Details of the Drug

General Information of Drug (ID: DM4SOAW)

Drug Name
URSOLIC ACID
Synonyms
Ursolic acid; Prunol; Malol; Urson; 77-52-1; 3beta-Hydroxyurs-12-en-28-oic acid; (3beta)-3-Hydroxyurs-12-en-28-oic acid; 3beta-Hydroxy-12-ursen-28-ic acid; UNII-P3M2575F3F; CHEBI:9908; CCRIS 7123; EINECS 201-034-0; CHEMBL169; Merotaine; AI3-03109; NSC4060; P3M2575F3F; NSC-4060; Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)-; HNMR; .beta.-Ursolic acid; NSC 4060; NSC 167406
Indication
Disease Entry ICD 11 Status REF
Metabolic syndrome x 5C50-5D2Z Phase 2 [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) 7.3
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C30H48O3
IUPAC Name
(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Canonical SMILES
C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)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
Cross-matching ID
PubChem CID
64945
ChEBI ID
CHEMBL169
CAS Number
77-52-1
UNII
P3M2575F3F
DrugBank ID
DB15588
TTD ID
D07LUJ
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
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) TTN7BL9 DHI1_HUMAN Inhibitor [2]
Glycogen phosphorylase muscle form (GP) TTZHY6R PYGM_HUMAN Inhibitor [3]
Herpes simplex virus DNA polymerase UL30 (HSV UL30) TTIU7X1 DPOL_HHV11 Inhibitor [4]
Phospholipase A2 (PLA2G1B) TT9V5JH PA21B_HUMAN Inhibitor [5]
PTPN1 messenger RNA (PTPN1 mRNA) TTELIN2 PTN1_HUMAN Inhibitor [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Acetyl-CoA carboxylase 1 (ACACA) OT5CQPZY ACACA_HUMAN Post-Translational Modifications [7]
Apoptosis-inducing factor 1, mitochondrial (AIFM1) OTKPWB7Q AIFM1_HUMAN Drug Response [8]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [9]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [8]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [7]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [7]
Cytochrome c (CYCS) OTBFALJD CYC_HUMAN Protein Interaction/Cellular Processes [10]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [11]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [7]
Eukaryotic translation initiation factor 2 subunit 1 (EIF2S1) OTM0GDTP IF2A_HUMAN Post-Translational Modifications [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Metabolic syndrome x
ICD Disease Classification 5C50-5D2Z
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
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) DTT HSD11B1 2.03E-01 -0.01 -0.08
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 ClinicalTrials.gov (NCT02337933) Effect of Ursolic Acid Administration on Insulin Sensitivity and Metabolic Syndrome. U.S. National Institutes of Health.
2 11beta-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational a... Bioorg Med Chem. 2010 Feb 15;18(4):1507-15.
3 Synthesis of 3-deoxypentacyclic triterpene derivatives as inhibitors of glycogen phosphorylase. J Nat Prod. 2009 Aug;72(8):1414-8.
4 DNA polymerase beta inhibitors from Baeckea gunniana. J Nat Prod. 1999 Dec;62(12):1624-6.
5 Synthesis of benzoyl phenyl benzoates as effective inhibitors for phospholipase A2 and hyaluronidase enzymes. Bioorg Med Chem Lett. 2005 Sep 15;15(18):4100-4.
6 Cytotoxic and PTP1B inhibitory activities from Erythrina abyssinica. Bioorg Med Chem Lett. 2009 Dec 1;19(23):6745-9.
7 Ursolic acid induces autophagy in U87MG cells via ROS-dependent endoplasmic reticulum stress. Chem Biol Interact. 2014 Jul 25;218:28-41. doi: 10.1016/j.cbi.2014.04.017. Epub 2014 May 5.
8 Ursolic acid induces doxorubicin-resistant HepG2 cell death via the release of apoptosis-inducing factor. Cancer Lett. 2010 Dec 1;298(1):128-38. doi: 10.1016/j.canlet.2010.06.010. Epub 2010 Jul 13.
9 Ursolic acid reduces Adriamycin resistance of human ovarian cancer cells through promoting the HuR translocation from cytoplasm to nucleus. Environ Toxicol. 2021 Feb;36(2):267-275. doi: 10.1002/tox.23032. Epub 2020 Oct 3.
10 Molecular mechanism of ursolic acid induced apoptosis in poorly differentiated endometrial cancer HEC108 cells. Oncol Rep. 2005 Aug;14(2):507-12.
11 Inhibition of cytochrome P450 activities by oleanolic acid and ursolic acid in human liver microsomes. Life Sci. 2004 Apr 16;74(22):2769-79.