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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:51 UTC

Update Date

2022-03-07 02:49:15 UTC

HMDB ID

HMDB0002395

Secondary Accession Numbers

HMDB02395

Metabolite Identification

Common Name

Ursolic acid

Description

Ursolic 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. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040 , 17516235 , 17213663 ).

Structure

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


  Mrv1652309272007282D          

 36 40  0  0  0  0            999 V2000
 9983.4773 9983.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1883 9982.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3276 9983.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.0406 9984.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3276 9982.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9984.9014 9983.7469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0543 9983.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.9178 9981.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7660 9982.5026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0524 9982.9085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.7669 9981.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.4814 9982.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.3428 9983.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.6283 9982.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.4780 9984.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7636 9984.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7636 9983.3276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9983.4780 9982.9152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.1876 9984.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1876 9983.3285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9984.9021 9982.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6166 9983.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6139 9985.8100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.8994 9985.3975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.8994 9984.5725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9985.6139 9984.1601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9986.3284 9984.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3284 9985.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0531 9981.3719    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9980.6284 9982.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.0540 9982.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9980.8258 9981.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8663 9981.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.3410 9981.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1861 9985.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6139 9986.6337    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
 11 12  1  0  0  0  0
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 10 31  1  0  0  0  0
 31 11  1  0  0  0  0
 14 30  1  0  0  0  0
 30  8  1  1  0  0  0
 24 35  1  1  0  0  0
 23 36  1  6  0  0  0
M  END

HMDB0002395
     RDKit          3D
Ursolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
    2.9245   -2.5816    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5899   -1.2524    0.1330 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9798   -0.2253   -0.7742 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4979   -0.2032   -0.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592   -1.0079   -1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121   -1.1413   -1.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -0.3699   -0.6244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7679   -0.3186   -0.6877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1501    0.5188   -1.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -1.6822   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8340   -1.6024   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4704   -0.7539    0.1623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3816    0.1544   -0.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4493   -1.1218    2.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    1.0971    1.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1793    0.2049    0.6529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8371    1.6811    0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    1.9034    0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 78  1  6
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END


  Mrv1652309272007282D          

 36 40  0  0  0  0            999 V2000
 9983.4773 9983.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1883 9982.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3276 9983.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.0406 9984.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3276 9982.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9984.9014 9983.7469    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0543 9983.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.9178 9981.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7660 9982.5026    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0524 9982.9085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.7669 9981.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.4814 9982.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.3428 9983.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.6283 9982.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.4780 9984.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7636 9984.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7636 9983.3276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9983.4780 9982.9152    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.1876 9984.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1876 9983.3285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9984.9021 9982.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6166 9983.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6139 9985.8100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.8994 9985.3975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.8994 9984.5725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9985.6139 9984.1601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9986.3284 9984.5725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.3284 9985.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0531 9981.3719    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9980.6284 9982.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.0540 9982.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9980.8258 9981.0293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.8663 9981.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.3410 9981.6718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1861 9985.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6139 9986.6337    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
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 10  1  0  0  0  0
 10  7  1  1  0  0  0
 17 10  1  0  0  0  0
 17  9  1  6  0  0  0
 12 18  1  0  0  0  0
 18  1  1  1  0  0  0
 18 20  1  0  0  0  0
 20  2  1  6  0  0  0
 15 19  2  0  0  0  0
 25 19  1  0  0  0  0
 25  6  1  1  0  0  0
 22 26  1  0  0  0  0
 26  3  1  1  0  0  0
 31 29  1  6  0  0  0
 34 32  1  0  0  0  0
 34 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 11  1  0  0  0  0
 14 30  1  0  0  0  0
 30  8  1  1  0  0  0
 24 35  1  1  0  0  0
 23 36  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0002395

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12[C@@H](C)[C@H](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/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

> <INCHI_KEY>
WCGUUGGRBIKTOS-GPOJBZKASA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.50721270559766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,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>
6.35

> <JCHEM_LOGP>
6.581805409666667

> <ALOGPS_LOGS>
-5.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.489433291560097

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.744126566233528

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351230225624989

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
133.69799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.90e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ursolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002395
     RDKit          3D
Ursolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
    2.9245   -2.5816    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5899   -1.2524    0.1330 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9798   -0.2253   -0.7742 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4979   -0.2032   -0.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592   -1.0079   -1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121   -1.1413   -1.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -0.3699   -0.6244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7679   -0.3186   -0.6877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1501    0.5188   -1.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -1.6822   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8340   -1.6024   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4704   -0.7539    0.1623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3816    0.1544   -0.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5335   -0.1411    1.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4493   -1.1218    2.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    1.0971    1.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1793    0.2049    0.6529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8371    1.6811    0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    1.9034    0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    0.9803   -0.4095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3003    1.6562   -1.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.6826    0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6334   -0.0620    1.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446    1.9762    0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293    1.8365    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6224    1.1045   -0.4900 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6758    1.8972   -1.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1802    3.0374   -1.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2784    1.4044   -2.8743 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0612    0.9009   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128   -0.2294   -0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0154   -1.5072   -0.3722 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8493   -2.1632    0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0635   -3.0093    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -3.3241   -0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547   -2.6097   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7291   -0.8617    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -0.4990   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615   -1.6351   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554   -2.2332   -1.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9730   -0.9550   -2.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -0.9551    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190    1.5716   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727   -0.0157   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398    0.5816   -2.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941   -2.0919   -1.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0072   -2.4017   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652   -1.2265   -1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2096   -2.6697   -0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1784   -1.4465    0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5635    0.9372    0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -0.5693    3.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4172   -1.6359    2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6074   -1.8294    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1422    1.9749    1.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236    0.8189    2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    1.2441    2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535   -0.2095    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194    2.0607    1.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943    2.2708   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    2.9524    0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982    1.9997    1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    2.6917   -1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    1.0485   -2.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899    1.7540   -1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250    0.2078    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417    0.1771    2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -1.1603    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    2.7868   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    2.3638    1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547    2.8647    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1531    1.3611    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    1.8228   -3.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    0.7564    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6092    1.8659   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411   -0.0882   -1.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7894   -0.2640   -0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911   -2.2009   -1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8985   -2.1666    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -1.5254    1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5182   -3.2011    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 27 28  2  0
 27 29  1  0
 26 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32  2  1  0
 26  3  1  0
 22  4  1  0
 20  7  1  0
 17  8  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  3 38  1  6
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  1
 13 51  1  0
 15 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  1
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
 23 66  1  0
 23 67  1  0
 23 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  6
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8635.8248636.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8637.1528634.005   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8641.1458636.324   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8642.4768637.093   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8641.1458634.783   0.000  0.00  0.00           O+0
HETATM    6  H   UNK     0    8638.4838636.327   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8633.1688636.308   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8629.1808632.448   0.000  0.00  0.00           O+0
HETATM    9  H   UNK     0    8634.4968634.005   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8633.1648634.763   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8634.4988632.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8635.8328633.223   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8631.8408635.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8630.5068634.763   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8635.8268637.855   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8634.4928637.085   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8634.4928635.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8635.8268634.775   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8637.1508637.087   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8637.1508635.547   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8638.4848634.777   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8639.8188635.547   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8639.8138640.179   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8638.4798639.409   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8638.4798637.869   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8639.8138637.099   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8641.1468637.869   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8641.1468639.409   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0    8633.1668631.894   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0    8630.5068633.222   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8633.1678633.222   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8630.8758631.255   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8632.8178631.273   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8631.8378632.454   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8637.1478640.178   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8639.8138641.716   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   20                                                            
CONECT    3    4    5   26                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6   25                                                            
CONECT    7   10                                                            
CONECT    8   30                                                            
CONECT    9   17                                                            
CONECT   10   13    7   17   31                                             
CONECT   11   12   31                                                       
CONECT   12   11   18                                                       
CONECT   13   14   10                                                       
CONECT   14   13   30                                                       
CONECT   15   16   19                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   10    9                                             
CONECT   18   17   12    1   20                                             
CONECT   19   20   15   25                                                  
CONECT   20   19   21   18    2                                             
CONECT   21   20   22                                                       
CONECT   22   21   26                                                       
CONECT   23   24   28   36                                                  
CONECT   24   23   25   35                                                  
CONECT   25   24   26   19    6                                             
CONECT   26   25   27   22    3                                             
CONECT   27   26   28                                                       
CONECT   28   23   27                                                       
CONECT   29   31                                                            
CONECT   30   34   14    8                                                  
CONECT   31   29   34   10   11                                             
CONECT   32   34                                                            
CONECT   33   34                                                            
CONECT   34   32   33   30   31                                             
CONECT   35   24                                                            
CONECT   36   23                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0002395
HETATM    1  C1  UNL     1       2.925  -2.582   0.155  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.590  -1.252   0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.980  -0.225  -0.774  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.498  -0.203  -0.735  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.859  -1.008  -1.583  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.612  -1.141  -1.708  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.245  -0.370  -0.624  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.768  -0.319  -0.688  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.150   0.519  -1.847  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.347  -1.682  -0.846  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.834  -1.602  -0.899  1.00  0.00           C  
HETATM   12  C12 UNL     1      -5.470  -0.754   0.162  1.00  0.00           C  
