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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:50 UTC

Update Date

2022-03-07 02:49:15 UTC

HMDB ID

HMDB0002364

Secondary Accession Numbers

HMDB02364

Metabolite Identification

Common Name

Oleanolic acid

Description

Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619 , 15522132 , 15994040 ).

Structure

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


  Mrv1652309272007302D          

 36 40  0  0  0  0            999 V2000
 9983.2622 9983.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.9732 9982.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1124 9983.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8254 9983.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1124 9982.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.9290 9986.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8677 9986.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.6863 9983.5317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8392 9983.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.7027 9981.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5509 9982.2875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8373 9982.6934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.5518 9981.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.2663 9981.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.1278 9983.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4133 9982.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.2629 9984.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5485 9983.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5485 9983.1125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9983.2629 9982.7001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9983.9725 9983.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.9725 9983.1134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9984.6870 9982.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.4014 9983.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.3987 9985.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.6843 9985.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.6843 9984.3573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9985.3987 9983.9449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9986.1132 9984.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1132 9985.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8380 9981.1568    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4134 9981.8681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9981.8389 9981.8681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9980.6107 9980.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.6512 9980.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.1260 9981.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 15 12  1  0  0  0  0
 12  9  1  1  0  0  0
 19 12  1  0  0  0  0
 19 11  1  6  0  0  0
 14 20  1  0  0  0  0
 20  1  1  1  0  0  0
 20 22  1  0  0  0  0
 22  2  1  6  0  0  0
 17 21  2  0  0  0  0
 25  6  1  0  0  0  0
 25  7  1  0  0  0  0
 27 21  1  0  0  0  0
 27  8  1  1  0  0  0
 24 28  1  0  0  0  0
 28  3  1  1  0  0  0
 33 31  1  6  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 13  1  0  0  0  0
 16 32  1  0  0  0  0
 32 10  1  1  0  0  0
M  END

HMDB0002364
     RDKit          3D
Oleanolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -3.8341   -2.0060   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6692   -1.2281   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7815   -2.0838    0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3666   -0.1068   -0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2676    0.7251   -1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5119    1.4547   -0.2919 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5436    2.3232    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8211    2.2953    1.5820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2691    3.2436   -0.4086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352    2.3447   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266    2.2911   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    0.9164   -0.2638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5106    0.2790   -1.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    0.0559    0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297   -1.0690    1.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553   -1.5924    0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540   -0.5687    0.3346 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6320   -0.7939    0.6799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9042   -0.4993    2.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0381   -2.2165    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -2.3839   -0.8417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716   -1.6426   -0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6816   -2.0634    0.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041   -0.1772   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1451    0.3704   -1.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7113    0.5696    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589    0.0682   -0.2918 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1070    1.5206   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    1.8819    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083    0.8420    0.4959 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3515    1.1559    1.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883    0.4913    0.7350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9811   -0.5504    1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382   -3.0162   -0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -1.5927   -1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4506   -2.2429   -1.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3854   -2.9435    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4606   -2.3794   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3793   -1.3951    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8944    0.5201   -0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0445   -0.4768   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7347    1.5390   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5979    0.1696   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0807    4.2485   -0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    3.4374   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    2.2375   -2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0472    2.9553    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305    2.8019   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -0.8028   -1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4575    0.5902   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749    0.6825   -2.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8339   -1.6771    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.0612    1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848   -2.4538    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -0.7508   -0.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    0.5360    2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462   -1.0668    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8697   -1.0085    2.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -2.9292    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6984   -2.5705    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0409   -3.4764   -0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -2.0428   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8569   -1.8865   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6694   -3.0429    0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969    1.4463   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -0.1426   -2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    0.1006   -2.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7248    0.0806    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4358    0.5422    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609    1.6052    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703   -0.1168   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6364    2.0817   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6644    1.7856    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5809    2.8372    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824    2.1670   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    1.9051    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1991    0.2905    2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6212    1.7328    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9184    1.1341    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8623    0.0100    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -1.2085    1.9056 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
  4  5  1  0
  5  6  1  0
  6  7  1  1
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  6
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  6
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  6
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  1
 33 80  1  0
 33 81  1  0
M  END


