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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:3087
CAS Number: 472-15-1
DrugBank ID: DB12480
TTD ID: D0R9YR

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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[3]
Baculoviral IAP repeat-containing protein 5 (BIRC5)	OTILXZYL	BIRC5_HUMAN	Gene/Protein Processing	[4]
Bcl-2 homologous antagonist/killer (BAK1)	OTDP6ILW	BAK_HUMAN	Gene/Protein Processing	[5]
Carbonic anhydrase 9 (CA9)	OTNA51XT	CAH9_HUMAN	Gene/Protein Processing	[6]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[6]
Caspase-7 (CASP7)	OTAPJ040	CASP7_HUMAN	Gene/Protein Processing	[7]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[8]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Gene/Protein Processing	[6]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Gene/Protein Processing	[3]
CCAAT/enhancer-binding protein beta (CEBPB)	OTM9MQIA	CEBPB_HUMAN	Gene/Protein Processing	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

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	Effects and mechanisms of betulinic acid on improving EGFR TKI-resistance of lung cancer cells. Environ Toxicol. 2018 Nov;33(11):1153-1159.
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	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.
6	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.
7	Arsenite-induced apoptosis of human neuroblastoma cells requires p53 but occurs independently of c-Jun. Neuroscience. 2012 Mar 29;206:25-38. doi: 10.1016/j.neuroscience.2012.01.001. Epub 2012 Jan 8.
8	In vitro anticancer activity of Betulinic acid and derivatives thereof on equine melanoma cell lines from grey horses and in vivo safety assessment of the compound NVX-207 in two horses. Chem Biol Interact. 2016 Feb 25;246:20-9. doi: 10.1016/j.cbi.2016.01.002. Epub 2016 Jan 7.
9	Increasing intratumor C/EBP- LIP and nitric oxide levels overcome resistance to doxorubicin in triple negative breast cancer. J Exp Clin Cancer Res. 2018 Nov 27;37(1):286. doi: 10.1186/s13046-018-0967-0.