Details of the Drug

General Information of Drug (ID: DM2L3PE)

Drug Name
Hyperforin
Synonyms
hyperforin; 11079-53-1; hyperforine; hiperforina; UNII-RM741E34FP; CHEBI:5834; RM741E34FP; CHEMBL1237210; (1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione; (1R,5S,6R,7S)-4-hydroxy-5-isobutyryl-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione; HSDB 7646; (+)-Hyperforin; Spectrum5_002025; SCHEMBL98723; CHEMBL501711; GTPL2764; SCHEMBL15557965; Hyperforin, &gt
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): 3 Molecular Weight (mw) 536.8
Logarithm of the Partition Coefficient (xlogp) 9.6
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in 9 hours [2]
Chemical Identifiers
Formula
C35H52O4
IUPAC Name
(1R,5R,7S,8R)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione
Canonical SMILES
CC(C)C(=O)[C@]12C(=O)C(=C([C@](C1=O)(C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C
InChI
InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1
InChIKey
KGSZHKRKHXOAMG-HQKKAZOISA-N
Cross-matching ID
PubChem CID
441298
ChEBI ID
CHEMBL5834
CAS Number
11079-53-1
UNII
RM741E34FP
DrugBank ID
DB01892
TTD ID
D09VTJ
VARIDT ID
DR00582
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Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Arachidonate 5-lipoxygenase (5-LOX) TT2J34L LOX5_HUMAN Inhibitor [3]
Pregnane X receptor (NR1I2) TT7LCTF NR1I2_HUMAN Binder [4]
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1) OTG2T749 CP24A_HUMAN Gene/Protein Processing [5]
5-aminolevulinate synthase, non-specific, mitochondrial (ALAS1) OTQY6ZSF HEM1_HUMAN Gene/Protein Processing [6]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [6]
Bcl-2 homologous antagonist/killer (BAK1) OTDP6ILW BAK_HUMAN Gene/Protein Processing [7]
CASP8 and FADD-like apoptosis regulator (CFLAR) OTX14BAS CFLAR_HUMAN Gene/Protein Processing [7]
Cytochrome c (CYCS) OTBFALJD CYC_HUMAN Gene/Protein Processing [8]
E3 ubiquitin-protein ligase XIAP OT24GP9B XIAP_HUMAN Gene/Protein Processing [7]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [9]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [7]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [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
Prostaglandin G/H synthase 1 (COX-1) DTT PTGS1 3.97E-03 0.16 0.43
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression 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: 2764).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Hyperforin is a dual inhibitor of cyclooxygenase-1 and 5-lipoxygenase. Biochem Pharmacol. 2002 Dec 15;64(12):1767-75.
4 Pregnane X receptor (PXR) regulates P-glycoprotein at the blood-brain barrier: functional similarities between pig and human PXR. J Pharmacol Exp Ther. 2009 Apr;329(1):141-9.
5 Possible involvement of pregnane X receptor-enhanced CYP24 expression in drug-induced osteomalacia. J Clin Invest. 2005 Jan;115(1):177-86.
6 No activation of human pregnane X receptor by hyperforin-related phloroglucinols. J Pharmacol Exp Ther. 2014 Mar;348(3):393-400.
7 Hyperforin induces apoptosis through extrinsic/intrinsic pathways and inhibits EGFR/ERK/NF-B-mediated anti-apoptotic potential in glioblastoma. Environ Toxicol. 2020 Oct;35(10):1058-1069. doi: 10.1002/tox.22942. Epub 2020 Jun 2.
8 Neuroprotective role of hyperforin on aluminum maltolate-induced oxidative damage and apoptosis in PC12 cells and SH-SY5Y cells. Chem Biol Interact. 2019 Feb 1;299:15-26. doi: 10.1016/j.cbi.2018.11.016. Epub 2018 Nov 24.
9 Hyperforin, the active component of St. John's wort, induces IL-8 expression in human intestinal epithelial cells via a MAPK-dependent, NF-kappaB-independent pathway. J Clin Immunol. 2004 Nov;24(6):623-36. doi: 10.1007/s10875-004-6248-z.