  Mrv1652309272007302D          

 36 40  0  0  0  0            999 V2000
 9983.2622 9983.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.9732 9982.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1124 9983.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.8254 9983.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1124 9982.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.9290 9986.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8677 9986.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.6863 9983.5317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8392 9983.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.7027 9981.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5509 9982.2875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8373 9982.6934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.5518 9981.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.2663 9981.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.1278 9983.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4133 9982.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.2629 9984.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5485 9983.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.5485 9983.1125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9983.2629 9982.7001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9983.9725 9983.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.9725 9983.1134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9984.6870 9982.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.4014 9983.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.3987 9985.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.6843 9985.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.6843 9984.3573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9985.3987 9983.9449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9986.1132 9984.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.1132 9985.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8380 9981.1568    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9980.4134 9981.8681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9981.8389 9981.8681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9980.6107 9980.8142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.6512 9980.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.1260 9981.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 15 12  1  0  0  0  0
 12  9  1  1  0  0  0
 19 12  1  0  0  0  0
 19 11  1  6  0  0  0
 14 20  1  0  0  0  0
 20  1  1  1  0  0  0
 20 22  1  0  0  0  0
 22  2  1  6  0  0  0
 17 21  2  0  0  0  0
 25  6  1  0  0  0  0
 25  7  1  0  0  0  0
 27 21  1  0  0  0  0
 27  8  1  1  0  0  0
 24 28  1  0  0  0  0
 28  3  1  1  0  0  0
 33 31  1  6  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 33  1  0  0  0  0
 12 33  1  0  0  0  0
 33 13  1  0  0  0  0
 16 32  1  0  0  0  0
 32 10  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0002364

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
MIJYXULNPSFWEK-GTOFXWBISA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.867786088496075

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
7.09

> <JCHEM_LOGP>
6.594833433333333

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433291560097

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744260336518661

> <JCHEM_PKA_STRONGEST_BASIC>
-0.835123022210091

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
133.62449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.17e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oleanolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002364
     RDKit          3D
Oleanolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -3.8341   -2.0060   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6692   -1.2281   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7815   -2.0838    0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3666   -0.1068   -0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2676    0.7251   -1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5119    1.4547   -0.2919 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5436    2.3232    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8211    2.2953    1.5820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2691    3.2436   -0.4086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352    2.3447   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266    2.2911   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    0.9164   -0.2638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5106    0.2790   -1.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    0.0559    0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297   -1.0690    1.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553   -1.5924    0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540   -0.5687    0.3346 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6320   -0.7939    0.6799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9042   -0.4993    2.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0381   -2.2165    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -2.3839   -0.8417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716   -1.6426   -0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6816   -2.0634    0.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041   -0.1772   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1451    0.3704   -1.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7113    0.5696    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589    0.0682   -0.2918 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1070    1.5206   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    1.8819    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083    0.8420    0.4959 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3515    1.1559    1.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883    0.4913    0.7350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9811   -0.5504    1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382   -3.0162   -0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -1.5927   -1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4506   -2.2429   -1.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3854   -2.9435    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4606   -2.3794   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3793   -1.3951    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8944    0.5201   -0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0445   -0.4768   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7347    1.5390   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5979    0.1696   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0807    4.2485   -0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    3.4374   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    2.2375   -2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0472    2.9553    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305    2.8019   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -0.8028   -1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4575    0.5902   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749    0.6825   -2.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8339   -1.6771    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.0612    1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848   -2.4538    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -0.7508   -0.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    0.5360    2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462   -1.0668    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8697   -1.0085    2.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -2.9292    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6984   -2.5705    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0409   -3.4764   -0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -2.0428   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8569   -1.8865   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6694   -3.0429    0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969    1.4463   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -0.1426   -2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    0.1006   -2.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7248    0.0806    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4358    0.5422    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609    1.6052    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703   -0.1168   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6364    2.0817   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6644    1.7856    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5809    2.8372    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824    2.1670   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    1.9051    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1991    0.2905    2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6212    1.7328    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9184    1.1341    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8623    0.0100    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -1.2085    1.9056 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
