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
CHEBI:3086
CAS Number
473-98-3
TTD ID
D05KJY

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
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) OTRT3F3U HMDH_HUMAN Gene/Protein Processing [2]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [3]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [4]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Protein Interaction/Cellular Processes [5]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Protein Interaction/Cellular Processes [5]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Protein Interaction/Cellular Processes [5]
Epidermal growth factor receptor (EGFR) OTAPLO1S EGFR_HUMAN Post-Translational Modifications [6]
Eukaryotic translation initiation factor 4E-binding protein 1 (EIF4EBP1) OTHBQVD5 4EBP1_HUMAN Post-Translational Modifications [5]
Fatty acid synthase (FASN) OTFII9KG FAS_HUMAN Gene/Protein Processing [2]
Glucose-6-phosphatase catalytic subunit 1 (G6PC1) OTJ6FM9F G6PC1_HUMAN Gene/Protein Processing [7]
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 Fatostatin inhibits cancer cell proliferation by affecting mitotic microtubule spindle assembly and cell division. J Biol Chem. 2016 Aug 12;291(33):17001-8.
3 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.
4 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.
5 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.
6 Inhibition of SREBP increases gefitinib sensitivity in non-small cell lung cancer cells. Oncotarget. 2016 Aug 9;7(32):52392-52403.
7 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.