HETATM   13  O1  UNL     1      -6.382   0.154  -0.422  1.00  0.00           O  
HETATM   14  C13 UNL     1      -4.533  -0.141   1.134  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.449  -1.122   2.329  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.192   1.097   1.765  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.179   0.205   0.653  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.837   1.681   0.640  1.00  0.00           C  
HETATM   19  C18 UNL     1      -1.380   1.903   0.452  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.616   0.980  -0.409  1.00  0.00           C  
HETATM   21  C20 UNL     1      -0.300   1.656  -1.752  1.00  0.00           C  
HETATM   22  C21 UNL     1       0.738   0.683   0.211  1.00  0.00           C  
HETATM   23  C22 UNL     1       0.633  -0.062   1.518  1.00  0.00           C  
HETATM   24  C23 UNL     1       1.445   1.976   0.465  1.00  0.00           C  
HETATM   25  C24 UNL     1       2.929   1.836   0.621  1.00  0.00           C  
HETATM   26  C25 UNL     1       3.622   1.105  -0.490  1.00  0.00           C  
HETATM   27  C26 UNL     1       3.676   1.897  -1.729  1.00  0.00           C  
HETATM   28  O2  UNL     1       3.180   3.037  -1.782  1.00  0.00           O  
HETATM   29  O3  UNL     1       4.278   1.404  -2.874  1.00  0.00           O  
HETATM   30  C27 UNL     1       5.061   0.901  -0.052  1.00  0.00           C  
HETATM   31  C28 UNL     1       5.713  -0.229  -0.771  1.00  0.00           C  
HETATM   32  C29 UNL     1       5.015  -1.507  -0.372  1.00  0.00           C  
HETATM   33  C30 UNL     1       5.849  -2.163   0.706  1.00  0.00           C  
HETATM   34  H1  UNL     1       3.063  -3.009   1.194  1.00  0.00           H  
HETATM   35  H2  UNL     1       3.446  -3.324  -0.498  1.00  0.00           H  
HETATM   36  H3  UNL     1       1.855  -2.610  -0.025  1.00  0.00           H  
HETATM   37  H4  UNL     1       3.729  -0.862   1.177  1.00  0.00           H  
HETATM   38  H5  UNL     1       3.346  -0.499  -1.812  1.00  0.00           H  
HETATM   39  H6  UNL     1       1.461  -1.635  -2.255  1.00  0.00           H  
HETATM   40  H7  UNL     1      -0.855  -2.233  -1.527  1.00  0.00           H  
HETATM   41  H8  UNL     1      -0.973  -0.955  -2.734  1.00  0.00           H  
HETATM   42  H9  UNL     1      -1.061  -0.955   0.329  1.00  0.00           H  
HETATM   43  H10 UNL     1      -2.819   1.572  -1.817  1.00  0.00           H  
HETATM   44  H11 UNL     1      -2.773  -0.016  -2.770  1.00  0.00           H  
HETATM   45  H12 UNL     1      -4.240   0.582  -2.046  1.00  0.00           H  
HETATM   46  H13 UNL     1      -2.994  -2.092  -1.816  1.00  0.00           H  
HETATM   47  H14 UNL     1      -3.007  -2.402  -0.073  1.00  0.00           H  
HETATM   48  H15 UNL     1      -5.165  -1.227  -1.912  1.00  0.00           H  
HETATM   49  H16 UNL     1      -5.210  -2.670  -0.896  1.00  0.00           H  
HETATM   50  H17 UNL     1      -6.178  -1.447   0.717  1.00  0.00           H  
HETATM   51  H18 UNL     1      -6.563   0.937   0.107  1.00  0.00           H  
HETATM   52  H19 UNL     1      -4.232  -0.569   3.263  1.00  0.00           H  
HETATM   53  H20 UNL     1      -5.417  -1.636   2.466  1.00  0.00           H  
HETATM   54  H21 UNL     1      -3.607  -1.829   2.178  1.00  0.00           H  
HETATM   55  H22 UNL     1      -5.142   1.975   1.126  1.00  0.00           H  
HETATM   56  H23 UNL     1      -6.224   0.819   2.104  1.00  0.00           H  
HETATM   57  H24 UNL     1      -4.637   1.244   2.739  1.00  0.00           H  
HETATM   58  H25 UNL     1      -2.453  -0.209   1.422  1.00  0.00           H  
HETATM   59  H26 UNL     1      -3.119   2.061   1.667  1.00  0.00           H  
HETATM   60  H27 UNL     1      -3.494   2.271  -0.037  1.00  0.00           H  
HETATM   61  H28 UNL     1      -1.273   2.952   0.037  1.00  0.00           H  
HETATM   62  H29 UNL     1      -0.898   2.000   1.471  1.00  0.00           H  
HETATM   63  H30 UNL     1      -0.700   2.692  -1.753  1.00  0.00           H  
HETATM   64  H31 UNL     1      -0.645   1.049  -2.613  1.00  0.00           H  
HETATM   65  H32 UNL     1       0.790   1.754  -1.935  1.00  0.00           H  
HETATM   66  H33 UNL     1      -0.225   0.208   2.141  1.00  0.00           H  
HETATM   67  H34 UNL     1       1.542   0.177   2.120  1.00  0.00           H  
HETATM   68  H35 UNL     1       0.627  -1.160   1.412  1.00  0.00           H  
HETATM   69  H36 UNL     1       1.227   2.787  -0.253  1.00  0.00           H  
HETATM   70  H37 UNL     1       1.086   2.364   1.461  1.00  0.00           H  
HETATM   71  H38 UNL     1       3.355   2.865   0.652  1.00  0.00           H  
HETATM   72  H39 UNL     1       3.153   1.361   1.574  1.00  0.00           H  
HETATM   73  H40 UNL     1       5.031   1.823  -3.368  1.00  0.00           H  
HETATM   74  H41 UNL     1       5.099   0.756   1.027  1.00  0.00           H  
HETATM   75  H42 UNL     1       5.609   1.866  -0.261  1.00  0.00           H  
HETATM   76  H43 UNL     1       5.741  -0.088  -1.867  1.00  0.00           H  
HETATM   77  H44 UNL     1       6.789  -0.264  -0.429  1.00  0.00           H  
HETATM   78  H45 UNL     1       4.991  -2.201  -1.250  1.00  0.00           H  
HETATM   79  H46 UNL     1       6.898  -2.167   0.333  1.00  0.00           H  
HETATM   80  H47 UNL     1       5.852  -1.525   1.624  1.00  0.00           H  
HETATM   81  H48 UNL     1       5.518  -3.201   0.916  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3   32   37
CONECT    3    4   26   38
CONECT    4    5    5   22
CONECT    5    6   39
CONECT    6    7   40   41
CONECT    7    8   20   42
CONECT    8    9   10   17
CONECT    9   43   44   45
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   14   50
CONECT   13   51
CONECT   14   15   16   17
CONECT   15   52   53   54
CONECT   16   55   56   57
CONECT   17   18   58
CONECT   18   19   59   60
CONECT   19   20   61   62
CONECT   20   21   22
CONECT   21   63   64   65
CONECT   22   23   24
CONECT   23   66   67   68
CONECT   24   25   69   70
CONECT   25   26   71   72
CONECT   26   27   30
CONECT   27   28   28   29
CONECT   29   73
CONECT   30   31   74   75
CONECT   31   32   76   77
CONECT   32   33   78
CONECT   33   79   80   81
END

