Details of the Drug

General Information of Drug (ID: DMCMDVR)

Drug Name
Triptolide
Synonyms
triptolide; 38748-32-2; Triptolid; PG490; UNII-19ALD1S53J; NSC 163062; CHEMBL463763; CHEBI:9747; 19ALD1S53J; C20H24O6; PG-490; CPD000466307; Triptolide, Tripterygium wilfordii; (-)-Triptolide; PG 490; Trisoxireno(4b,5:6,7:8a,9)phenanthro(1,2-c)furan-1(3H)-one, 3b,4,4a,6,6a,7a,7b,8b,9,10-decahydro-6-hydroxy-8b-methyl-6a-(1-methylethyl)-, (3bS,4aS,5aS,6R,6aR,7aS,7bS,8aS,8bS)-; SMR000466307; NSC163062; Triptolide, 1; Triptolide(PG490)/; AC1Q6AXN; BSPBio_001595; KBioGR_000315; KBioSS_000315
Indication
Disease Entry ICD 11 Status REF
Autoimmune diabetes 5A10 Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 360.4
Logarithm of the Partition Coefficient (xlogp) 0.2
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C20H24O6
IUPAC Name
(1S,2S,4S,5S,7R,8R,9S,11S,13S)-8-hydroxy-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
Canonical SMILES
CC(C)[C@@]12[C@@H](O1)[C@H]3[C@@]4(O3)[C@]5(CCC6=C([C@@H]5C[C@H]7[C@]4([C@@H]2O)O7)COC6=O)C
InChI
InChI=1S/C20H24O6/c1-8(2)18-13(25-18)14-20(26-14)17(3)5-4-9-10(7-23-15(9)21)11(17)6-12-19(20,24-12)16(18)22/h8,11-14,16,22H,4-7H2,1-3H3/t11-,12-,13-,14-,16+,17-,18-,19+,20+/m0/s1
InChIKey
DFBIRQPKNDILPW-CIVMWXNOSA-N
Cross-matching ID
PubChem CID
107985
ChEBI ID
CHEMBL463763
CAS Number
38748-32-2
UNII
19ALD1S53J
DrugBank ID
DB12025
TTD ID
D0I6LH
INTEDE ID
DR1904
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
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Nuclear factor NF-kappa-B (NFKB) TTSXVID NFKB1_HUMAN ; NFKB2_HUMAN ; TF65_HUMAN ; RELB_HUMAN ; REL_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-binding cassette sub-family C member 4 (ABCC4) OTO27PAL MRP4_HUMAN Gene/Protein Processing [4]
Baculoviral IAP repeat-containing protein 3 (BIRC3) OT3E95KB BIRC3_HUMAN Gene/Protein Processing [5]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [4]
Cyclin-A1 (CCNA1) OTX4HD45 CCNA1_HUMAN Gene/Protein Processing [6]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [4]
Histone H2AX (H2AX) OT18UX57 H2AX_HUMAN Gene/Protein Processing [4]
Histone-lysine N-methyltransferase SUV39H1 (SUV39H1) OTDTF5BU SUV91_HUMAN Gene/Protein Processing [7]
Kelch-like ECH-associated protein 1 (KEAP1) OTFHOD0C KEAP1_HUMAN Gene/Protein Processing [8]
Microtubule-associated proteins 1A/1B light chain 3B (MAP1LC3B) OTUYHB84 MLP3B_HUMAN Gene/Protein Processing [9]
Myc proto-oncogene protein (MYC) OTPV5LUK MYC_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Autoimmune diabetes
ICD Disease Classification 5A10
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 9.85E-01 2.24E-02 7.33E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT02115659) Triptolide-Containing Formulation as Treatment for Autosomal Dominant Polycystic Kidney Disease (ADPKD). U.S. National Institutes of Health.
2 Functional p53 is required for triptolide-induced apoptosis and AP-1 and nuclear factor-kappaB activation in gastric cancer cells. Oncogene. 2001 Nov 29;20(55):8009-18.
3 Preclinical pharmacokinetics of triptolide: a potential antitumor drug. Curr Drug Metab. 2019;20(2):147-154.
4 Variable p53/Nrf2 crosstalk contributes to triptolide-induced hepatotoxic process. Toxicol Lett. 2023 Apr 15;379:67-75. doi: 10.1016/j.toxlet.2023.03.011. Epub 2023 Mar 28.
5 [Study of triptolide-induced apoptosis in MUTZ-1 cells and its allied mechanism]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2005 Jun;13(3):434-9.
6 Triptolide inhibits the growth and metastasis of solid tumors. Mol Cancer Ther. 2003 Jan;2(1):65-72.
7 Triptolide alters histone H3K9 and H3K27 methylation state and induces G0/G1 arrest and caspase-dependent apoptosis in multiple myeloma in vitro. Toxicology. 2010 Jan 12;267(1-3):70-9. doi: 10.1016/j.tox.2009.10.023. Epub 2009 Oct 29.
8 Catalpol and panax notoginseng saponins synergistically alleviate triptolide-induced hepatotoxicity through Nrf2/ARE pathway. Toxicol In Vitro. 2019 Apr;56:141-149. doi: 10.1016/j.tiv.2019.01.016. Epub 2019 Jan 23.
9 High-content analysis boosts identification of the initial cause of triptolide-induced hepatotoxicity. J Appl Toxicol. 2019 Sep;39(9):1337-1347. doi: 10.1002/jat.3821. Epub 2019 Jun 19.