NP-MRD: Showing NP-Card for marianine (NP0238993)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 22:29:27 UTC

Updated at

2022-09-06 22:29:27 UTC

NP-MRD ID

NP0238993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

marianine

Description

Marianine belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. marianine is found in Silybum marianum. marianine was first documented in 2006 (PMID: 16394559). Based on a literature review very few articles have been published on marianine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072200292D          

 34 37  0  0  1  0            999 V2000
    4.3612   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -2.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6848   -3.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -4.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0335   -4.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3361   -3.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  6  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  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  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  2  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
M  END

     RDKit          3D

 84 87  0  0  0  0  0  0  0  0999 V2000
    5.2661   -2.0563   -0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7748   -0.8397    0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0436   -0.0383    1.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2006    1.0895    0.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748    0.8492    0.0525 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2889    0.2191   -1.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8722    0.1636    0.8090 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6313    0.8430    2.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1330    0.8911    2.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.0708    1.3137 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0486   -1.4577    1.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357    0.0753    0.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888    0.2053   -0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    0.0708   -1.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1941   -0.4102   -1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459    0.3680    0.1683 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3434    1.8448   -0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5271    0.5146   -0.5780 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8225    1.8450    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7854    0.6781   -2.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2796    0.9414   -2.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9712   -0.3275   -1.8333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3442   -0.1230   -1.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6740   -0.8306   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465   -2.3464   -0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618   -0.2899    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2997   -0.6171    0.0367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2020   -0.4230    1.5375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8594    0.0851    1.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072    0.5426    3.0308 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0746   -0.5320   -0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1804   -0.4459    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1363    0.6609   -1.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4784   -1.6234   -1.1272 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -2.3542    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7188   -2.7200   -0.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7960    0.2942    2.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -0.7310    1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185    1.7994    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9987    1.7250    1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    1.8956   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3859    0.2653   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0049   -0.8592   -1.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8499    0.7743   -2.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581   -0.8984    0.9277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0213    1.8529    2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0833    0.1811    2.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1698    0.5593    3.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2853    1.9147    2.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228   -1.9616    1.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5011   -2.0812    1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -1.4627    2.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0289    1.0705   -1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -0.5921   -2.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552   -1.4916   -0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8194   -0.3338   -1.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    2.1782    0.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7680    2.1180   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8803    2.4804    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7240    1.8299    0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9782    2.6638   -0.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015    2.2273    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2730    1.6125   -2.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5342   -0.1955   -2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586    1.2156   -3.2185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6184    1.7388   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6893   -1.0967   -2.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7833   -0.8272   -2.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5801   -2.7380   -1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4481   -2.8769    0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0613   -2.5158   -0.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7274   -0.7389    1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8645    0.7928    0.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7248   -0.6924    0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7036   -1.5553   -0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9977    0.2263    1.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3716   -1.4385    1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3640    0.6129    1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1481   -0.8236    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9266   -1.0833    1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5987    0.4666   -2.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9136    1.6230   -0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2158    0.7855   -1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9796   -2.2916   -0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 13 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 16  7  1  0
 27 18  1  0
 16 10  1  0
 29 12  1  0
  6 42  1  0
  6 43  1  0
  6 44  1  0
  5 41  1  6
  4 39  1  0
  4 40  1  0
  3 37  1  0
  3 38  1  0
  1 35  1  0
  1 36  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  0
 33 82  1  0
 33 83  1  0
 34 84  1  0
  7 45  1  1
  8 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 11 50  1  0
 11 51  1  0
 11 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 17 57  1  0
 17 58  1  0
 17 59  1  0
 19 60  1  0
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 21 65  1  0
 21 66  1  0
 22 67  1  6
 23 68  1  0
 25 69  1  0
 25 70  1  0
 25 71  1  0
 26 72  1  0
 26 73  1  0
 26 74  1  0
 27 75  1  1
 28 76  1  0
 28 77  1  0
M  END


  Mrv1652309072200292D          

 34 37  0  0  1  0            999 V2000
    4.3612   -3.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -2.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6848   -3.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -4.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0335   -4.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3361   -3.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  6  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  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  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 29 30  2  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238993