  4  5  1  0
  5  6  1  0
  6  7  1  1
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  6
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  6
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  6
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  1
 33 80  1  0
 33 81  1  0
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    8635.4238635.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8636.7508633.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8640.7438635.922   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8642.0748636.691   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8640.7438634.382   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8640.4018640.969   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8638.4208640.969   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0    8638.0818635.926   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8632.7668635.907   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8628.7788632.046   0.000  0.00  0.00           O+0
HETATM   11  H   UNK     0    8634.0958633.603   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    8632.7638634.361   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8634.0978632.051   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8635.4308632.821   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8631.4388635.131   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8630.1058634.361   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8635.4248637.453   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8634.0908636.683   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8634.0908635.143   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8635.4248634.374   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8636.7498636.685   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8636.7498635.145   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8638.0828634.375   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8639.4168635.145   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8639.4118639.777   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8638.0778639.007   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8638.0778637.467   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8639.4118636.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8640.7458637.467   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8640.7458639.007   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0    8632.7648631.493   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0    8630.1058632.820   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8632.7668632.820   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8630.4738630.853   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8632.4168630.872   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8631.4358632.053   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   22                                                            
CONECT    3    4    5   28                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6   25                                                            
CONECT    7   25                                                            
CONECT    8   27                                                            
CONECT    9   12                                                            
CONECT   10   32                                                            
CONECT   11   19                                                            
CONECT   12   15    9   19   33                                             
CONECT   13   14   33                                                       
CONECT   14   13   20                                                       
CONECT   15   16   12                                                       
CONECT   16   15   32                                                       
CONECT   17   18   21                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   12   11                                             
CONECT   20   19   14    1   22                                             
CONECT   21   22   17   27                                                  
CONECT   22   21   23   20    2                                             
CONECT   23   22   24                                                       
CONECT   24   23   28                                                       
CONECT   25   26   30    6    7                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   21    8                                             
CONECT   28   27   29   24    3                                             
CONECT   29   28   30                                                       
CONECT   30   25   29                                                       
CONECT   31   33                                                            
CONECT   32   36   16   10                                                  
CONECT   33   31   36   12   13                                             
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   34   35   32   33                                             
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0002364
HETATM    1  C1  UNL     1      -3.834  -2.006  -0.999  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.669  -1.228  -0.074  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.782  -2.084   0.509  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.367  -0.107  -0.847  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.268   0.725  -1.412  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.512   1.455  -0.292  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.544   2.323   0.361  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.821   2.295   1.582  1.00  0.00           O  
HETATM    9  O2  UNL     1      -5.269   3.244  -0.409  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.535   2.345  -0.942  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.127   2.291  -0.450  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.633   0.916  -0.264  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.511   0.279  -1.630  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.595   0.056   0.527  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.130  -1.069   1.024  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.255  -1.592   0.892  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.154  -0.569   0.335  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.632  -0.794   0.680  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.904  -0.499   2.117  1.00  0.00           C  
HETATM   20  C18 UNL     1       3.038  -2.216   0.425  1.00  0.00           C  
HETATM   21  C19 UNL     1       3.864  -2.384  -0.842  1.00  0.00           C  
HETATM   22  C20 UNL     1       5.172  -1.643  -0.554  1.00  0.00           C  
HETATM   23  O3  UNL     1       5.682  -2.063   0.648  1.00  0.00           O  
HETATM   24  C21 UNL     1       4.804  -0.177  -0.484  1.00  0.00           C  
HETATM   25  C22 UNL     1       5.145   0.370  -1.887  1.00  0.00           C  
HETATM   26  C23 UNL     1       5.711   0.570   0.455  1.00  0.00           C  
HETATM   27  C24 UNL     1       3.359   0.068  -0.292  1.00  0.00           C  
HETATM   28  C25 UNL     1       3.107   1.521  -0.002  1.00  0.00           C  
HETATM   29  C26 UNL     1       1.659   1.882   0.040  1.00  0.00           C  
HETATM   30  C27 UNL     1       0.708   0.842   0.496  1.00  0.00           C  
HETATM   31  C28 UNL     1       0.352   1.156   1.940  1.00  0.00           C  
HETATM   32  C29 UNL     1      -2.988   0.491   0.735  1.00  0.00           C  
HETATM   33  C30 UNL     1      -3.981  -0.550   1.077  1.00  0.00           C  
HETATM   34  H1  UNL     1      -3.638  -3.016  -0.533  1.00  0.00           H  
HETATM   35  H2  UNL     1      -2.859  -1.593  -1.243  1.00  0.00           H  
HETATM   36  H3  UNL     1      -4.451  -2.243  -1.904  1.00  0.00           H  
HETATM   37  H4  UNL     1      -5.385  -2.943   1.051  1.00  0.00           H  
HETATM   38  H5  UNL     1      -6.461  -2.379  -0.338  1.00  0.00           H  
HETATM   39  H6  UNL     1      -6.379  -1.395   1.161  1.00  0.00           H  
HETATM   40  H7  UNL     1      -5.894   0.520  -0.076  1.00  0.00           H  
HETATM   41  H8  UNL     1      -6.044  -0.477  -1.612  1.00  0.00           H  
HETATM   42  H9  UNL     1      -4.735   1.539  -2.015  1.00  0.00           H  
HETATM   43  H10 UNL     1      -3.598   0.170  -2.076  1.00  0.00           H  
HETATM   44  H11 UNL     1      -5.081   4.248  -0.358  1.00  0.00           H  
HETATM   45  H12 UNL     1      -2.832   3.437  -0.840  1.00  0.00           H  
HETATM   46  H13 UNL     1      -2.529   2.237  -2.070  1.00  0.00           H  
HETATM   47  H14 UNL     1      -1.047   2.955   0.430  1.00  0.00           H  
HETATM   48  H15 UNL     1      -0.531   2.802  -1.244  1.00  0.00           H  
HETATM   49  H16 UNL     1      -0.651  -0.803  -1.647  1.00  0.00           H  
HETATM   50  H17 UNL     1       0.457   0.590  -2.129  1.00  0.00           H  
HETATM   51  H18 UNL     1      -1.275   0.683  -2.341  1.00  0.00           H  
HETATM   52  H19 UNL     1      -1.834  -1.677   1.590  1.00  0.00           H  
HETATM   53  H20 UNL     1       0.613  -2.061   1.837  1.00  0.00           H  
HETATM   54  H21 UNL     1       0.185  -2.454   0.184  1.00  0.00           H  
HETATM   55  H22 UNL     1       1.168  -0.751  -0.790  1.00  0.00           H  
HETATM   56  H23 UNL     1       3.028   0.536   2.395  1.00  0.00           H  
HETATM   57  H24 UNL     1       2.146  -1.067   2.726  1.00  0.00           H  
HETATM   58  H25 UNL     1       3.870  -1.008   2.428  1.00  0.00           H  
HETATM   59  H26 UNL     1       2.200  -2.929   0.397  1.00  0.00           H  
HETATM   60  H27 UNL     1       3.698  -2.571   1.245  1.00  0.00           H  
HETATM   61  H28 UNL     1       4.041  -3.476  -0.947  1.00  0.00           H  
HETATM   62  H29 UNL     1       3.366  -2.043  -1.743  1.00  0.00           H  
HETATM   63  H30 UNL     1       5.857  -1.886  -1.366  1.00  0.00           H  
HETATM   64  H31 UNL     1       5.669  -3.043   0.768  1.00  0.00           H  
HETATM   65  H32 UNL     1       5.297   1.446  -1.814  1.00  0.00           H  
HETATM   66  H33 UNL     1       6.037  -0.143  -2.245  1.00  0.00           H  
HETATM   67  H34 UNL     1       4.280   0.101  -2.559  1.00  0.00           H  
HETATM   68  H35 UNL     1       6.725   0.081   0.366  1.00  0.00           H  
HETATM   69  H36 UNL     1       5.436   0.542   1.503  1.00  0.00           H  
HETATM   70  H37 UNL     1       5.861   1.605   0.061  1.00  0.00           H  
HETATM   71  H38 UNL     1       2.870  -0.117  -1.299  1.00  0.00           H  
HETATM   72  H39 UNL     1       3.636   2.082  -0.813  1.00  0.00           H  
HETATM   73  H40 UNL     1       3.664   1.786   0.920  1.00  0.00           H  
HETATM   74  H41 UNL     1       1.581   2.837   0.604  1.00  0.00           H  
HETATM   75  H42 UNL     1       1.382   2.167  -1.016  1.00  0.00           H  
HETATM   76  H43 UNL     1       1.074   1.905   2.385  1.00  0.00           H  
HETATM   77  H44 UNL     1       0.199   0.291   2.575  1.00  0.00           H  
HETATM   78  H45 UNL     1      -0.621   1.733   2.002  1.00  0.00           H  
HETATM   79  H46 UNL     1      -2.918   1.134   1.676  1.00  0.00           H  
HETATM   80  H47 UNL     1      -4.862   0.010   1.551  1.00  0.00           H  
HETATM   81  H48 UNL     1      -3.696  -1.209   1.906  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    4   33
CONECT    3   37   38   39
CONECT    4    5   40   41
CONECT    5    6   42   43
CONECT    6    7   10   32
CONECT    7    8    8    9
CONECT    9   44
CONECT   10   11   45   46
CONECT   11   12   47   48
CONECT   12   13   14   30
CONECT   13   49   50   51
CONECT   14   15   15   32
CONECT   15   16   52
CONECT   16   17   53   54
CONECT   17   18   30   55
CONECT   18   19   20   27
CONECT   19   56   57   58
CONECT   20   21   59   60
CONECT   21   22   61   62
CONECT   22   23   24   63
CONECT   23   64
CONECT   24   25   26   27
CONECT   25   65   66   67
CONECT   26   68   69   70
CONECT   27   28   71
CONECT   28   29   72   73
CONECT   29   30   74   75
CONECT   30   31
CONECT   31   76   77   78
CONECT   32   33   79
CONECT   33   80   81
END