HMDB0002395
     RDKit          3D
Ursolic acid
 81 85  0  0  0  0  0  0  0  0999 V2000
    2.9245   -2.5816    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5899   -1.2524    0.1330 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9798   -0.2253   -0.7742 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4979   -0.2032   -0.7350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592   -1.0079   -1.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6121   -1.1413   -1.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -0.3699   -0.6244 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7679   -0.3186   -0.6877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1501    0.5188   -1.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3470   -1.6822   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8340   -1.6024   -0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4704   -0.7539    0.1623 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3816    0.1544   -0.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5335   -0.1411    1.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4493   -1.1218    2.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    1.0971    1.7647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1793    0.2049    0.6529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8371    1.6811    0.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    1.9034    0.4520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164    0.9803   -0.4095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3003    1.6562   -1.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.6826    0.2114 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6334   -0.0620    1.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446    1.9762    0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293    1.8365    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6224    1.1045   -0.4900 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6758    1.8972   -1.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1802    3.0374   -1.7822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2784    1.4044   -2.8743 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0612    0.9009   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7128   -0.2294   -0.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0154   -1.5072   -0.3722 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8493   -2.1632    0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0635   -3.0093    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4458   -3.3241   -0.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547   -2.6097   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7291   -0.8617    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -0.4990   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615   -1.6351   -2.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8554   -2.2332   -1.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9730   -0.9550   -2.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0611   -0.9551    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8190    1.5716   -1.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727   -0.0157   -2.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2398    0.5816   -2.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941   -2.0919   -1.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0072   -2.4017   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1652   -1.2265   -1.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2096   -2.6697   -0.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1784   -1.4465    0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5635    0.9372    0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -0.5693    3.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4172   -1.6359    2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6074   -1.8294    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1422    1.9749    1.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236    0.8189    2.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    1.2441    2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535   -0.2095    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194    2.0607    1.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943    2.2708   -0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2730    2.9524    0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982    1.9997    1.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    2.6917   -1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6450    1.0485   -2.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899    1.7540   -1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2250    0.2078    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417    0.1771    2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -1.1603    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2272    2.7868   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    2.3638    1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547    2.8647    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1531    1.3611    1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0307    1.8228   -3.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    0.7564    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6092    1.8659   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7411   -0.0882   -1.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7894   -0.2640   -0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911   -2.2009   -1.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8985   -2.1666    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8525   -1.5254    1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5182   -3.2011    0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 27 28  2  0
 27 29  1  0
 26 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32  2  1  0
 26  3  1  0
 22  4  1  0
 20  7  1  0
 17  8  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  3 38  1  6
  5 39  1  0
  6 40  1  0
  6 41  1  0
  7 42  1  1
  9 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  1
 13 51  1  0
 15 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  1
 18 59  1  0
 18 60  1  0
 19 61  1  0
 19 62  1  0
 21 63  1  0
 21 64  1  0
 21 65  1  0
 23 66  1  0
 23 67  1  0
 23 68  1  0
 24 69  1  0
 24 70  1  0
 25 71  1  0
 25 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 31 76  1  0
 31 77  1  0
 32 78  1  6
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta)-3-Hydroxyurs-12-en-28-Oic acid	ChEBI
Malol	ChEBI
Prunol	ChEBI
Urson	ChEBI
(3b)-3-Hydroxyurs-12-en-28-Oate	Generator
(3b)-3-Hydroxyurs-12-en-28-Oic acid	Generator
(3beta)-3-Hydroxyurs-12-en-28-Oate	Generator
(3Β)-3-hydroxyurs-12-en-28-Oate	Generator
(3Β)-3-hydroxyurs-12-en-28-Oic acid	Generator
Ursolate	Generator
(3beta)-3-Hydroxy-urs-12-en-28-Oate	HMDB
(3beta)-3-Hydroxy-urs-12-en-28-Oic acid	HMDB
3beta-Hydroxy-12-ursen-28-ic acid	HMDB
3beta-Hydroxy-urs-12-en-28-Oate	HMDB
3beta-Hydroxy-urs-12-en-28-Oic acid	HMDB
3beta-Hydroxyurs-12-en-28-Oate	HMDB
3beta-Hydroxyurs-12-en-28-Oic acid	HMDB
3-Epi-ursolic acid	HMDB
Merotaine	HMDB
(+)-Ursolic acid	HMDB
3Β-hydroxyurs-12-en-28-Oic acid	HMDB
beta-Ursolic acid	HMDB
Β-ursolic acid	HMDB
Bungeolic acid	HMDB
Ursolisome	HMDB
UA	HMDB
Ursolic acid	HMDB

