[(1S,2S,7S,10S,11S,13R,14R,15R)-4,13-Dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0,.0,]heptadeca-3,8-dien-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acid	Generator

Chemical Formula

C₃₂H₄₄O₈

Average Mass

556.6960 Da

Monoisotopic Mass

556.30362 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C)(C)\C=C\C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3C=C[C@H]4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

InChI Identifier

InChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10-14,18-19,21-22,25,34-35,39H,15-16H2,1-9H3/b13-12+/t18-,19+,21+,22-,25-,29-,30+,31-,32-/m0/s1

InChI Key

MZTAWCPBCWNTIE-PZFOFYFOSA-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
Anagallis arvensis	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
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
Steroid ester
2-hydroxysteroid
3-oxo-5-beta-steroid
16-hydroxysteroid
16-alpha-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
3-oxo-delta-1-steroid
Oxosteroid
11-oxosteroid
3-oxosteroid
Delta-1-steroid
Cyclohexenone
Acyloin
Alpha-hydroxy ketone
Cyclic alcohol
Enone
Tertiary alcohol
Alpha,beta-unsaturated ketone
Acryloyl-group
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Enol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen 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

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

163010851

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate (NP0287683)

MOL for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D MOL for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D SDF for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D-SDF for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

PDB for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D PDB for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

SMILES for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

INCHI for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

Structure for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)

3D Structure for NP0287683 ((3e,6r)-6-[(1r,2r,3as,3bs,5as,9as,9bs,11ar)-2,8-dihydroxy-3a,6,6,9b,11a-pentamethyl-7,10-dioxo-1h,2h,3h,3bh,5ah,9ah,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate)