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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:50 UTC

Update Date

2021-09-14 15:41:43 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 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


  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

$$$$

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC(C)(C)CC%5B...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:80})
 81 85  0  0  0  0  0  0  0  0999 V2000
   -3.3245    0.5499   -1.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9961    0.4705   -0.5299 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4050    1.7248    0.2316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9258    1.8708    0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2709    3.0893    1.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4894    2.0933   -1.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414    0.6251    0.9205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1404   -0.6308    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6219   -0.7768    0.0891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0379   -0.9988    1.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5439   -1.3110    1.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -0.2118    0.6851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6195    0.9492    1.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844    0.3272   -0.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695    0.6944   -1.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6110    0.5795   -1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3272    0.4066   -0.4962 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2178    1.3683    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8332    0.2266   -0.6958 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1357   -0.8708   -1.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3924    1.5501   -1.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109    1.4517   -1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5377    1.2459    0.0023 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3432    2.1296    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9555    1.0990   -0.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9780    0.0142    0.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -1.2505    0.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4039    0.1411    2.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4694   -0.0413    0.6621 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1018    0.7763    1.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8964   -1.3337    1.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169   -1.0655    1.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6441   -0.6867    0.3116 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4774   -1.9490   -0.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126   -1.9684   -0.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7656   -3.1861   -0.4506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576   -1.8247   -1.7934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0361    1.6824    1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9775    2.6049   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8278    3.9844    0.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3535    3.2063    1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8763    2.9417    2.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2368    1.2422   -1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5732    2.1953   -1.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0605    3.0011   -1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2079    0.5453    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6317    0.7209    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5561   -1.5080    0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5444   -0.6033   -0.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -0.1136    2.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5505   -1.8447    1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1638   -1.3764    2.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4038   -2.2919    0.9605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104    0.6341    2.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1598    1.8012    1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6017    1.2354    2.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4729    1.1123   -2.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8045   -0.2381   -2.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.5102   -2.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5636   -0.6925   -2.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2005   -0.8666   -1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -1.8384   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549    1.7401   -2.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293    2.3568   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2014    0.6565   -2.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2857    2.3978   -1.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3911    1.8626   -0.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6997   -1.2437    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -2.1277    0.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5216   -1.2820   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9899    1.0580    2.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0297   -0.7160    2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915    0.1705    2.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9824   -2.1622    0.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039   -1.5872    2.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9891   -1.9739    2.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952   -0.2775    2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626   -2.6622   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227   -1.6801   -1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4540   -2.3994   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5424   -3.9172   -1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
  5 42  1  0  0  0  0
  6 43  1  0  0  0  0
  6 44  1  0  0  0  0
  6 45  1  0  0  0  0
  7  8  1  0  0  0  0
  7 46  1  0  0  0  0
  7 47  1  0  0  0  0
  8  9  1  0  0  0  0
  8 48  1  0  0  0  0
  8 49  1  0  0  0  0
  9 10  1  0  0  0  0
  9 35  1  6  0  0  0
 10 11  1  0  0  0  0
 10 50  1  0  0  0  0
 10 51  1  0  0  0  0
 11 12  1  0  0  0  0
 11 52  1  0  0  0  0
 11 53  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 33  1  0  0  0  0