Chemical Formula

C₃₀H₄₈O₃

Average Molecular Weight

456.711

Monoisotopic Molecular Weight

456.360345406

IUPAC Name

(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,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

ursolic acid

CAS Registry Number

77-52-1

SMILES

[H][C@@]12[C@@H](C)[C@H](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/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

InChI Key

WCGUUGGRBIKTOS-GPOJBZKASA-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:9908 )
pentacyclic triterpenoid (CHEBI:9908 )
Taraxastane, ursane and bauerane triterpenoids (C08988 )
Ursanes (C08988 )
Taraxastane, ursane and bauerane triterpenoids (LMPR0106180007 )

Ontology

Not Available

Feces (PMID: 25037050)

Cellular substructure

Extracellular (HMDB: HMDB0002395)
Membrane (HMDB: HMDB0002395)

Source

Exogenous

Exogenous (HMDB: HMDB0002395)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Fruits (FooDB: FOOD00871)

Baking good

Condiment

Mustard (FooDB: FOOD00654)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Herb and spice

Herb

Endogenous

Endogenous (HMDB: HMDB0002395)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0002395)
Antioxidant (HMDB: HMDB0002395)

Antiviral agent (HMDB: HMDB0002395)
Central nervous system depressant (HMDB: HMDB0002395)
Hypoglycemic agent (HMDB: HMDB0002395)

Pharmaceutical industry

Antineoplastic agent

Hepatoprotective (HMDB: HMDB0002395)

Agriculture

Pesticide (HMDB: HMDB0002395)

Pesticide

Protisticide (HMDB: HMDB0002395)

