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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:43 UTC

Update Date

2022-03-07 02:52:25 UTC

HMDB ID

HMDB0030094

Secondary Accession Numbers

HMDB30094

Metabolite Identification

Common Name

Betulinic acid

Description

Betulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652309272007272D          

 37 41  0  0  0  0            999 V2000
    3.6852  -11.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3962  -11.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1029  -11.8460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8140  -13.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5283  -12.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8114  -11.4345    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5295  -11.8455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5294  -10.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076  -10.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2474  -10.6117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2417  -11.4370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9535  -11.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6726  -11.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9608  -10.1949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3001  -10.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9642   -9.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1389   -9.3890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9708  -13.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0957  -11.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5226  -11.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2422   -9.7862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8071  -12.2554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9578  -11.0145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5922   -8.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8561   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7858   -8.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2339  -12.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6770  -10.6170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3847  -11.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3863  -11.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0979  -10.6141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1086  -13.3822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6809  -12.6694    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1096  -12.6694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8790  -13.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216  -13.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951  -13.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17 14  1  0  0  0  0
  3  2  1  0  0  0  0
  6  9  1  0  0  0  0
  3 19  1  1  0  0  0
  7 11  1  0  0  0  0
  7 20  1  1  0  0  0
 10  8  1  0  0  0  0
 10 21  1  1  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
  6 22  1  6  0  0  0
  1  2  1  0  0  0  0
 14 23  1  6  0  0  0
 17 24  1  6  0  0  0
  3  6  1  0  0  0  0
 24 25  2  0  0  0  0
 10 14  1  0  0  0  0
 24 26  1  0  0  0  0
 11 12  1  0  0  0  0
 11 27  1  6  0  0  0
 12 13  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  6  7  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 28 29  1  1  0  0  0
 13 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 15  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 34 32  1  6  0  0  0
 37 35  1  0  0  0  0
 37 36  1  0  0  0  0
 33 37  1  0  0  0  0
 37 34  1  0  0  0  0
 33 18  1  1  0  0  0
  1 33  1  0  0  0  0
  3 34  1  0  0  0  0
 34  4  1  0  0  0  0
M  END

HMDB0030094
     RDKit          3D
Betulinic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -3.8962    2.1376    2.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1699    1.0124    2.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5051   -0.1853    2.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1237    1.0477    0.5173 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4615    0.4428    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0998   -0.8728   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547   -0.4405   -1.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9738    0.5878   -2.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6491    1.7714   -2.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109    0.2378   -3.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714   -1.6084   -1.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5019   -1.4872   -1.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9141   -0.6859   -0.6217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8382   -1.5606    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7639    0.5604   -0.3107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1802    1.3249    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798    1.6124    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0356    0.4303    0.2677 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5349    0.6422    0.2252 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9736    1.7376   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201    1.0314    1.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919    0.9438    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8979   -0.4162    1.5556 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2883   -0.4622    1.7639 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693   -0.8581    0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4630   -0.1919   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727   -2.3653    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -0.7069   -0.1022 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7138   -1.1153   -1.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372   -1.2231   -1.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -0.1137   -1.0067 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2472    0.9516   -2.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    0.0718    0.0144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9271    2.1424    3.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    3.0657    2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535   -0.1230    3.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384   -1.1464    2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5764   -0.2394    3.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9941    2.0586    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234    0.1889    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877    1.1309   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8074   -1.1260   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857   -1.6261    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.6528   -3.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269   -1.8415   -2.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3198   -2.4992   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0852   -2.5354   -1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694   -1.1947   -2.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -1.0483    1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0847   -2.2023    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -2.3170    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584    1.2072   -1.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391    0.9010    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869    2.3366    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033    2.5636    0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    1.7986    1.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871   -0.3824    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8708    2.2452   -0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    1.4249   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    2.5443   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6401    2.1199    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3653    0.4680    2.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    1.7645    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5341    1.0744    3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583   -1.1439    2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6468    0.4775    1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -0.1845   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7718    0.8070   -0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4230   -0.7880   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0679   -2.8838    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062   -2.4980    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9585   -2.7303   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876   -1.4316    0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357   -2.1529   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219   -0.5057   -2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0006   -1.2475   -2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   -2.2465   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767    1.9542   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897    0.9750   -2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    0.7403   -2.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034   -0.7978    0.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 15 33  1  0
 33  4  1  0
 33  7  1  0
 31 13  1  0
 31 18  1  0
 28 19  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  1
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  6
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  1
 20 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  1
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  1
M  END


