Details of the Drug

General Information of Drug (ID: DMGQRON)

Drug Name
BETULIN
Synonyms
Betulin; 473-98-3; Betulinol; Betuline; Trochol; Lup-20(29)-ene-3b,28-diol; Betulol; Lup-20(29)-ene-3beta,28-diol; UNII-6W70HN7X7O; NSC 4644; C30H50O2; EINECS 207-475-5; Lup-20(30)-ene-3beta,28-diol; AI3-62999; CHEBI:3086; 6W70HN7X7O; Lup-20(29)-ene-3,28-diol, (3beta)-; (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol; Betulinic alcohol; lup-20(29)-ene-3 beta,28-diol
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) 442.7
Logarithm of the Partition Coefficient (xlogp) 8.3
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C30H50O2
IUPAC Name
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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]chrysen-9-ol
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)CO
InChI
InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
InChIKey
FVWJYYTZTCVBKE-ROUWMTJPSA-N
Cross-matching ID
PubChem CID
72326
ChEBI ID
CHEMBL23236
CAS Number
473-98-3
UNII
6W70HN7X7O
DrugBank ID
DB16890
TTD ID
D05KJY
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
Glycogen phosphorylase muscle form (GP) TTZHY6R PYGM_HUMAN Inhibitor [1]

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 [2]
Glucose-6-phosphatase catalytic subunit 1 (G6PC1) OTJ6FM9F G6PC1_HUMAN Gene/Protein Processing [3]
Hydroxymethylglutaryl-CoA synthase, cytoplasmic (HMGCS1) OTCO26FV HMCS1_HUMAN Gene/Protein Processing [4]
MARVEL domain-containing protein 1 (MARVELD1) OT5CPOJE MALD1_HUMAN Gene/Protein Processing [5]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [6]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [6]
Phosphoenolpyruvate carboxykinase, cytosolic (PCK1) OTNWEJ5Y PCKGC_HUMAN Gene/Protein Processing [3]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [7]
Stearoyl-CoA desaturase (SCD) OTB1073G SCD_HUMAN Gene/Protein Processing [4]
UDP-glucuronosyltransferase 1A3 OTUEOER3 UD13_HUMAN Biotransformations [8]
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
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 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.
2 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.
3 Anti-inflammatory action of betulin and its potential as a dissociated glucocorticoid receptor modulator. Food Chem Toxicol. 2021 Nov;157:112539. doi: 10.1016/j.fct.2021.112539. Epub 2021 Sep 7.
4 Fatostatin inhibits cancer cell proliferation by affecting mitotic microtubule spindle assembly and cell division. J Biol Chem. 2016 Aug 12;291(33):17001-8.
5 Inhibition of SREBP increases gefitinib sensitivity in non-small cell lung cancer cells. Oncotarget. 2016 Aug 9;7(32):52392-52403.
6 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.
7 Betulin inhibits mTOR and induces autophagy to promote apoptosis in human osteosarcoma cell lines. Environ Toxicol. 2020 Aug;35(8):879-887. doi: 10.1002/tox.22924. Epub 2020 Mar 19.
8 Phase II metabolism of betulin by rat and human UDP-glucuronosyltransferases and sulfotransferases. Chem Biol Interact. 2019 Apr 1;302:190-195. doi: 10.1016/j.cbi.2019.02.009. Epub 2019 Feb 15.