Biological role

Modulator

Matrix metalloproteinase inhibitor (HMDB: HMDB0002395)
Anti Alzheimeran (HMDB: HMDB0002395)
Anti arrhythmic (HMDB: HMDB0002395)
Anti arthritic (HMDB: HMDB0002395)
Anti bacterial (HMDB: HMDB0002395)
Anti cancer (HMDB: HMDB0002395)
Anti carcinomic (HMDB: HMDB0002395)
Anti cariogenic (HMDB: HMDB0002395)
Anti cholestatic (HMDB: HMDB0002395)
Anti complement (HMDB: HMDB0002395)
Anti diabetic (HMDB: HMDB0002395)
Anti Epstein-Barr virus (HMDB: HMDB0002395)
Anti edemic (HMDB: HMDB0002395)
Anti escherichic (HMDB: HMDB0002395)
Anti fibrosarcomic (HMDB: HMDB0002395)
Anti hepatotoxic (HMDB: HMDB0002395)
Anti histaminic (HMDB: HMDB0002395)
Anti HIV (HMDB: HMDB0002395)
Anti hyperlipidemic (HMDB: HMDB0002395)
Anti-inflammatory (HMDB: HMDB0002395)
Anti leishmanic (HMDB: HMDB0002395)
Anti leukemic (HMDB: HMDB0002395)
Anti lymphomic (HMDB: HMDB0002395)
Anti malarial (HMDB: HMDB0002395)
Anti metastatic (HMDB: HMDB0002395)
Anti mutagenic (HMDB: HMDB0002395)
Anti nephritic (HMDB: HMDB0002395)
Anti obesity (HMDB: HMDB0002395)
Anti peroxidant (HMDB: HMDB0002395)
Anti plasmodial (HMDB: HMDB0002395)
Anti proliferative (HMDB: HMDB0002395)
Anti staphylococcic (HMDB: HMDB0002395)
Anti TGF-beta (HMDB: HMDB0002395)
Anti thromboxane (HMDB: HMDB0002395)
Anti trypanosomic (HMDB: HMDB0002395)
Anti ulcer (HMDB: HMDB0002395)
Candidicide (HMDB: HMDB0002395)
Cardioprotective (HMDB: HMDB0002395)
Cardiotonic (HMDB: HMDB0002395)
Choleretic (HMDB: HMDB0002395)
Cytotoxic (HMDB: HMDB0002395)
Hypotensive (HMDB: HMDB0002395)
Leucocytogenic (HMDB: HMDB0002395)
Piscicide (HMDB: HMDB0002395)
Potassium-sparing (HMDB: HMDB0002395)
Quinone-reductase inducer (HMDB: HMDB0002395)
Sodium-sparing (HMDB: HMDB0002395)
Trypanocide (HMDB: HMDB0002395)
Vasopressor (HMDB: HMDB0002395)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	182.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00059 g/L	ALOGPS
logP	6.35	ALOGPS
logP	6.58	ChemAxon
logS	-5.9	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	133.7 m³·mol⁻¹	ChemAxon
Polarizability	54.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	247.451	30932474
DeepCCS	[M+Na]+	221.314	30932474
AllCCS	[M+H]+	214.3	32859911
AllCCS	[M+H-H2O]+	212.6	32859911
AllCCS	[M+NH4]+	215.9	32859911
AllCCS	[M+Na]+	216.4	32859911
AllCCS	[M-H]-	210.5	32859911
AllCCS	[M+Na-2H]-	212.5	32859911
AllCCS	[M+HCOO]-	214.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.89 minutes	32390414
Predicted by Siyang on May 30, 2022	23.4012 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.56 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3405.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	580.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	281.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	209.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	683.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1016.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1079.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1800.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	676.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2047.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	711.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	597.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	245.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	589.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ursolic acid	[H][C@@]12[C@@H](C)[C@H](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	3401.4	Standard polar	33892256
Ursolic acid	[H][C@@]12[C@@H](C)[C@H](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	3658.3	Standard non polar	33892256
Ursolic acid	[H][C@@]12[C@@H](C)[C@H](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	3721.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ursolic acid,1TMS,isomer #1	C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O)CC[C@H]1C	3782.8	Semi standard non polar	33892256
Ursolic acid,1TMS,isomer #2	C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O[Si](C)(C)C)CC[C@H]1C	3678.0	Semi standard non polar	33892256
Ursolic acid,2TMS,isomer #1	C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O[Si](C)(C)C)CC[C@H]1C	3658.9	Semi standard non polar	33892256
Ursolic acid,1TBDMS,isomer #1	C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O)CC[C@H]1C	4006.6	Semi standard non polar	33892256
Ursolic acid,1TBDMS,isomer #2	C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@H]1C	3940.8	Semi standard non polar	33892256
Ursolic acid,2TBDMS,isomer #1	C[C@@H]1[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@H]1C	4143.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ursolic acid GC-MS (2 TMS)	splash10-0ue9-2941000000-2ca89e826b7fdd2c8c1c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ursolic acid GC-MS (Non-derivatized)	splash10-0ue9-2941000000-2ca89e826b7fdd2c8c1c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursolic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-0023900000-43b07991e5cfcd6c9419	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursolic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0079-1000190000-a9eb6c04f4325a25f377	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursolic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ursolic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid ESI-TOF , Negative-QTOF	splash10-0a4i-0000930000-25139768b4507e334b4a	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid ESI-TOF 30V, Negative-QTOF	splash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b8	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid ESI-TOF 20V, Negative-QTOF	splash10-0a4i-0000900000-63b4335e8110c54aba6e	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid ESI-TOF 50V, Negative-QTOF	splash10-0a4i-0000900000-b6287e2cceb1071deab7	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid ESI-TOF 10V, Negative-QTOF	splash10-0a4i-0000900000-27e80ae2f29ac7c2825c	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid ESI-TOF 40V, Negative-QTOF	splash10-0a4i-0000900000-433a030e07383bf9ecbf	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , negative-QTOF	splash10-0a4i-0000900000-315a19254ceeb5598e13	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , negative-QTOF	splash10-0a4i-0000900000-2eff827266b9664aa7cf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , negative-QTOF	splash10-0a4i-0000900000-ff12fe00efc56275c007	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , negative-QTOF	splash10-014l-0001223390-7f53534d3578e8cfc4b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOF	splash10-0a4i-0000900000-3ad5cc2bdb4d3808c5b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOF	splash10-0a4i-0000900000-63b4335e8110c54aba6e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOF	splash10-0a4i-0000900000-b6287e2cceb1071deab7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOF	splash10-0a4i-0000900000-27e80ae2f29ac7c2825c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid LC-ESI-TOF , negative-QTOF	splash10-0a4i-0000900000-433a030e07383bf9ecbf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , positive-QTOF	splash10-01t9-0029800000-86a594c11680cf4a317f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , positive-QTOF	splash10-0udi-0001211390-507a9b205eaa7310f0ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , positive-QTOF	splash10-004i-0037900000-08b9c68893f80ab994c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ursolic acid Linear Ion Trap , positive-QTOF	splash10-0w9u-0001223691-a434f7aa9337860104e7	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursolic acid 10V, Positive-QTOF	splash10-052r-0001900000-147d46bee2af34cb0e9e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursolic acid 20V, Positive-QTOF	splash10-01vx-1005900000-1032db86d8a91ecc2551	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursolic acid 40V, Positive-QTOF	splash10-055f-9468500000-8b9923090e53d44a56bf	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursolic acid 10V, Negative-QTOF	splash10-0a4i-0000900000-018366f20c7fedd5f9d2	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursolic acid 20V, Negative-QTOF	splash10-08fu-0003900000-ef66d040d6b775abb94e	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ursolic acid 40V, Negative-QTOF	splash10-0005-2008900000-0691b4da8771672d1def	2017-06-28	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	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