 13 54  1  0  0  0  0
 13 55  1  0  0  0  0
 13 56  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 57  1  0  0  0  0
 16 17  1  0  0  0  0
 16 58  1  0  0  0  0
 16 59  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 17 33  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 19 29  1  0  0  0  0
 20 60  1  0  0  0  0
 20 61  1  0  0  0  0
 20 62  1  0  0  0  0
 21 22  1  0  0  0  0
 21 63  1  0  0  0  0
 21 64  1  0  0  0  0
 22 23  1  0  0  0  0
 22 65  1  0  0  0  0
 22 66  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 25 67  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 68  1  0  0  0  0
 27 69  1  0  0  0  0
 27 70  1  0  0  0  0
 28 71  1  0  0  0  0
 28 72  1  0  0  0  0
 28 73  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 74  1  0  0  0  0
 31 75  1  0  0  0  0
 32 33  1  0  0  0  0
 32 76  1  0  0  0  0
 32 77  1  0  0  0  0
 33 34  1  6  0  0  0
 34 78  1  0  0  0  0
 34 79  1  0  0  0  0
 34 80  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 36 81  1  0  0  0  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    https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC(C)(C)CC%5B... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  H   UNL     1      -3.325   0.550  -1.576  1.00  0.00           H  
HETATM    2  C   UNL     1      -2.996   0.470  -0.530  1.00  0.00           C  
HETATM    3  C   UNL     1      -3.405   1.725   0.232  1.00  0.00           C  
HETATM    4  C   UNL     1      -4.926   1.871   0.286  1.00  0.00           C  
HETATM    5  C   UNL     1      -5.271   3.089   1.156  1.00  0.00           C  
HETATM    6  C   UNL     1      -5.489   2.093  -1.116  1.00  0.00           C  
HETATM    7  C   UNL     1      -5.541   0.625   0.920  1.00  0.00           C  
HETATM    8  C   UNL     1      -5.140  -0.631   0.157  1.00  0.00           C  
HETATM    9  C   UNL     1      -3.622  -0.777   0.089  1.00  0.00           C  
HETATM   10  C   UNL     1      -3.038  -0.999   1.480  1.00  0.00           C  
HETATM   11  C   UNL     1      -1.544  -1.311   1.396  1.00  0.00           C  
HETATM   12  C   UNL     1      -0.770  -0.212   0.685  1.00  0.00           C  
HETATM   13  C   UNL     1      -0.620   0.949   1.682  1.00  0.00           C  
HETATM   14  C   UNL     1      -1.484   0.327  -0.516  1.00  0.00           C  
HETATM   15  C   UNL     1      -0.870   0.694  -1.610  1.00  0.00           C  
HETATM   16  C   UNL     1       0.611   0.580  -1.834  1.00  0.00           C  
HETATM   17  C   UNL     1       1.327   0.407  -0.496  1.00  0.00           C  
HETATM   18  H   UNL     1       1.218   1.368   0.049  1.00  0.00           H  
HETATM   19  C   UNL     1       2.833   0.227  -0.696  1.00  0.00           C  
HETATM   20  C   UNL     1       3.136  -0.871  -1.709  1.00  0.00           C  
HETATM   21  C   UNL     1       3.392   1.550  -1.247  1.00  0.00           C  
HETATM   22  C   UNL     1       4.911   1.452  -1.371  1.00  0.00           C  
HETATM   23  C   UNL     1       5.538   1.246   0.002  1.00  0.00           C  
HETATM   24  H   UNL     1       5.343   2.130   0.621  1.00  0.00           H  
HETATM   25  O   UNL     1       6.955   1.099  -0.142  1.00  0.00           O  
HETATM   26  C   UNL     1       4.978   0.014   0.714  1.00  0.00           C  
HETATM   27  C   UNL     1       5.639  -1.250   0.167  1.00  0.00           C  
HETATM   28  C   UNL     1       5.404   0.141   2.199  1.00  0.00           C  
HETATM   29  C   UNL     1       3.469  -0.041   0.662  1.00  0.00           C  
HETATM   30  H   UNL     1       3.102   0.776   1.333  1.00  0.00           H  
HETATM   31  C   UNL     1       2.896  -1.334   1.243  1.00  0.00           C  
HETATM   32  C   UNL     1       1.417  -1.065   1.567  1.00  0.00           C  
HETATM   33  C   UNL     1       0.644  -0.687   0.312  1.00  0.00           C  
HETATM   34  C   UNL     1       0.477  -1.949  -0.551  1.00  0.00           C  
HETATM   35  C   UNL     1      -3.313  -1.968  -0.788  1.00  0.00           C  
HETATM   36  O   UNL     1      -3.766  -3.186  -0.451  1.00  0.00           O  
HETATM   37  O   UNL     1      -2.658  -1.825  -1.793  1.00  0.00           O  
HETATM   38  H   UNL     1      -3.036   1.682   1.258  1.00  0.00           H  
HETATM   39  H   UNL     1      -2.978   2.605  -0.257  1.00  0.00           H  
HETATM   40  H   UNL     1      -4.828   3.984   0.719  1.00  0.00           H  
HETATM   41  H   UNL     1      -6.354   3.206   1.204  1.00  0.00           H  
HETATM   42  H   UNL     1      -4.876   2.942   2.161  1.00  0.00           H  
HETATM   43  H   UNL     1      -5.237   1.242  -1.748  1.00  0.00           H  
HETATM   44  H   UNL     1      -6.573   2.195  -1.060  1.00  0.00           H  
HETATM   45  H   UNL     1      -5.061   3.001  -1.540  1.00  0.00           H  
HETATM   46  H   UNL     1      -5.208   0.545   1.958  1.00  0.00           H  
HETATM   47  H   UNL     1      -6.632   0.721   0.915  1.00  0.00           H  
HETATM   48  H   UNL     1      -5.556  -1.508   0.663  1.00  0.00           H  
HETATM   49  H   UNL     1      -5.544  -0.603  -0.856  1.00  0.00           H  
HETATM   50  H   UNL     1      -3.198  -0.114   2.096  1.00  0.00           H  
HETATM   51  H   UNL     1      -3.550  -1.845   1.951  1.00  0.00           H  
HETATM   52  H   UNL     1      -1.164  -1.376   2.434  1.00  0.00           H  
HETATM   53  H   UNL     1      -1.404  -2.292   0.961  1.00  0.00           H  
HETATM   54  H   UNL     1       0.010   0.634   2.514  1.00  0.00           H  
HETATM   55  H   UNL     1      -0.160   1.801   1.181  1.00  0.00           H  
HETATM   56  H   UNL     1      -1.602   1.235   2.058  1.00  0.00           H  
HETATM   57  H   UNL     1      -1.473   1.112  -2.404  1.00  0.00           H  
HETATM   58  H   UNL     1       0.804  -0.238  -2.519  1.00  0.00           H  
HETATM   59  H   UNL     1       0.958   1.510  -2.305  1.00  0.00           H  
HETATM   60  H   UNL     1       2.564  -0.693  -2.620  1.00  0.00           H  
HETATM   61  H   UNL     1       4.200  -0.867  -1.942  1.00  0.00           H  
HETATM   62  H   UNL     1       2.859  -1.838  -1.290  1.00  0.00           H  
HETATM   63  H   UNL     1       2.955   1.740  -2.226  1.00  0.00           H  
HETATM   64  H   UNL     1       3.129   2.357  -0.564  1.00  0.00           H  
HETATM   65  H   UNL     1       5.201   0.656  -2.049  1.00  0.00           H  
HETATM   66  H   UNL     1       5.286   2.398  -1.789  1.00  0.00           H  
HETATM   67  H   UNL     1       7.391   1.863  -0.544  1.00  0.00           H  
HETATM   68  H   UNL     1       6.700  -1.244   0.417  1.00  0.00           H  
HETATM   69  H   UNL     1       5.167  -2.128   0.609  1.00  0.00           H  
HETATM   70  H   UNL     1       5.522  -1.282  -0.917  1.00  0.00           H  
HETATM   71  H   UNL     1       4.990   1.058   2.618  1.00  0.00           H  
HETATM   72  H   UNL     1       5.030  -0.716   2.758  1.00  0.00           H  
HETATM   73  H   UNL     1       6.492   0.171   2.263  1.00  0.00           H  
HETATM   74  H   UNL     1       2.982  -2.162   0.555  1.00  0.00           H  
HETATM   75  H   UNL     1       3.404  -1.587   2.175  1.00  0.00           H  
HETATM   76  H   UNL     1       0.989  -1.974   2.000  1.00  0.00           H  
HETATM   77  H   UNL     1       1.395  -0.278   2.317  1.00  0.00           H  
HETATM   78  H   UNL     1      -0.163  -2.662  -0.032  1.00  0.00           H  
HETATM   79  H   UNL     1       0.023  -1.680  -1.505  1.00  0.00           H  
HETATM   80  H   UNL     1       1.454  -2.399  -0.729  1.00  0.00           H  
HETATM   81  H   UNL     1      -3.542  -3.917  -1.043  1.00  0.00           H  
CONECT    1    2                                                      
CONECT    2    1    3    9   14                                       
CONECT    3    2    4   38   39                                       
CONECT    4    3    5    6    7                                       
CONECT    5    4   40   41   42                                       
CONECT    6    4   43   44   45                                       
CONECT    7    4    8   46   47                                       
CONECT    8    7    9   48   49                                       
CONECT    9    8    2   10   35                                       
CONECT   10    9   11   50   51                                       
CONECT   11   10   12   52   53                                       
CONECT   12   11   13   14   33                                       
CONECT   13   12   54   55   56                                       
CONECT   14   12    2   15   15                                       
CONECT   15   14   14   16   57                                       
CONECT   16   15   17   58   59                                       
CONECT   17   16   18   19   33                                       
CONECT   18   17                                                      
CONECT   19   17   20   21   29                                       
CONECT   20   19   60   61   62                                       
CONECT   21   19   22   63   64                                       
CONECT   22   21   23   65   66                                       
CONECT   23   22   24   25   26                                       
CONECT   24   23                                                      
CONECT   25   23   67                                                 
CONECT   26   23   27   28   29                                       
CONECT   27   26   68   69   70                                       
CONECT   28   26   71   72   73                                       
CONECT   29   26   19   30   31                                       
CONECT   30   29                                                      
CONECT   31   29   32   74   75                                       
CONECT   32   31   33   76   77                                       
CONECT   33   32   12   17   34                                       
CONECT   34   33   78   79   80                                       
CONECT   35    9   36   37   37                                       
CONECT   36   35   81                                                 
CONECT   37   35   35                                                 
CONECT   38    3                                                      
CONECT   39    3                                                      
CONECT   40    5                                                      
CONECT   41    5                                                      
CONECT   42    5                                                      
CONECT   43    6                                                      
CONECT   44    6                                                      
CONECT   45    6                                                      
CONECT   46    7                                                      
CONECT   47    7                                                      
CONECT   48    8                                                      
CONECT   49    8                                                      
CONECT   50   10                                                      
CONECT   51   10                                                      
CONECT   52   11                                                      
CONECT   53   11                                                      
CONECT   54   13                                                      
CONECT   55   13                                                      
CONECT   56   13                                                      
CONECT   57   15                                                      
CONECT   58   16                                                      
CONECT   59   16                                                      
CONECT   60   20                                                      
CONECT   61   20                                                      
CONECT   62   20                                                      
CONECT   63   21                                                      
CONECT   64   21                                                      
CONECT   65   22                                                      
CONECT   66   22                                                      
CONECT   67   25                                                      
CONECT   68   27                                                      
CONECT   69   27                                                      
CONECT   70   27                                                      
CONECT   71   28                                                      
CONECT   72   28                                                      
CONECT   73   28                                                      
CONECT   74   31                                                      
CONECT   75   31                                                      
CONECT   76   32                                                      
CONECT   77   32                                                      
CONECT   78   34                                                      
CONECT   79   34                                                      
CONECT   80   34                                                      
CONECT   81   36                                                      
MASTER        0    0    0    0    0    0    0    0   81    0   81    0
END