  Mrv1652309272007272D          

 37 41  0  0  0  0            999 V2000
    3.6852  -11.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3962  -11.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1029  -11.8460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8140  -13.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5283  -12.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8114  -11.4345    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5295  -11.8455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5294  -10.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076  -10.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2474  -10.6117    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2417  -11.4370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9535  -11.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6726  -11.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9608  -10.1949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.3001  -10.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9642   -9.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1389   -9.3890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9708  -13.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0957  -11.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5226  -11.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2422   -9.7862    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8071  -12.2554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9578  -11.0145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5922   -8.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8561   -7.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7858   -8.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2339  -12.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6770  -10.6170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3847  -11.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3863  -11.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0979  -10.6141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1086  -13.3822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6809  -12.6694    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1096  -12.6694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8790  -13.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9216  -13.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3951  -13.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17 14  1  0  0  0  0
  3  2  1  0  0  0  0
  6  9  1  0  0  0  0
  3 19  1  1  0  0  0
  7 11  1  0  0  0  0
  7 20  1  1  0  0  0
 10  8  1  0  0  0  0
 10 21  1  1  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
  6 22  1  6  0  0  0
  1  2  1  0  0  0  0
 14 23  1  6  0  0  0
 17 24  1  6  0  0  0
  3  6  1  0  0  0  0
 24 25  2  0  0  0  0
 10 14  1  0  0  0  0
 24 26  1  0  0  0  0
 11 12  1  0  0  0  0
 11 27  1  6  0  0  0
 12 13  1  0  0  0  0
  4  5  1  0  0  0  0
  5  7  1  0  0  0  0
  6  7  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 28 29  1  1  0  0  0
 13 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 15  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 34 32  1  6  0  0  0
 37 35  1  0  0  0  0
 37 36  1  0  0  0  0
 33 37  1  0  0  0  0
 37 34  1  0  0  0  0
 33 18  1  1  0  0  0
  1 33  1  0  0  0  0
  3 34  1  0  0  0  0
 34  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030094

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
QGJZLNKBHJESQX-FZFNOLFKSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.66739480202057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

> <ALOGPS_LOGP>
5.34

> <JCHEM_LOGP>
6.639739080000002

> <ALOGPS_LOGS>
-6.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.48943339017772