HMDB0002364
     RDKit          3D
Oleanolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
   -3.8341   -2.0060   -0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6692   -1.2281   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7815   -2.0838    0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3666   -0.1068   -0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2676    0.7251   -1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5119    1.4547   -0.2919 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5436    2.3232    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8211    2.2953    1.5820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2691    3.2436   -0.4086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352    2.3447   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266    2.2911   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329    0.9164   -0.2638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5106    0.2790   -1.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    0.0559    0.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297   -1.0690    1.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553   -1.5924    0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540   -0.5687    0.3346 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6320   -0.7939    0.6799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9042   -0.4993    2.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0381   -2.2165    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8635   -2.3839   -0.8417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716   -1.6426   -0.5543 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6816   -2.0634    0.6482 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8041   -0.1772   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1451    0.3704   -1.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7113    0.5696    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589    0.0682   -0.2918 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1070    1.5206   -0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587    1.8819    0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7083    0.8420    0.4959 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3515    1.1559    1.9402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883    0.4913    0.7350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9811   -0.5504    1.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6382   -3.0162   -0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8592   -1.5927   -1.2427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4506   -2.2429   -1.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3854   -2.9435    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4606   -2.3794   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3793   -1.3951    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8944    0.5201   -0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0445   -0.4768   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7347    1.5390   -2.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5979    0.1696   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0807    4.2485   -0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8321    3.4374   -0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    2.2375   -2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0472    2.9553    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5305    2.8019   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514   -0.8028   -1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4575    0.5902   -2.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749    0.6825   -2.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8339   -1.6771    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129   -2.0612    1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848   -2.4538    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -0.7508   -0.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    0.5360    2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462   -1.0668    2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8697   -1.0085    2.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -2.9292    0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6984   -2.5705    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0409   -3.4764   -0.9465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3656   -2.0428   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8569   -1.8865   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6694   -3.0429    0.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2969    1.4463   -1.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0371   -0.1426   -2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    0.1006   -2.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7248    0.0806    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4358    0.5422    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609    1.6052    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703   -0.1168   -1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6364    2.0817   -0.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6644    1.7856    0.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5809    2.8372    0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3824    2.1670   -1.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0744    1.9051    2.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1991    0.2905    2.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6212    1.7328    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9184    1.1341    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8623    0.0100    1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6962   -1.2085    1.9056 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
  4  5  1  0
  5  6  1  0
  6  7  1  1
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
 14 32  1  0
 32 33  1  0
 33  2  1  0
 32  6  1  0
 30 12  1  0
 30 17  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 11 47  1  0
 11 48  1  0
 13 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  6
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 22 63  1  6
 23 64  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  6
 28 72  1  0
 28 73  1  0
 29 74  1  0
 29 75  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 32 79  1  1
 33 80  1  0
 33 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3beta-Hydroxyolean-12-en-28-Oic acid	ChEBI
Astrantiagenin C	ChEBI
Caryophyllin	ChEBI
Giganteumgenin C	ChEBI
Oleanic acid	ChEBI
Virgaureagenin b	ChEBI
Oleanolate	Kegg
3b-Hydroxyolean-12-en-28-Oate	Generator
3b-Hydroxyolean-12-en-28-Oic acid	Generator
3beta-Hydroxyolean-12-en-28-Oate	Generator
3Β-hydroxyolean-12-en-28-Oate	Generator
3Β-hydroxyolean-12-en-28-Oic acid	Generator
Oleanate	Generator
(3-beta)-3-Hydroxyolean-12-en-28-oate	HMDB
(3-beta)-3-Hydroxyolean-12-en-28-oic acid	HMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-oate	HMDB
(3.beta.)-3-beta-hydroxy-olean-12-en-28-oic acid	HMDB
(3.beta.)-3-hydroxy-olean-12-en-28-oate	HMDB
(3.beta.)-3-hydroxy-olean-12-en-28-oic acid	HMDB
(4AS,5S,6as,6BR,8R,8ar,10S,12ar,12BR,14BS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acid	HMDB
3-beta-Hydroxyolean-12-en-28-oate	HMDB
3-beta-Hydroxyolean-12-en-28-oic acid	HMDB
3.beta.-hydroxy-olean-12-en-28-oate	HMDB
3.beta.-hydroxy-olean-12-en-28-oic acid	HMDB
3beta-Hydroxy-olean-12-en-28-oate	HMDB
3beta-Hydroxy-olean-12-en-28-oic acid	HMDB
Oleanane triterpenes	MeSH, HMDB
Triterpenes, oleanane	MeSH, HMDB
Oleanol	MeSH, HMDB
Hederins	MeSH, HMDB
(3beta)-3-Hydroxyolean-12-en-28-oic acid	PhytoBank
(3β)-3-Hydroxyolean-12-en-28-oic acid	PhytoBank
(+)-Oleanolic acid	PhytoBank
Gledigenin 1	PhytoBank
Oleonolic acid	PhytoBank
OA	PhytoBank

