Details of the Drug

General Information of Drug (ID: DMWDMJ3)

Drug Name
OLEANOLIC_ACID
Synonyms
OLEANOLIC ACID; Oleanic acid; 508-02-1; Caryophyllin; Astrantiagenin C; Giganteumgenin C; Virgaureagenin B; 3beta-Hydroxyolean-12-en-28-oic acid; UNII-6SMK8R7TGJ; CCRIS 6493; (3-beta)-3-Hydroxyolean-12-en-28-oic acid; EINECS 208-081-6; NSC114945; 6SMK8R7TGJ; NSC-114945; 3-beta-Hydroxyolean-12-en-28-oic acid; CHEBI:37659; Olean-12-en-28-oic acid, 3-hydroxy-, (3beta)-; oleonolic acid; MFCD00064914
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 456.7
Logarithm of the Partition Coefficient (xlogp) 7.5
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C30H48O3
IUPAC Name
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Canonical SMILES
C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O
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
Cross-matching ID
PubChem CID
10494
ChEBI ID
CHEMBL168
CAS Number
508-02-1
TTD ID
D0SJ2Q
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Glycogen phosphorylase muscle form (GP) TTZHY6R PYGM_HUMAN Inhibitor [2]
Herpes simplex virus DNA polymerase UL30 (HSV UL30) TTIU7X1 DPOL_HHV11 Inhibitor [3]
PTPN1 messenger RNA (PTPN1 mRNA) TTELIN2 PTN1_HUMAN Inhibitor [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Autophagy protein 5 (ATG5) OT4T5SMS ATG5_HUMAN Gene/Protein Processing [5]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [6]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [6]
Forkhead box protein O3 (FOXO3) OTHXQG4P FOXO3_HUMAN Protein Interaction/Cellular Processes [7]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Gene/Protein Processing [8]
Microtubule-associated proteins 1A/1B light chain 3B (MAP1LC3B) OTUYHB84 MLP3B_HUMAN Gene/Protein Processing [9]
Mitochondrial import receptor subunit TOM20 homolog (TOMM20) OT76TPR2 TOM20_HUMAN Gene/Protein Processing [7]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 14 (MAPK14) OT5TCO3O MK14_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Glycogen phosphorylase muscle form (GP) DTT PYGM 2.69E-01 -0.23 -0.14
PTPN1 messenger RNA (PTPN1 mRNA) DTT PTPN1 9.44E-01 7.21E-03 0.08
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3306).
2 Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystal... J Med Chem. 2008 Jun 26;51(12):3540-54.
3 DNA polymerase beta inhibitors from Baeckea gunniana. J Nat Prod. 1999 Dec;62(12):1624-6.
4 Chemical Constituents of the Roots of Euphorbia micractina. J Nat Prod. 2009 Sep;72(9):1620-6.
5 SZC015, a synthetic oleanolic acid derivative, induces both apoptosis and autophagy in MCF-7 breast cancer cells. Chem Biol Interact. 2016 Jan 25;244:94-104. doi: 10.1016/j.cbi.2015.11.013. Epub 2015 Nov 21.
6 Oleanolic acid arrests cell cycle and induces apoptosis via ROS-mediated mitochondrial depolarization and lysosomal membrane permeabilization in human pancreatic cancer cells. J Appl Toxicol. 2013 Aug;33(8):756-65. doi: 10.1002/jat.2725. Epub 2012 Jun 8.
7 Oleanolic acid induces HCT116 colon cancer cell death through the p38/FOXO3a/Sirt6 pathway. Chem Biol Interact. 2022 Aug 25;363:110010. doi: 10.1016/j.cbi.2022.110010. Epub 2022 Jun 9.
8 [Apoptosis effects on human esophageal cancer cells by soyasaponin Bb and its machanism]. Wei Sheng Yan Jiu. 2010 Jul;39(4):444-6.
9 Oleanolic acid attenuates cisplatin-induced nephrotoxicity in mice and chemosensitizes human cervical cancer cells to cisplatin cytotoxicity. Food Chem Toxicol. 2019 Oct;132:110676. doi: 10.1016/j.fct.2019.110676. Epub 2019 Jul 12.