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(=C)C(C)(C)O)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O3/c1-19(10-11-20(2)28(5,6)34)21-12-17-31(9)26-22(13-16-30(21,31)8)29(7)15-14-25(33)27(3,4)24(29)18-23(26)32/h19,21,24-25,33-34H,2,10-18H2,1,3-9H3/t19-,21-,24+,25+,29-,30-,31+/m1/s1

> <INCHI_KEY>
UVPFSDRHWXKUSF-FRIHGVDDSA-N

> <FORMULA>
C31H50O3

> <MOLECULAR_WEIGHT>
470.738

> <EXACT_MASS>
470.37599547

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
57.72155855125692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,11R,14R,15R)-5-hydroxy-14-[(2R)-6-hydroxy-6-methyl-5-methylideneheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-9-one

> <JCHEM_LOGP>
6.069134701333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.618725644141033

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.33357663514251

> <JCHEM_PKA_STRONGEST_BASIC>
-0.67335933256187

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
140.3961

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,11R,14R,15R)-5-hydroxy-14-[(2R)-6-hydroxy-6-methyl-5-methylideneheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       8.141  -5.759   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.666  -5.549   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.247  -4.122   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.612  -6.765   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.557  -7.980   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.396  -7.710   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.827  -5.819   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13   29                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    7   10   17                                             
CONECT   17   16                                                            
CONECT   18   13   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   12   30                                                  
CONECT   30   29                                                            
CONECT   31    2   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
24-Methylene-7-oxo-lanosta-8(9)-3beta,25-diol	ChEBI
24-Methylene-7-oxo-lanosta-8(9)-3b,25-diol	Generator
24-Methylene-7-oxo-lanosta-8(9)-3β,25-diol	Generator

Chemical Formula

C₃₁H₅₀O₃

Average Mass

470.7380 Da

Monoisotopic Mass

470.37600 Da

IUPAC Name

(2S,5S,7R,11R,14R,15R)-5-hydroxy-14-[(2R)-6-hydroxy-6-methyl-5-methylideneheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-9-one

Traditional Name

(2S,5S,7R,11R,14R,15R)-5-hydroxy-14-[(2R)-6-hydroxy-6-methyl-5-methylideneheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-9-one

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(=C)C(C)(C)O)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3=O

InChI Identifier

InChI=1S/C31H50O3/c1-19(10-11-20(2)28(5,6)34)21-12-17-31(9)26-22(13-16-30(21,31)8)29(7)15-14-25(33)27(3,4)24(29)18-23(26)32/h19,21,24-25,33-34H,2,10-18H2,1,3-9H3/t19-,21-,24+,25+,29-,30-,31+/m1/s1

InChI Key

UVPFSDRHWXKUSF-FRIHGVDDSA-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
Silybum marianum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
25-hydroxysteroid
3-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxysteroid
7-oxosteroid
14-alpha-methylsteroid
Steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Organooxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:66673 )
secondary alcohol (CHEBI:66673 )
tetracyclic triterpenoid (CHEBI:66673 )
cyclic terpene ketone (CHEBI:66673 )

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	6.07	ChemAxon
pKa (Strongest Acidic)	18.33	ChemAxon
pKa (Strongest Basic)	-0.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	140.4 m³·mol⁻¹	ChemAxon
Polarizability	57.72 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

C00051487

Chemspider ID

9743791

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11569021

PDB ID

Not Available

ChEBI ID

66673

Good Scents ID

Not Available

References

General References

Ahmed E, Malik A, Ferheen S, Afza N, Azhar-Ul-Haq, Lodhi MA, Choudhary MI: Chymotrypsin inhibitory triterpenoids from Silybum marianum. Chem Pharm Bull (Tokyo). 2006 Jan;54(1):103-6. doi: 10.1248/cpb.54.103. [PubMed:16394559 ]
LOTUS database [Link]

Showing NP-Card for marianine (NP0238993)

MOL for NP0238993 (marianine)

3D MOL for NP0238993 (marianine)

3D SDF for NP0238993 (marianine)

3D-SDF for NP0238993 (marianine)

PDB for NP0238993 (marianine)

3D PDB for NP0238993 (marianine)

SMILES for NP0238993 (marianine)

INCHI for NP0238993 (marianine)

Structure for NP0238993 (marianine)

3D Structure for NP0238993 (marianine)