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC(C)(C)CC%5B...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:80})
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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	HMDB
Triterpenes, oleanane	HMDB
Oleanol	HMDB
Hederins	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

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	310 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted 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

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-2951000000-3ffcf6404c28c9072e6e	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-2951000000-3ffcf6404c28c9072e6e	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-0014900000-844b76f23b4a02a75c20	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-000i-1011190000-4d07cbb48cd57a724a3c	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-0023900000-56b699a28dcac02b8121	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative	splash10-0a4i-0000900002-a0a4b7ccad94baf5df67	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0001900000-948551e80a675e804945	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01vx-0116900000-a7bbd734cfb389f003ce	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001l-3459300000-fe5b4ff0a697d946a205	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-24b5f92b17a675bd0042	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fu-0003900000-df302b7b4b1f9bf77cc5	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000e-2007900000-2e9882aa899cbe3bd6da	2017-06-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-0d11296813b631a2140f	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000900000-a04074ef438068f127bb	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0001900000-ec650846439f5cbbb4c2	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000900000-a2106bcf05d5c3dc7def	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0694700000-aa642e480c6b2dafc5d5	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ei-0940000000-67c9b141383d1a95ec29	2021-09-07	View Spectrum

NMR

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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	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

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)

GC-MS

LC-MS/MS

NMR