Showing NP-Card for Oleanolic acid (NP0000372)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Show more...Show more...
Record Information
Version2.0
Created at2006-05-22 14:17:50 UTC
Updated at2024-09-17 15:41:46 UTC
NP-MRD IDNP0000372
Natural Product DOIhttps://doi.org/10.57994/1712
Secondary Accession NumbersNone
Natural Product Identification
Common NameOleanolic acid
DescriptionOleanolic 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000372 (Oleanolic acid)

  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
Download

3D MOL for NP0000372 (Oleanolic acid)

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
Download

3D SDF for NP0000372 (Oleanolic acid)

  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>
NP0000372

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000372 (Oleanolic acid)

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
Download

PDB for NP0000372 (Oleanolic acid)

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
Download

3D PDB for NP0000372 (Oleanolic acid)

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
Download

SMILES for NP0000372 (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
Download

INCHI for NP0000372 (Oleanolic acid)

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
Download
View in JSmolView NMR Assignments
Synonyms
Chemical FormulaC30H48O3
Average Mass456.7110 Da
Monoisotopic Mass456.36035 Da
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 Nameoleanolic acid
CAS Registry Number508-02-1
SMILES
CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1)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 KeyMIJYXULNPSFWEK-GTOFXWBISA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point310 °CNot Available
Boiling Point553.00 to 554.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0017 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP8.576 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.00082 g/LALOGPS
logP7.09ALOGPS
logP6.59ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.74ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.62 m³·mol⁻¹ChemAxon
Polarizability54.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002364
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013034
KNApSAcK IDC00019064
Chemspider ID10062
KEGG Compound IDC17148
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOleanolic_acid
METLIN IDNot Available
PubChem Compound10494
PDB IDNot Available
ChEBI ID37659
Good Scents IDrw1270801
References
General References
  1. 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 ]
  2. 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 ]
  3. Liu J: Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol. 2005 Aug 22;100(1-2):92-4. [PubMed:15994040 ]
  4. Kim JY, Lee KJ, Kim DH, Jeong TC, Lee ES, Choi YM, Jeong HG: Cytokine-mediated induction of metallothionein in Hepa-1c1c7 cells by oleanolic acid. Biochem Biophys Res Commun. 2004 Dec 17;325(3):792-7. doi: 10.1016/j.bbrc.2004.10.121. [PubMed:15541359 ]
  5. Chung S, Yoon HE, Kim SJ, Kim SJ, Koh ES, Hong YA, Park CW, Chang YS, Shin SJ: Oleanolic acid attenuates renal fibrosis in mice with unilateral ureteral obstruction via facilitating nuclear translocation of Nrf2. Nutr Metab (Lond). 2014 Jan 6;11(1):2. doi: 10.1186/1743-7075-11-2. [PubMed:24393202 ]