Associated Disorders and Diseases

Disease References

Colorectal cancer
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

BiGG ID

Not Available

Wikipedia Link

Ursolic acid

METLIN ID

Not Available

PubChem Compound

64945

PDB ID

Not Available

ChEBI ID

9908

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1410531

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Liu J: Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol. 2005 Aug 22;100(1-2):92-4. [PubMed:15994040 ]
Oh CJ, Kil IS, Park CI, Yang CH, Park JW: Ursolic acid regulates high glucose-induced apoptosis. Free Radic Res. 2007 Jun;41(6):638-44. [PubMed:17516235 ]
Achiwa Y, Hasegawa K, Udagawa Y: Regulation of the phosphatidylinositol 3-kinase-Akt and the mitogen-activated protein kinase pathways by ursolic acid in human endometrial cancer cells. Biosci Biotechnol Biochem. 2007 Jan;71(1):31-7. Epub 2007 Jan 7. [PubMed:17213663 ]

Showing metabocard for Ursolic acid (HMDB0002395)

MOL for HMDB0002395 (Ursolic acid)

3D MOL for HMDB0002395 (Ursolic acid)

3D SDF for HMDB0002395 (Ursolic acid)

3D-SDF for HMDB0002395 (Ursolic acid)

PDB for HMDB0002395 (Ursolic acid)

3D PDB for HMDB0002395 (Ursolic acid)

SMILES for HMDB0002395 (Ursolic acid)

INCHI for HMDB0002395 (Ursolic acid)

Structure for HMDB0002395 (Ursolic acid)

3D Structure for HMDB0002395 (Ursolic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra