IMPPAT Phytochemical information: 
Oleanolic acid
Oleanolic acid
Summary

SMILES: O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C
InChI: 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
InChIKey: MIJYXULNPSFWEK-GTOFXWBISA-N
DeepSMILES: O[C@H]CC[C@][C@H]C6C)C))CC[C@@][C@@H]6CC=C[C@@]6C)CC[C@@][C@H]6CCC)C)CC6)))))C=O)O))))))))))C)))))C
Scaffold Graph/Node/Bond level: C1=C2C3CCCCC3CCC2C2CCC3CCCCC3C2C1
Scaffold Graph/Node level: C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21
Scaffold Graph level: C1CCC2C(C1)CCC1C2CCC2C3CCCCC3CCC21
Functional groups: CO; CC=C(C)C; CC(=O)O
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: Oleanane triterpenoids
Synonymous chemical names:
oleanolic, oleanolic acid, oleanolic-acid, virgaureagenin b, Oleanolic acid, oleanolic acids, oleanic acid, Virgaureagenin B, 3beta-hydroxyolean-12-en-28-oic acid
External chemical identifiers:
CID:CID_10494; ChEMBL:CHEMBL168; ChEBI:CHEBI:37659; ZINC:ZINC000003785416; FDASRS:6SMK8R7TGJ; SureChEMBL:SCHEMBL71070; MolPort-004-955-261
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Oleanolic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 456.71
Log P RDKit 7.23
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 8
Stereochemical complexity RDKit 0.27
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
Oleanolic 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 0.409055
Oleanolic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.77
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
Oleanolic 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_000348ENSG00000146648EGFR1956BindingDB, ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000065ENSG00000198848CES11066ChEMBL, NPASS
TAR_EXP_000407ENSG00000117525F32152BindingDB, ChEMBL, NPASS
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000471ENSG00000124523SIRT523408ChEMBL
TAR_EXP_000500ENSG00000275565ALOX5240ChEMBL, NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247ChEMBL, NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932ChEMBL
TAR_EXP_000711ENSG00000086696HSD17B23294ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000752ENSG00000142192APP351ChEMBL, NPASS
TAR_EXP_000830ENSG00000105486LIG13978BindingDB, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000978ENSG00000007171NOS24843BindingDB, ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001036ENSG00000132646PCNA5111ChEMBL
TAR_EXP_001058ENSG00000106617PRKAG251422ChEMBL
TAR_EXP_001098ENSG00000143727ACP152ChEMBL, NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_001129ENSG00000170890PLA2G1B5319BindingDB, ChEMBL, NPASS
TAR_EXP_001139ENSG00000166851PLK15347NPASS
TAR_EXP_001140ENSG00000115592PRKAG353632ChEMBL
TAR_EXP_001150ENSG00000070501POLB5423BindingDB, ChEMBL, NPASS
TAR_EXP_000329ENSG00000108861DUSP31845BindingDB, ChEMBL, NPASS
TAR_EXP_000285ENSG00000137869CYP19A11588ChEMBL, NPASS
TAR_EXP_000252ENSG00000179921GPBAR1151306BindingDB, ChEMBL, NPASS
TAR_EXP_001164ENSG00000135766EGLN154583BindingDB, ChEMBL, NPASS
TAR_EXP_000140ENSG00000074416MGLL11343ChEMBL, NPASS
TAR_EXP_000124ENSG00000129521EGLN3112399ChEMBL, NPASS
TAR_EXP_000123ENSG00000269858EGLN2112398ChEMBL, NPASS
TAR_EXP_000102ENSG00000091428RAPGEF411069NPASS
TAR_EXP_000069ENSG00000087237CETP1071ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231NPASS
TAR_EXP_001308ENSG00000175354PTPN25771BindingDB, ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS
TAR_EXP_001942ENSG00000012504NR1H49971NPASS
TAR_EXP_001937ENSG00000101224CDC25B994ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001711ENSG00000187555USP77874BindingDB, ChEMBL
TAR_EXP_001670ENSG00000196689TRPV17442ChEMBL, NPASS
TAR_EXP_001667ENSG00000134086VHL7428ChEMBL
TAR_EXP_001619ENSG00000131747TOP2A7153ChEMBL, NPASS
TAR_EXP_001618ENSG00000198900TOP17150ChEMBL, NPASS
TAR_EXP_001568ENSG00000168610STAT36774ChEMBL, NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001311ENSG00000111679PTPN65777BindingDB, ChEMBL, NPASS
TAR_EXP_001316ENSG00000179295PTPN115781BindingDB, ChEMBL, NPASS
TAR_EXP_001318ENSG00000132670PTPRA5786ChEMBL, NPASS
TAR_EXP_001323ENSG00000142949PTPRF5792BindingDB, ChEMBL, NPASS
TAR_EXP_001322ENSG00000132334PTPRE5791ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_001320ENSG00000262418PTPRC5788BindingDB, ChEMBL, NPASS
TAR_EXP_001197ENSG00000131791PRKAB25565ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001203ENSG00000181929PRKAG15571ChEMBL
TAR_EXP_001196ENSG00000111725PRKAB15564ChEMBL
TAR_EXP_001195ENSG00000162409PRKAA25563ChEMBL
TAR_EXP_001194ENSG00000132356PRKAA15562ChEMBL
TAR_EXP_001172ENSG00000178467P4HTM54681ChEMBL, NPASS