NP-MRD: Showing NP-Card for (2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid (NP0278094)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 03:00:07 UTC

Updated at

2022-09-09 03:00:07 UTC

NP-MRD ID

NP0278094

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid

Description

Triptohypol C, also known as dihydrocelastrol, belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. Triptohypol C is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid is found in Tripterygium hypoglaucum. (2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid was first documented in 2010 (PMID: 20167482). Based on a literature review a small amount of articles have been published on triptohypol C (PMID: 21570383) (PMID: 25139619).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205002D          

 33 37  0  0  1  0            999 V2000
    4.1763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1390   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2205   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8525   -4.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4453   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2388   -2.7770    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 27 26  1  1  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 73 77  0  0  0  0  0  0  0  0999 V2000
    6.0755    0.7973   -1.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2275   -0.1974   -1.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -1.5201   -1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7631   -1.9281   -1.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8049   -2.4297   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1898   -3.7627   -0.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642   -2.0297    0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744   -0.6918    0.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0775    0.2046   -0.3313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137    1.6271   -0.3193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576    1.8324   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628    0.9710    0.5086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0061    1.2857    0.6617 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2473    1.7290    2.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4745    2.3414   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    2.5985   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8350    1.4415   -0.0369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9655    1.8616    0.9284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635    1.3408   -1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6384    0.3233   -1.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2515   -0.9823   -0.6928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2348   -1.4050    0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3954   -2.0321   -1.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6704   -1.7309   -2.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -3.3545   -1.3713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651   -1.0738   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537    0.1551    0.4092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7607    0.0340    0.2911 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2903   -0.3718   -1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263   -1.1288    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259   -1.4530    1.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477   -0.2607    1.0468 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4906   -0.0940    2.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0960    1.7087   -1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6598    1.1091   -2.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1084    0.4142   -1.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9902   -2.9141   -1.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6476   -4.4815    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -2.7415    0.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201    2.1498    0.4530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0224    2.0535   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8640    2.7599   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406    1.6660    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142    2.8057    2.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590    1.1933    2.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2140    2.1007   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0380    3.3183   -0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0283    3.2676    0.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2287    3.2988   -0.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5783    2.6611    1.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2214    1.0225    1.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8152    2.3130    0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8972    1.2726   -2.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0773    2.3458   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0755    0.2053   -2.3256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4771    0.7401   -0.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5340   -2.4529    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7087   -1.3171    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1309   -0.7637    0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9506   -3.6279   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950   -1.4412   -0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8836   -1.9086    0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    0.0922    1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7431    0.0427   -1.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1764   -1.4668   -1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9117   -0.0169   -1.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6403   -0.9669    2.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8742   -2.0308    0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005   -2.1389    1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874   -2.0061    0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873   -0.4277    3.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294   -0.8255    2.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9050    0.8901    2.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 32  1  0
 32 33  1  1
 32 31  1  0
 31 30  1  0
 30 28  1  0
 28 29  1  6
 28 27  1  0
 27 26  1  0
 26 21  1  0
 21 22  1  0
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  1
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  1
 21 23  1  6
 23 25  1  0
 23 24  2  0
  9  2  1  0
 13 12  1  0
 32  8  1  0
 13 28  1  0
 17 27  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  6 38  1  0
  7 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 33 71  1  0
 33 72  1  0
 33 73  1  0
 31 69  1  0
 31 70  1  0
 30 67  1  0
 30 68  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 27 63  1  1
 26 61  1  0
 26 62  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 20 55  1  0
 20 56  1  0
 19 53  1  0
 19 54  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
 16 48  1  0
 16 49  1  0
 15 46  1  0
 15 47  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 25 60  1  0
M  END


  Mrv1652309092205002D          

 33 37  0  0  1  0            999 V2000
    4.1763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3513   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1390   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2205   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8525   -4.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4453   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2388   -2.7770    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  1  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 27 26  1  1  0  0  0
 17 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 12 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0278094

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(O)=CC2=C1CC=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@@](C)(CC[C@]3(C)CC[C@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h8,15,22,30-31H,7,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1

> <INCHI_KEY>
WZAUFGYINZYCKH-JJWQIEBTSA-N

> <FORMULA>
C29H40O4

> <MOLECULAR_WEIGHT>
452.635

> <EXACT_MASS>
452.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.245539663176956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4aS,6aS,12bS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6,6a,8,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

> <JCHEM_LOGP>
6.903507442

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.462475319148417

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.73994629112054

> <JCHEM_PKA_STRONGEST_BASIC>
-6.279744606500988

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
131.5255

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4aS,6aS,12bS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1H-picene-2-carboxylic acid

> <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       7.796  -1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.256  -3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.796  -6.517   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.876  -1.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.956  -1.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.576  -1.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.793  -5.710   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.078  -6.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      20.258  -7.690   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      17.631  -7.227   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.266  -5.184   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.646  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   32                                                  
CONECT   13   12   14   15   28                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   27                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26   17   28                                                  
CONECT   28   27   13   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   12    8   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Dihydrocelastrol	ChEBI

Chemical Formula

C₂₉H₄₀O₄

Average Mass

452.6350 Da

Monoisotopic Mass

452.29266 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(O)=CC2=C1CC=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@@](C)(CC[C@]3(C)CC[C@]12C)C(O)=O

InChI Identifier

InChI=1S/C29H40O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h8,15,22,30-31H,7,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1

InChI Key

WZAUFGYINZYCKH-JJWQIEBTSA-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
Tripterygium hypoglaucum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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

8587010

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10411574

PDB ID

Not Available

ChEBI ID

132340

Good Scents ID

Not Available

References

General References

Ryu YB, Park SJ, Kim YM, Lee JY, Seo WD, Chang JS, Park KH, Rho MC, Lee WS: SARS-CoV 3CLpro inhibitory effects of quinone-methide triterpenes from Tripterygium regelii. Bioorg Med Chem Lett. 2010 Mar 15;20(6):1873-6. doi: 10.1016/j.bmcl.2010.01.152. Epub 2010 Feb 4. [PubMed:20167482 ]
Seo HR, Seo WD, Pyun BJ, Lee BW, Jin YB, Park KH, Seo EK, Lee YJ, Lee YS: Radiosensitization by celastrol is mediated by modification of antioxidant thiol molecules. Chem Biol Interact. 2011 Aug 15;193(1):34-42. doi: 10.1016/j.cbi.2011.04.009. Epub 2011 May 4. [PubMed:21570383 ]
Fribley AM, Miller JR, Brownell AL, Garshott DM, Zeng Q, Reist TE, Narula N, Cai P, Xi Y, Callaghan MU, Kodali V, Kaufman RJ: Celastrol induces unfolded protein response-dependent cell death in head and neck cancer. Exp Cell Res. 2015 Jan 15;330(2):412-422. doi: 10.1016/j.yexcr.2014.08.014. Epub 2014 Aug 17. [PubMed:25139619 ]
LOTUS database [Link]

Showing NP-Card for (2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid (NP0278094)

MOL for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

3D MOL for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

3D SDF for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

3D-SDF for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

PDB for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

3D PDB for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

SMILES for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

INCHI for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

Structure for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)

3D Structure for NP0278094 ((2r,4as,6as,12bs,14as,14br)-10,11-dihydroxy-2,4a,6a,9,12b,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1h-picene-2-carboxylic acid)