IMPPAT Phytochemical information: 
Ursolic acid
Ursolic acid
Summary

SMILES: C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C(=O)O
InChI: 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
InChIKey: WCGUUGGRBIKTOS-GPOJBZKASA-N
DeepSMILES: C[C@@H]CC[C@][C@@H][C@H]6C))C=CC[C@H][C@@][C@@]6CC%10))C))C)CC[C@@H][C@]6C)CC[C@@H]C6C)C))O))))))))))))))C=O)O
Scaffold Graph/Node/Bond level: C1=C2C3CCCCC3CCC2C2CCC3CCCCC3C2C1
Scaffold Graph/Node level: C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21
Scaffold Graph level: C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21
Functional groups: CC(=O)O; CC=C(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Triterpenoids
NP Classifier Class: Ursane and Taraxastane triterpenoids
Synonymous chemical names:
Ursolic acid, 3beta-hydroxy-12-ursen-28-oic acid, ursolic, ursolic-acid, ursolic acids, ursolic acid
External chemical identifiers:
CID:CID_64945; ChEMBL:CHEMBL169; ChEBI:CHEBI:9908; ZINC:ZINC000003978827; FDASRS:P3M2575F3F; SureChEMBL:SCHEMBL70205; MolPort-003-939-637
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ursolic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 456.71
Log P RDKit 7.09
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 27
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Ursolic acid
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.414109
Ursolic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Ursolic acid
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000505ENSG00000198793MTOR2475ChEMBL
TAR_EXP_001172ENSG00000178467P4HTM54681ChEMBL, NPASS
TAR_EXP_001178ENSG00000170242USP4755031BindingDB, ChEMBL, NPASS
TAR_EXP_001194ENSG00000132356PRKAA15562ChEMBL
TAR_EXP_001195ENSG00000162409PRKAA25563ChEMBL
TAR_EXP_001196ENSG00000111725PRKAB15564ChEMBL
TAR_EXP_001197ENSG00000131791PRKAB25565ChEMBL
TAR_EXP_001203ENSG00000181929PRKAG15571ChEMBL
TAR_EXP_000684ENSG00000116478HDAC13065ChEMBL
TAR_EXP_000504ENSG00000179593ALOX15B247BindingDB, ChEMBL, NPASS
TAR_EXP_000673ENSG00000111713GYS22998ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001222ENSG00000147099HDAC855869ChEMBL
TAR_EXP_001259ENSG00000129084PSMA15682ChEMBL
TAR_EXP_001260ENSG00000106588PSMA25683ChEMBL
TAR_EXP_001166ENSG00000186951PPARA5465ChEMBL, NPASS
TAR_EXP_001164ENSG00000135766EGLN154583BindingDB, ChEMBL, NPASS
TAR_EXP_000069ENSG00000087237CETP1071BindingDB, ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000707ENSG00000117594HSD11B13290BindingDB, ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000830ENSG00000105486LIG13978BindingDB, NPASS
TAR_EXP_000847ENSG00000101846STS412BindingDB, ChEMBL
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_001058ENSG00000106617PRKAG251422ChEMBL
TAR_EXP_001075ENSG00000061273HDAC751564ChEMBL
TAR_EXP_001098ENSG00000143727ACP152ChEMBL, NPASS
TAR_EXP_001150ENSG00000070501POLB5423BindingDB, ChEMBL, NPASS
TAR_EXP_000685ENSG00000196591HDAC23066ChEMBL
TAR_EXP_000124ENSG00000129521EGLN3112399ChEMBL, NPASS
TAR_EXP_000123ENSG00000269858EGLN2112398ChEMBL, NPASS
TAR_EXP_000102ENSG00000091428RAPGEF411069NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_001261ENSG00000100567PSMA35684ChEMBL
TAR_EXP_000065ENSG00000198848CES11066ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000005ENSG00000108840HDAC510014ChEMBL
TAR_EXP_001140ENSG00000115592PRKAG353632ChEMBL
TAR_EXP_001262ENSG00000041357PSMA45685ChEMBL
TAR_EXP_001267ENSG00000126067PSMB25690ChEMBL
TAR_EXP_001264ENSG00000100902PSMA65687ChEMBL
TAR_EXP_001360ENSG00000004700RECQL5965NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001378ENSG00000143365RORC6097BindingDB, ChEMBL, NPASS
TAR_EXP_001427ENSG00000177669MBOAT4619373ChEMBL, NPASS
TAR_EXP_001670ENSG00000196689TRPV17442ChEMBL, NPASS
TAR_EXP_001711ENSG00000187555USP77874BindingDB, ChEMBL, NPASS
TAR_EXP_001726ENSG00000163517HDAC1179885ChEMBL
TAR_EXP_001761ENSG00000100429HDAC1083933ChEMBL
TAR_EXP_001831ENSG00000171720HDAC38841ChEMBL
TAR_EXP_001926ENSG00000048052HDAC99734ChEMBL
TAR_EXP_001928ENSG00000068024HDAC49759ChEMBL
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_000667ENSG00000079387SENP129843BindingDB, ChEMBL
TAR_EXP_000660ENSG00000082701GSK3B2932ChEMBL, NPASS
TAR_EXP_000659ENSG00000105723GSK3A2931ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648NPASS
TAR_EXP_000519ENSG00000171298GAA2548BindingDB, ChEMBL, NPASS
TAR_EXP_000174ENSG00000222028PSMB11122706ChEMBL
TAR_EXP_000223ENSG00000154611PSMA8143471ChEMBL
TAR_EXP_000248ENSG00000117984CTSD1509BindingDB, ChEMBL, NPASS
TAR_EXP_000252ENSG00000179921GPBAR1151306BindingDB, ChEMBL, NPASS
TAR_EXP_000285ENSG00000137869CYP19A11588BindingDB, ChEMBL, NPASS
TAR_EXP_000357ENSG00000277571ELANE1991BindingDB
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000500ENSG00000275565ALOX5240BindingDB, ChEMBL, NPASS
TAR_EXP_001323ENSG00000142949PTPRF5792BindingDB, ChEMBL, NPASS
TAR_EXP_001263ENSG00000143106PSMA55686ChEMBL
TAR_EXP_000687ENSG00000100644HIF1A3091BindingDB, ChEMBL, NPASS
TAR_EXP_001322ENSG00000132334PTPRE5791ChEMBL, NPASS
TAR_EXP_001308ENSG00000175354PTPN25771BindingDB, ChEMBL, NPASS
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_001278ENSG00000205220PSMB105699ChEMBL
TAR_EXP_001311ENSG00000111679PTPN65777BindingDB, ChEMBL, NPASS
TAR_EXP_001276ENSG00000235715PSMB85696ChEMBL
TAR_EXP_001277ENSG00000239836PSMB95698ChEMBL
TAR_EXP_001274ENSG00000142507PSMB65694ChEMBL
TAR_EXP_001273ENSG00000100804PSMB55693ChEMBL
TAR_EXP_001270ENSG00000159377PSMB45692ChEMBL
TAR_EXP_001269ENSG00000277791PSMB35691ChEMBL
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_001266ENSG00000008018PSMB15689ChEMBL
TAR_EXP_001265ENSG00000101182PSMA75688ChEMBL
TAR_EXP_001275ENSG00000136930PSMB75695ChEMBL
TAR_EXP_001318ENSG00000132670PTPRA5786ChEMBL, NPASS