Details of the Drug

General Information of Drug (ID: DM4ZLUH)

Drug Name

LUPEOL

Synonyms

Fagarsterol; Lupenol; EINECS 208-889-9; NSC 90487; (3-beta)-Lup-20(29)-en-3-ol; Lup-20(29)-en-3-ol, (3beta)-; (1R,3aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol; Lup-20(29)-en-3-ol; Lup-20(29)-en-3-beta-ol; Lup-20(29)-en-3-ol, (3-beta)-; Lup-20(29)-en-3-ol, (3.beta.)-; AC1L2J5Q; SCHEMBL561024; Lup-20(29)-en-3beta-ol; LS-88199; AN-14996

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

426.7

Logarithm of the Partition Coefficient (xlogp)

9.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C30H50O
IUPAC Name: (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-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)C
InChI: InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
InChIKey: MQYXUWHLBZFQQO-QGTGJCAVSA-N

Cross-matching ID

PubChem CID: 259846
ChEBI ID: CHEBI:6570
CAS Number: 545-47-1
DrugBank ID: DB12622
TTD ID: D0RA6H

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
DNA topoisomerase II (TOP2)	TT0IHXV	TOP2A_HUMAN ; TOP2B_HUMAN	Inhibitor	[1]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[2]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[2]
Cadherin-1 (CDH1)	OTFJMXPM	CADH1_HUMAN	Gene/Protein Processing	[3]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[2]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[2]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Gene/Protein Processing	[2]
Interleukin-1 beta (IL1B)	OT0DWXXB	IL1B_HUMAN	Gene/Protein Processing	[3]
Interleukin-10 (IL10)	OTIRFRXC	IL10_HUMAN	Gene/Protein Processing	[3]
Interleukin-6 (IL6)	OTUOSCCU	IL6_HUMAN	Gene/Protein Processing	[3]
Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase and dual-specificity protein phosphatase PTEN (PTEN)	OTOWDUNT	PTEN_HUMAN	Gene/Protein Processing	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity. J Nat Prod. 2001 Dec;64(12):1545-7.
2	Geraniol and lupeol inhibit growth and promote apoptosis in human hepatocarcinoma cells through the MAPK signaling pathway. J Cell Biochem. 2019 Apr;120(4):5033-5041. doi: 10.1002/jcb.27779. Epub 2018 Dec 2.
3	Paederia foetida induces anticancer activity by modulating chromatin modification enzymes and altering pro-inflammatory cytokine gene expression in human prostate cancer cells. Food Chem Toxicol. 2019 Aug;130:161-173. doi: 10.1016/j.fct.2019.05.016. Epub 2019 May 18.
4	Lupeol targets liver tumor-initiating cells through phosphatase and tensin homolog modulation. Hepatology. 2011 Jan;53(1):160-70. doi: 10.1002/hep.24000. Epub 2010 Oct 26.