NP-MRD: Showing NP-Card for (2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid (NP0306164)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 22:28:26 UTC

Updated at

2022-09-10 22:28:27 UTC

NP-MRD ID

NP0306164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid

Description

3Alpha,25-Dihydroxytirucalla-8-ene-21-oic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid is found in Ozoroa insignis. Based on a literature review very few articles have been published on 3alpha,25-Dihydroxytirucalla-8-ene-21-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112200282D          

 34 37  0  0  1  0            999 V2000
    8.4474   -2.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5924   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2897   -2.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  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
    5.2939   -0.7929    0.0000 C   0  0  2  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
    4.1657   -1.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  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  2  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  1  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  1  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
  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  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  8  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
M  END

     RDKit          3D

 84 87  0  0  0  0  0  0  0  0999 V2000
    7.4754   -0.9233   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3744   -1.6609   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5929   -1.4405   -2.8434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5028   -3.0244   -1.1261 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9974   -1.1802   -0.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7795   -1.3916    0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163   -0.9260    0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037    0.5233    0.7514 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2773    1.2687    1.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0803    2.0104    0.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4305    1.1708    2.8447 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9212    1.0966    1.1622 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5717    1.0059    2.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851    1.3883    2.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2798    1.6338    1.1818 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0386    3.0570    0.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6262    1.2866    0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8398    0.7811   -0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8066    0.4590   -1.4260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5955    0.7502   -0.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6845    0.6342    0.5077 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1937   -0.7256    0.9230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678    0.5144   -0.7865 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9382    1.8271   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3530   -0.3649   -2.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7701   -0.6327   -2.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7328   -0.5393   -1.2419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7982   -1.4475   -1.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1585   -0.8699    0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1164   -2.4022    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2160   -0.4589    1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8198   -0.2690    0.3826 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8153    0.4656    1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7582    1.5105    1.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4111   -0.8833   -1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1205    0.0969   -0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6093   -1.4718    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1629   -2.2610   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5939   -1.2811   -3.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1535   -0.4919   -2.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3820   -3.2485   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8984   -0.1516   -1.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2690   -1.7929   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5893   -1.0028    1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844   -2.5096    0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3431   -1.1889    2.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985   -1.5414    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3330    0.7181   -0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3289    0.8147    3.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9937    2.2106    0.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    1.7829    3.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6386    0.0087    3.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321    0.6178    3.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0806    2.3295    3.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030    3.6765    0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6132    3.5427    1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    3.1980   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0065    1.0354   -2.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9305   -0.6166   -1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806    1.6769   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -0.0714   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8753   -0.7064    1.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1838   -1.4222    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -1.2181    1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7267    2.0822   -0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2111    2.6914   -0.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301    1.8653   -2.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593    0.1109   -2.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8522   -1.3347   -1.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1279    0.0411   -3.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -1.6667   -2.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2429    0.4643   -1.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2473   -1.2948   -2.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8173   -2.8549   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3194   -2.7307    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0814   -2.7318   -0.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5633    0.5700    0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9288   -0.7251    2.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1004   -1.1184    0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971   -1.1324    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7903    0.9441    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978   -0.2651    2.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3524    1.5932    2.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2299    2.5163    1.5321 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  1  0
  6  7  1  0
  7  8  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 18 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
 21 12  1  0
 32 23  1  0
 21 15  1  0
 34 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
  7 47  1  0
  8 48  1  6
 12 50  1  6
 13 51  1  0
 13 52  1  0
 14 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  0
 20 61  1  0
 22 62  1  0
 22 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 27 72  1  1
 28 73  1  0
 30 74  1  0
 30 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 31 79  1  0
 32 80  1  1
 33 81  1  0
 33 82  1  0
 34 83  1  0
 34 84  1  0
 11 49  1  0
M  END


  Mrv1652309112200282D          

 34 37  0  0  1  0            999 V2000
    8.4474   -2.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5924   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2897   -2.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  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
    5.2939   -0.7929    0.0000 C   0  0  2  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
    4.1657   -1.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  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  2  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  1  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  1  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
  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  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  8  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306164

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O4/c1-26(2,34)15-8-9-19(25(32)33)20-12-17-30(7)22-10-11-23-27(3,4)24(31)14-16-28(23,5)21(22)13-18-29(20,30)6/h19-20,23-24,31,34H,8-18H2,1-7H3,(H,32,33)/t19-,20-,23-,24+,28+,29-,30+/m0/s1

> <INCHI_KEY>
OXLMQAKCNSYPEG-OFOIOPPSSA-N

> <FORMULA>
C30H50O4

> <MOLECULAR_WEIGHT>
474.726

> <EXACT_MASS>
474.37091009

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
57.27580333455644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
5.576862734333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.530761062882938

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.775070104717584

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6744317891171744

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
137.2221

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      15.769  -4.706   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.039  -2.545   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.608  -4.436   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.776  -3.117   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.247  -4.122   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.835   2.854   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   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   34                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   15   22                                             
CONECT   22   21                                                            
CONECT   23   18   24   25   32                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   23   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   17                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3a,25-Dihydroxytirucalla-8-ene-21-Oate	Generator
3a,25-Dihydroxytirucalla-8-ene-21-Oic acid	Generator
3alpha,25-Dihydroxytirucalla-8-ene-21-Oate	Generator
3Α,25-dihydroxytirucalla-8-ene-21-Oate	Generator
3Α,25-dihydroxytirucalla-8-ene-21-Oic acid	Generator

Chemical Formula

C₃₀H₅₀O₄

Average Mass

474.7260 Da

Monoisotopic Mass

474.37091 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H50O4/c1-26(2,34)15-8-9-19(25(32)33)20-12-17-30(7)22-10-11-23-27(3,4)24(31)14-16-28(23,5)21(22)13-18-29(20,30)6/h19-20,23-24,31,34H,8-18H2,1-7H3,(H,32,33)/t19-,20-,23-,24+,28+,29-,30+/m0/s1

InChI Key

OXLMQAKCNSYPEG-OFOIOPPSSA-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
Ozoroa insignis	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
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Steroid
Medium-chain hydroxy acid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
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	5.58	ChemAxon
pKa (Strongest Acidic)	4.78	ChemAxon
pKa (Strongest Basic)	-0.67	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	137.22 m³·mol⁻¹	ChemAxon
Polarizability	57.28 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102253060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid (NP0306164)

MOL for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

3D MOL for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

3D SDF for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

3D-SDF for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

PDB for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

3D PDB for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

SMILES for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

INCHI for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

Structure for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)

3D Structure for NP0306164 ((2s)-2-[(1s,3as,5ar,7r,9as,11as)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-hydroxy-6-methylheptanoic acid)