Details of the Drug

General Information of Drug (ID: DMBUI2A)

Drug Name
BETULINIC ACID
Synonyms
betulinic acid; 472-15-1; Mairin; Betulic acid; NSC 113090; CCRIS 6748; 3-Hydroxylup-20(29)-en-28-oic acid; UNII-4G6A18707N; 3beta-Hydroxy-20(29)-lupaene-28-oic acid; EINECS 207-448-8; NSC677578; als-357; NSC 677578; CHEMBL269277; CHEBI:3087; 3beta-Hydroxy-lup-20(29)-en-28-oic acid; 4G6A18707N; Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-; AK-72848; Lupatic Acid; SMR000445624
Indication
Disease Entry ICD 11 Status REF
Melanoma 2C30 Phase 1 [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) 8.2
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C30H48O3
IUPAC Name
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Canonical SMILES
CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=O)O
InChI
InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
InChIKey
QGJZLNKBHJESQX-FZFNOLFKSA-N
Cross-matching ID
PubChem CID
64971
ChEBI ID
CHEMBL269277
CAS Number
472-15-1
UNII
4G6A18707N
DrugBank ID
DB12480
TTD ID
D0R9YR
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

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Herpes simplex virus DNA polymerase UL30 (HSV UL30) TTIU7X1 DPOL_HHV11 Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [3]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [4]
Carbonic anhydrase 9 (CA9) OTNA51XT CAH9_HUMAN Gene/Protein Processing [5]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Gene/Protein Processing [6]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [7]
Microtubule-associated proteins 1A/1B light chain 3B (MAP1LC3B) OTUYHB84 MLP3B_HUMAN Gene/Protein Processing [6]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [8]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [8]
Parathyroid hormone-related protein (PTHLH) OTI1JF13 PTHR_HUMAN Gene/Protein Processing [9]
Phospholipase A2, membrane associated (PLA2G2A) OT1NY7BF PA2GA_HUMAN Protein Interaction/Cellular Processes [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction 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: 3945).
2 DNA polymerase beta inhibitors from Tetracera boiviniana. J Nat Prod. 1999 Dec;62(12):1660-3.
3 Betulinyl Sulfamates as Anticancer Agents and Radiosensitizers in Human Breast Cancer Cells. Int J Mol Sci. 2015 Nov 3;16(11):26249-62. doi: 10.3390/ijms161125953.
4 Hypoxia increases the apoptotic response to betulinic acid and betulin in human non-small cell lung cancer cells. Chem Biol Interact. 2021 Jan 5;333:109320. doi: 10.1016/j.cbi.2020.109320. Epub 2020 Nov 9.
5 Synthesis and biological investigation of new carbonic anhydrase IX (CAIX) inhibitors. Chem Biol Interact. 2018 Mar 25;284:12-23. doi: 10.1016/j.cbi.2018.02.014. Epub 2018 Feb 16.
6 Effects and mechanisms of betulinic acid on improving EGFR TKI-resistance of lung cancer cells. Environ Toxicol. 2018 Nov;33(11):1153-1159.
7 Biological evaluation of a halogenated triterpenoid, 2-bromo-dihydrobelulonic acid as inhibitor of human topoisomerase II and HeLa cell proliferation. Chem Biol Interact. 2017 Apr 25;268:68-76. doi: 10.1016/j.cbi.2017.02.015. Epub 2017 Feb 28.
8 Transient activation of EGFR/AKT cell survival pathway and expression of survivin contribute to reduced sensitivity of human melanoma cells to betulinic acid. Int J Oncol. 2005 Sep;27(3):823-30.
9 Betulinic acid, a bioactive pentacyclic triterpenoid, inhibits skeletal-related events induced by breast cancer bone metastases and treatment. Toxicol Appl Pharmacol. 2014 Mar 1;275(2):152-62. doi: 10.1016/j.taap.2014.01.009. Epub 2014 Jan 24.
10 Computational investigations of physicochemical, pharmacokinetic, toxicological properties and molecular docking of betulinic acid, a constituent of Corypha taliera (Roxb.) with Phospholipase A2 (PLA2). BMC Complement Altern Med. 2018 Feb 2;18(1):48. doi: 10.1186/s12906-018-2116-x.