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.748313577998887

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351229684482065

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
132.6255

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030094
     RDKit          3D
Betulinic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -3.8962    2.1376    2.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1699    1.0124    2.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5051   -0.1853    2.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1237    1.0477    0.5173 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4615    0.4428    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0998   -0.8728   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547   -0.4405   -1.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9738    0.5878   -2.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6491    1.7714   -2.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109    0.2378   -3.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714   -1.6084   -1.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5019   -1.4872   -1.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9141   -0.6859   -0.6217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8382   -1.5606    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7639    0.5604   -0.3107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1802    1.3249    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798    1.6124    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0356    0.4303    0.2677 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5349    0.6422    0.2252 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9736    1.7376   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201    1.0314    1.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919    0.9438    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8979   -0.4162    1.5556 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2883   -0.4622    1.7639 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693   -0.8581    0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4630   -0.1919   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727   -2.3653    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -0.7069   -0.1022 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7138   -1.1153   -1.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372   -1.2231   -1.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -0.1137   -1.0067 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2472    0.9516   -2.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    0.0718    0.0144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9271    2.1424    3.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    3.0657    2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535   -0.1230    3.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384   -1.1464    2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5764   -0.2394    3.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9941    2.0586    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234    0.1889    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877    1.1309   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8074   -1.1260   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857   -1.6261    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.6528   -3.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269   -1.8415   -2.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3198   -2.4992   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0852   -2.5354   -1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694   -1.1947   -2.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -1.0483    1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0847   -2.2023    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -2.3170    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584    1.2072   -1.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391    0.9010    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869    2.3366    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033    2.5636    0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    1.7986    1.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871   -0.3824    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8708    2.2452   -0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    1.4249   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    2.5443   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6401    2.1199    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3653    0.4680    2.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    1.7645    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5341    1.0744    3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583   -1.1439    2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6468    0.4775    1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -0.1845   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7718    0.8070   -0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4230   -0.7880   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0679   -2.8838    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062   -2.4980    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9585   -2.7303   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876   -1.4316    0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357   -2.1529   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219   -0.5057   -2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0006   -1.2475   -2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   -2.2465   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767    1.9542   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897    0.9750   -2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    0.7403   -2.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034   -0.7978    0.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 15 33  1  0
 33  4  1  0
 33  7  1  0
 31 13  1  0
 31 18  1  0
 28 19  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  1
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  6
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  1
 20 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  1
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  1
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       6.879 -22.112   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.206 -21.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.525 -22.112   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.853 -24.417   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.186 -23.645   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.848 -21.344   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.188 -22.112   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.188 -19.026   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.841 -19.804   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.528 -19.808   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.518 -21.349   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.847 -22.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.189 -21.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.860 -19.030   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.360 -18.789   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.733 -17.370   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.193 -17.526   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.545 -24.423   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.512 -20.576   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.175 -20.568   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      13.519 -18.268   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      10.840 -22.877   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      14.855 -20.560   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      14.172 -16.373   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.665 -14.913   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.667 -16.673   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.503 -22.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.197 -19.818   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.518 -20.576   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.521 -22.112   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      18.849 -19.813   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       9.536 -24.980   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0       6.871 -23.650   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.538 -23.650   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.241 -25.621   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.187 -25.603   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.204 -24.419   0.000  0.00  0.00           C+0
CONECT    1    2   33                                                       
CONECT    2    3    1                                                       
CONECT    3    2   19    6   34                                             
CONECT    4    5   34                                                       
CONECT    5    4    7                                                       
CONECT    6    9   22    3    7                                             
CONECT    7   11   20    5    6                                             
CONECT    8   10    9                                                       
CONECT    9    6    8                                                       
CONECT   10    8   21   11   14                                             
CONECT   11    7   10   12   27                                             
CONECT   12   11   13                                                       
CONECT   13   12   28                                                       
CONECT   14   17   23   10   28                                             
CONECT   15   16   28                                                       
CONECT   16   15   17                                                       
CONECT   17   14   24   16                                                  
CONECT   18   33                                                            
CONECT   19    3                                                            
CONECT   20    7                                                            
CONECT   21   10                                                            
CONECT   22    6                                                            
CONECT   23   14                                                            
CONECT   24   17   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   11                                                            
CONECT   28   29   13   14   15                                             
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   34                                                            
CONECT   33   37   18    1                                                  
CONECT   34   32   37    3    4                                             
CONECT   35   37                                                            
CONECT   36   37                                                            
CONECT   37   35   36   33   34                                             
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

COMPND    HMDB0030094
HETATM    1  C1  UNL     1      -3.896   2.138   2.655  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.170   1.012   2.006  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.505  -0.185   2.784  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.124   1.048   0.517  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.462   0.443   0.057  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.100  -0.873  -0.648  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.755  -0.440  -1.252  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.974   0.588  -2.270  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.649   1.771  -2.169  1.00  0.00           O  
HETATM   10  O2  UNL     1      -4.611   0.238  -3.487  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.971  -1.608  -1.724  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.502  -1.487  -1.724  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.914  -0.686  -0.622  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.838  -1.561   0.605  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.764   0.560  -0.311  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.180   1.325   0.842  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.280   1.612   0.753  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.036   0.430   0.268  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.535   0.642   0.225  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.974   1.738  -0.667  1.00  0.00           C  
HETATM   21  C19 UNL     1       2.920   1.031   1.658  1.00  0.00           C  
HETATM   22  C20 UNL     1       4.392   0.944   1.893  1.00  0.00           C  
HETATM   23  C21 UNL     1       4.898  -0.416   1.556  1.00  0.00           C  
HETATM   24  O3  UNL     1       6.288  -0.462   1.764  1.00  0.00           O  
HETATM   25  C22 UNL     1       4.569  -0.858   0.161  1.00  0.00           C  
HETATM   26  C23 UNL     1       5.463  -0.192  -0.842  1.00  0.00           C  
HETATM   27  C24 UNL     1       4.873  -2.365   0.111  1.00  0.00           C  
HETATM   28  C25 UNL     1       3.116  -0.707  -0.102  1.00  0.00           C  
HETATM   29  C26 UNL     1       2.714  -1.115  -1.490  1.00  0.00           C  
HETATM   30  C27 UNL     1       1.237  -1.223  -1.614  1.00  0.00           C  
HETATM   31  C28 UNL     1       0.459  -0.114  -1.007  1.00  0.00           C  
HETATM   32  C29 UNL     1       0.247   0.952  -2.051  1.00  0.00           C  
HETATM   33  C30 UNL     1      -3.114   0.072   0.014  1.00  0.00           C  
HETATM   34  H1  UNL     1      -3.927   2.142   3.733  1.00  0.00           H  
HETATM   35  H2  UNL     1      -3.639   3.066   2.150  1.00  0.00           H  
HETATM   36  H3  UNL     1      -3.953  -0.123   3.768  1.00  0.00           H  
HETATM   37  H4  UNL     1      -4.238  -1.146   2.358  1.00  0.00           H  
HETATM   38  H5  UNL     1      -5.576  -0.239   3.071  1.00  0.00           H  
HETATM   39  H6  UNL     1      -3.994   2.059   0.138  1.00  0.00           H  
HETATM   40  H7  UNL     1      -6.123   0.189   0.882  1.00  0.00           H  
HETATM   41  H8  UNL     1      -5.988   1.131  -0.622  1.00  0.00           H  
HETATM   42  H9  UNL     1      -5.807  -1.126  -1.434  1.00  0.00           H  
HETATM   43  H10 UNL     1      -4.886  -1.626   0.105  1.00  0.00           H  
HETATM   44  H11 UNL     1      -5.549   0.653  -3.589  1.00  0.00           H  
HETATM   45  H12 UNL     1      -3.327  -1.841  -2.769  1.00  0.00           H  
HETATM   46  H13 UNL     1      -3.320  -2.499  -1.131  1.00  0.00           H  
HETATM   47  H14 UNL     1      -1.085  -2.535  -1.611  1.00  0.00           H  
HETATM   48  H15 UNL     1      -1.169  -1.195  -2.750  1.00  0.00           H  
HETATM   49  H16 UNL     1      -0.971  -1.048   1.555  1.00  0.00           H  
HETATM   50  H17 UNL     1       0.085  -2.202   0.598  1.00  0.00           H  
HETATM   51  H18 UNL     1      -1.678  -2.317   0.548  1.00  0.00           H  
HETATM   52  H19 UNL     1      -1.758   1.207  -1.180  1.00  0.00           H  
HETATM   53  H20 UNL     1      -1.439   0.901   1.833  1.00  0.00           H  
HETATM   54  H21 UNL     1      -1.687   2.337   0.819  1.00  0.00           H  
HETATM   55  H22 UNL     1       0.503   2.564   0.234  1.00  0.00           H  
HETATM   56  H23 UNL     1       0.627   1.799   1.816  1.00  0.00           H  
HETATM   57  H24 UNL     1       0.887  -0.382   1.043  1.00  0.00           H  
HETATM   58  H25 UNL     1       3.871   2.245  -0.203  1.00  0.00           H  
HETATM   59  H26 UNL     1       3.322   1.425  -1.671  1.00  0.00           H  
HETATM   60  H27 UNL     1       2.244   2.544  -0.824  1.00  0.00           H  
HETATM   61  H28 UNL     1       2.640   2.120   1.774  1.00  0.00           H  
HETATM   62  H29 UNL     1       2.365   0.468   2.407  1.00  0.00           H  
HETATM   63  H30 UNL     1       4.979   1.765   1.438  1.00  0.00           H  
HETATM   64  H31 UNL     1       4.534   1.074   3.006  1.00  0.00           H  
HETATM   65  H32 UNL     1       4.458  -1.144   2.278  1.00  0.00           H  
HETATM   66  H33 UNL     1       6.647   0.478   1.772  1.00  0.00           H  
HETATM   67  H34 UNL     1       5.090  -0.184  -1.863  1.00  0.00           H  
HETATM   68  H35 UNL     1       5.772   0.807  -0.464  1.00  0.00           H  
HETATM   69  H36 UNL     1       6.423  -0.788  -0.867  1.00  0.00           H  
HETATM   70  H37 UNL     1       4.068  -2.884   0.679  1.00  0.00           H  
HETATM   71  H38 UNL     1       5.806  -2.498   0.702  1.00  0.00           H  
HETATM   72  H39 UNL     1       4.958  -2.730  -0.915  1.00  0.00           H  
HETATM   73  H40 UNL     1       2.588  -1.432   0.590  1.00  0.00           H  
HETATM   74  H41 UNL     1       3.136  -2.153  -1.644  1.00  0.00           H  
HETATM   75  H42 UNL     1       3.122  -0.506  -2.291  1.00  0.00           H  
HETATM   76  H43 UNL     1       1.001  -1.247  -2.720  1.00  0.00           H  
HETATM   77  H44 UNL     1       0.916  -2.247  -1.262  1.00  0.00           H  
HETATM   78  H45 UNL     1       0.077   1.954  -1.657  1.00  0.00           H  
HETATM   79  H46 UNL     1       1.190   0.975  -2.674  1.00  0.00           H  
HETATM   80  H47 UNL     1      -0.560   0.740  -2.763  1.00  0.00           H  
HETATM   81  H48 UNL     1      -3.103  -0.798   0.729  1.00  0.00           H  
CONECT    1    2    2   34   35
CONECT    2    3    4
CONECT    3   36   37   38
CONECT    4    5   33   39
CONECT    5    6   40   41
CONECT    6    7   42   43
CONECT    7    8   11   33
CONECT    8    9    9   10
CONECT   10   44
CONECT   11   12   45   46
CONECT   12   13   47   48
CONECT   13   14   15   31
CONECT   14   49   50   51
CONECT   15   16   33   52
CONECT   16   17   53   54
CONECT   17   18   55   56
CONECT   18   19   31   57
CONECT   19   20   21   28
CONECT   20   58   59   60
CONECT   21   22   61   62
CONECT   22   23   63   64
CONECT   23   24   25   65
CONECT   24   66
CONECT   25   26   27   28
CONECT   26   67   68   69
CONECT   27   70   71   72
CONECT   28   29   73
CONECT   29   30   74   75
CONECT   30   31   76   77
CONECT   31   32
CONECT   32   78   79   80
CONECT   33   81
END

HMDB0030094
     RDKit          3D
Betulinic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -3.8962    2.1376    2.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1699    1.0124    2.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5051   -0.1853    2.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1237    1.0477    0.5173 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4615    0.4428    0.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0998   -0.8728   -0.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547   -0.4405   -1.2522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9738    0.5878   -2.2700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6491    1.7714   -2.1688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109    0.2378   -3.4865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9714   -1.6084   -1.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5019   -1.4872   -1.7245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9141   -0.6859   -0.6217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8382   -1.5606    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7639    0.5604   -0.3107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1802    1.3249    0.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798    1.6124    0.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0356    0.4303    0.2677 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5349    0.6422    0.2252 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9736    1.7376   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9201    1.0314    1.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3919    0.9438    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8979   -0.4162    1.5556 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2883   -0.4622    1.7639 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693   -0.8581    0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4630   -0.1919   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727   -2.3653    0.1114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161   -0.7069   -0.1022 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7138   -1.1153   -1.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2372   -1.2231   -1.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589   -0.1137   -1.0067 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2472    0.9516   -2.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139    0.0718    0.0144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9271    2.1424    3.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6393    3.0657    2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9535   -0.1230    3.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2384   -1.1464    2.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5764   -0.2394    3.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9941    2.0586    0.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1234    0.1889    0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9877    1.1309   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8074   -1.1260   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8857   -1.6261    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5488    0.6528   -3.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3269   -1.8415   -2.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3198   -2.4992   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0852   -2.5354   -1.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694   -1.1947   -2.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9708   -1.0483    1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0847   -2.2023    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -2.3170    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7584    1.2072   -1.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4391    0.9010    1.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869    2.3366    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5033    2.5636    0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6271    1.7986    1.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871   -0.3824    1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8708    2.2452   -0.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215    1.4249   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2444    2.5443   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6401    2.1199    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3653    0.4680    2.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9791    1.7645    1.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5341    1.0744    3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4583   -1.1439    2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6468    0.4775    1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -0.1845   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7718    0.8070   -0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4230   -0.7880   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0679   -2.8838    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8062   -2.4980    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9585   -2.7303   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876   -1.4316    0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1357   -2.1529   -1.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1219   -0.5057   -2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0006   -1.2475   -2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9162   -2.2465   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0767    1.9542   -1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1897    0.9750   -2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604    0.7403   -2.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034   -0.7978    0.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 15 33  1  0
 33  4  1  0
 33  7  1  0
 31 13  1  0
 31 18  1  0
 28 19  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  1
  5 40  1  0
  5 41  1  0
  6 42  1  0
  6 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  6
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 18 57  1  1
 20 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  0
 22 64  1  0
 23 65  1  1
 24 66  1  0
 26 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 28 73  1  1
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 32 78  1  0
 32 79  1  0
 32 80  1  0
 33 81  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Mairin	ChEBI
Betulinate	Generator
3-Epi-betulinic acid	HMDB
Betulic acid	HMDB
(+)-Betulinic acid	PhytoBank
Betulinic acid	PhytoBank
Lupatic acid	PhytoBank
(3beta)-3-Hydroxylup-20(29)-en-28-oic acid	PhytoBank
(3β)-3-Hydroxylup-20(29)-en-28-oic acid	PhytoBank
3beta-Hydroxylup-20(29)-en-28-oic acid	PhytoBank
3β-Hydroxylup-20(29)-en-28-oic acid	PhytoBank
beta-Betulinic acid	PhytoBank
β-Betulinic acid	PhytoBank

Chemical Formula

C₃₀H₄₈O₃

Average Molecular Weight

456.711

Monoisotopic Molecular Weight

456.360345406

IUPAC Name

(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

Traditional Name

(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

CAS Registry Number

472-15-1

SMILES

[H][C@]12[C@@H](CC[C@@]1(CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O)C(C)=C

InChI Identifier

InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

InChI Key

QGJZLNKBHJESQX-FZFNOLFKSA-N

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
18-oxosteroid
18-hydroxysteroid
Oxosteroid
Hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:3087 )
pentacyclic triterpenoid (CHEBI:3087 )
Lupanes (C08619 )
Lupane triterpenoids (LMPR0106140004 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	316 - 318 °C	Not Available
Boiling Point	550.02 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0016 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	7.653 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0002 g/L	ALOGPS
logP	5.34	ALOGPS
logP	6.64	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.63 m³·mol⁻¹	ChemAxon
Polarizability	54.67 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	228.958	30932474
DeepCCS	[M+Na]+	202.849	30932474
AllCCS	[M+H]+	214.8	32859911
AllCCS	[M+H-H2O]+	213.1	32859911
AllCCS	[M+NH4]+	216.3	32859911
AllCCS	[M+Na]+	216.8	32859911
AllCCS	[M-H]-	212.3	32859911
AllCCS	[M+Na-2H]-	214.2	32859911
AllCCS	[M+HCOO]-	216.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.61 minutes	32390414
Predicted by Siyang on May 30, 2022	22.8928 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.57 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	54.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3374.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	547.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	280.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	203.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	721.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	935.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1063.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1738.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	662.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2049.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	652.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	600.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	231.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	531.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Betulinic acid	[H][C@]12[C@@H](CC[C@@]1(CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O)C(C)=C	3291.8	Standard polar	33892256
Betulinic acid	[H][C@]12[C@@H](CC[C@@]1(CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O)C(C)=C	3599.6	Standard non polar	33892256
Betulinic acid	[H][C@]12[C@@H](CC[C@@]1(CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O)C(C)=C	3671.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Betulinic acid,1TMS,isomer #1	C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12	3638.4	Semi standard non polar	33892256
Betulinic acid,1TMS,isomer #2	C=C(C)[C@@H]1CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12	3537.4	Semi standard non polar	33892256
Betulinic acid,2TMS,isomer #1	C=C(C)[C@@H]1CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12	3502.4	Semi standard non polar	33892256
Betulinic acid,1TBDMS,isomer #1	C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12	3857.7	Semi standard non polar	33892256
Betulinic acid,1TBDMS,isomer #2	C=C(C)[C@@H]1CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12	3799.8	Semi standard non polar	33892256
Betulinic acid,2TBDMS,isomer #1	C=C(C)[C@@H]1CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12	3999.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Betulinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOF	splash10-004i-0019400000-d634f687c0b20b3bf518	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOF	splash10-004i-0019400000-946b3acbf03ebc325984	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOF	splash10-06vi-0009700000-133d884e7fe1aabfb659	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOF	splash10-06vr-0019800000-a2c226a96551460f31b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOF	splash10-0a4i-0000411190-9e794d71d8e215a3ef7f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOF	splash10-0a4i-0000511290-00b42fd32f4bea1aac24	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-004i-0009100000-02c4ffe35137e2459ef9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-004i-0009100000-b369b92782bf0058f776	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-0udi-0000900000-31877b3328749253f478	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-0udi-0000900000-46226c91dca257ecbdbe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-004i-0119300000-d165dda7f84c911bb084	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-004i-0119400000-c8efa7eb386af139bbbb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-0udi-0000900000-5daf110b6535ef5e1cba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-0udi-0000900000-1a6ea554c157db014b7c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-01p9-0000900000-95cc62b5cf4bd28b6108	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOF	splash10-01p9-0000900000-1a328cc168bc37caf6d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid , positive-QTOF	splash10-0a4r-0920300000-e3035523b40f714793c7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-d90a9a8ffded459e1b38	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Betulinic acid 20V, Negative-QTOF	splash10-0a4i-0000900000-99c8bb2b318a1cfdacef	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betulinic acid 10V, Positive-QTOF	splash10-052r-0001900000-b8dd0421a0b0886464d3	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betulinic acid 20V, Positive-QTOF	splash10-01vy-0007900000-fa6391d5931c416add2d	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betulinic acid 40V, Positive-QTOF	splash10-0016-3359300000-9f556d5f0a61208b8cde	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betulinic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-5567c27847c37f89e74f	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betulinic acid 20V, Negative-QTOF	splash10-08fu-0003900000-4699eedd9cf8bfc1aa61	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Betulinic acid 40V, Negative-QTOF	splash10-000e-2007900000-4109b9ad459c3012d1ab	2017-06-28	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB12480

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Betulinic_acid

METLIN ID

Not Available

PubChem Compound

64971

PDB ID

Not Available

ChEBI ID

3087

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1223341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Rzeski W, Stepulak A, Szymanski M, Sifringer M, Kaczor J, Wejksza K, Zdzisinska B, Kandefer-Szerszen M: Betulinic acid decreases expression of bcl-2 and cyclin D1, inhibits proliferation, migration and induces apoptosis in cancer cells. Naunyn Schmiedebergs Arch Pharmacol. 2006 Oct;374(1):11-20. Epub 2006 Sep 9. [PubMed:16964520 ]
Lo YC, Chang YH, Wei BL, Huang YL, Chiou WF: Betulinic acid stimulates the differentiation and mineralization of osteoblastic MC3T3-E1 cells: involvement of BMP/Runx2 and beta-catenin signals. J Agric Food Chem. 2010 Jun 9;58(11):6643-9. doi: 10.1021/jf904158k. [PubMed:20443623 ]
Mukherjee R, Jaggi M, Rajendran P, Srivastava SK, Siddiqui MJ, Vardhan A, Burman AC: Synthesis of 3-O-acyl/3-benzylidene/3-hydrazone/3-hydrazine/17-carboxyacryloyl ester derivatives of betulinic acid as anti-angiogenic agents. Bioorg Med Chem Lett. 2004 Jun 21;14(12):3169-72. [PubMed:15149668 ]
Viji V, Shobha B, Kavitha SK, Ratheesh M, Kripa K, Helen A: Betulinic acid isolated from Bacopa monniera (L.) Wettst suppresses lipopolysaccharide stimulated interleukin-6 production through modulation of nuclear factor-kappaB in peripheral blood mononuclear cells. Int Immunopharmacol. 2010 Aug;10(8):843-9. doi: 10.1016/j.intimp.2010.04.013. Epub 2010 Apr 26. [PubMed:20430119 ]
Liu WK, Ho JC, Cheung FW, Liu BP, Ye WC, Che CT: Apoptotic activity of betulinic acid derivatives on murine melanoma B16 cell line. Eur J Pharmacol. 2004 Sep 13;498(1-3):71-8. [PubMed:15363977 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Betulinic acid (HMDB0030094)

MOL for HMDB0030094 (Betulinic acid)

3D MOL for HMDB0030094 (Betulinic acid)

3D SDF for HMDB0030094 (Betulinic acid)

3D-SDF for HMDB0030094 (Betulinic acid)

PDB for HMDB0030094 (Betulinic acid)

3D PDB for HMDB0030094 (Betulinic acid)

SMILES for HMDB0030094 (Betulinic acid)

INCHI for HMDB0030094 (Betulinic acid)

Structure for HMDB0030094 (Betulinic acid)

3D Structure for HMDB0030094 (Betulinic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra