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
CHEBI:37659
CAS Number
508-02-1
TTD ID
D0SJ2Q
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
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [5]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [5]
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]
Beclin-1 (BECN1) OT4X293M BECN1_HUMAN Gene/Protein Processing [7]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [5]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [8]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [5]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [6]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [9]
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 Oleanolic acid and ursolic acid induce apoptosis in four human liver cancer cell lines. Toxicol In Vitro. 2010 Apr;24(3):842-8. doi: 10.1016/j.tiv.2009.12.008. Epub 2009 Dec 22.
9 Inhibition of cytochrome P450 activities by oleanolic acid and ursolic acid in human liver microsomes. Life Sci. 2004 Apr 16;74(22):2769-79.