Chemical Formula

C₃₀H₄₈O₃

Average Molecular Weight

456.711

Monoisotopic Molecular Weight

456.360345406

IUPAC Name

(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

oleanolic acid

CAS Registry Number

508-02-1

SMILES

[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

InChI Identifier

InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1

InChI Key

MIJYXULNPSFWEK-GTOFXWBISA-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
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:37659 )
pentacyclic triterpenoid (CHEBI:37659 )
Oleanane triterpenoids (C17148 )
Oleananes (C17148 )
Oleanane triterpenoids (LMPR0106150004 )

Ontology

Disposition

Biological location

Cellular substructure

Extracellular

Non-excretory biofluid

Blood

Excreta

Feces
Urine

Apple

Jujube
Fig

Quinoa

Oilseed crops

Sunflower

Vegetables

Fruit vegetables

Olive

Leaf vegetables

Lambsquarters

Shoot vegetables

American pokeweed

Onion-family vegetables

Garden onion

Cereals and cereal products

Cereals

Corn

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Gourds

Towel gourd

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	310 °C	Not Available
Boiling Point	553.00 to 554.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0017 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	8.576 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00082 g/L	ALOGPS
logP	7.09	ALOGPS
logP	6.59	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.74	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	1	ChemAxon
Refractivity	133.62 m³·mol⁻¹	ChemAxon
Polarizability	54.87 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
DarkChem	[M+H]+	205.708	31661259
DarkChem	[M-H]-	197.388	31661259
DeepCCS	[M-2H]-	232.012	30932474
DeepCCS	[M+Na]+	206.362	30932474
AllCCS	[M+H]+	216.7	32859911
AllCCS	[M+H-H2O]+	215.0	32859911
AllCCS	[M+NH4]+	218.2	32859911
AllCCS	[M+Na]+	218.6	32859911
AllCCS	[M-H]-	212.7	32859911
AllCCS	[M+Na-2H]-	214.7	32859911
AllCCS	[M+HCOO]-	217.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oleanolic acid	[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O	3223.1	Standard polar	33892256
Oleanolic acid	[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O	3628.5	Standard non polar	33892256
Oleanolic acid	[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O	3683.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oleanolic acid,1TMS,isomer #1	CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=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]2C1	3725.7	Semi standard non polar	33892256
Oleanolic acid,1TMS,isomer #2	CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1	3618.0	Semi standard non polar	33892256
Oleanolic acid,2TMS,isomer #1	CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)C(=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]2C1	3591.4	Semi standard non polar	33892256
Oleanolic acid,1TBDMS,isomer #1	CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=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]2C1	3953.4	Semi standard non polar	33892256
Oleanolic acid,1TBDMS,isomer #2	CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1	3887.1	Semi standard non polar	33892256
Oleanolic acid,2TBDMS,isomer #1	CC1(C)CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)C(=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]2C1	4090.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Oleanolic acid GC-MS (2 TMS)	splash10-0udi-2951000000-3ffcf6404c28c9072e6e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleanolic acid GC-MS (Non-derivatized)	splash10-0udi-2951000000-3ffcf6404c28c9072e6e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleanolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-0014900000-844b76f23b4a02a75c20	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleanolic acid GC-MS (2 TMS) - 70eV, Positive	splash10-000i-1011190000-4d07cbb48cd57a724a3c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleanolic 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 - Oleanolic acid LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOF	splash10-0a4i-0000900002-a0a4b7ccad94baf5df67	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleanolic acid 50V, Negative-QTOF	splash10-0a4i-0000900000-bc55e4c6ed84a38ec6a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOF	splash10-0a4i-0000900000-6a5c27def3e5639abbbc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleanolic acid 30V, Negative-QTOF	splash10-0a4i-0000900000-62f98aa71d39d7185d67	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-0492f069e415506430f0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOF	splash10-0a4i-0000900000-09b6dab9027bd312a816	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 10V, Positive-QTOF	splash10-052r-0001900000-948551e80a675e804945	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 20V, Positive-QTOF	splash10-01vx-0116900000-a7bbd734cfb389f003ce	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 40V, Positive-QTOF	splash10-001l-3459300000-fe5b4ff0a697d946a205	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-24b5f92b17a675bd0042	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOF	splash10-08fu-0003900000-df302b7b4b1f9bf77cc5	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOF	splash10-000e-2007900000-2e9882aa899cbe3bd6da	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-0d11296813b631a2140f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 20V, Negative-QTOF	splash10-0a4i-0000900000-a04074ef438068f127bb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 40V, Negative-QTOF	splash10-0a4i-0001900000-ec650846439f5cbbb4c2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 10V, Positive-QTOF	splash10-0a4i-0000900000-a2106bcf05d5c3dc7def	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 20V, Positive-QTOF	splash10-052r-0694700000-aa642e480c6b2dafc5d5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleanolic acid 40V, Positive-QTOF	splash10-00ei-0940000000-67c9b141383d1a95ec29	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.026 +/- 0.014 uM	Adult (>18 years old)	Male	Normal	16126358	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oleanolic_acid

METLIN ID

Not Available

PubChem Compound

10494

PDB ID

Not Available

ChEBI ID

37659

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1270801

References

Synthesis Reference

Corey, E. J.; Lee, Jaemoon. Enantioselective total synthesis of oleanolic acid, erythrodiol, b-amyrin, and other pentacyclic triterpenes from a common intermediate. Journal of the American Chemical Society (1993), 115(19), 8873-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Marquez-Martin A, De La Puerta R, Fernandez-Arche A, Ruiz-Gutierrez V, Yaqoob P: Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells. Cytokine. 2006 Dec;36(5-6):211-7. Epub 2007 Feb 9. [PubMed:17292619 ]
Rodriguez-Rodriguez R, Herrera MD, Perona JS, Ruiz-Gutierrez V: Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in 'orujo' olive oil, on rat aorta. Br J Nutr. 2004 Oct;92(4):635-42. [PubMed:15522132 ]
Liu J: Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol. 2005 Aug 22;100(1-2):92-4. [PubMed:15994040 ]

Showing metabocard for Oleanolic acid (HMDB0002364)

MOL for HMDB0002364 (Oleanolic acid)

3D MOL for HMDB0002364 (Oleanolic acid)

3D SDF for HMDB0002364 (Oleanolic acid)

3D-SDF for HMDB0002364 (Oleanolic acid)

PDB for HMDB0002364 (Oleanolic acid)

3D PDB for HMDB0002364 (Oleanolic acid)

SMILES for HMDB0002364 (Oleanolic acid)

INCHI for HMDB0002364 (Oleanolic acid)

Structure for HMDB0002364 (Oleanolic acid)

3D Structure for HMDB0002364 (Oleanolic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra