Details of the Drug

General Information of Drug (ID: DMEDGKO)

Drug Name
dibutyl phthalate
Synonyms di-n-butyl phthalate; n-butyl phthalate; nutyl phthalate
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
ATC Code
P03BX03: dibutyl phthalate
P03BX: Other insecticides and repellents
P03B: INSECTICIDES AND REPELLENTS
P03: ECTOPARASITICIDES, INCL. SCABICIDES, INSECTICIDES AND REPELLENTS
P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 278.34
Logarithm of the Partition Coefficient (xlogp) 4.7
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C16H22O4
IUPAC Name
dibutyl benzene-1,2-dicarboxylate
Canonical SMILES
CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC
InChI
InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3
InChIKey
DOIRQSBPFJWKBE-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3026
ChEBI ID
CHEMBL272485
CAS Number
84-74-2
UNII
2286E5R2KE
DrugBank ID
DB13716
TTD ID
D07FLG
INTEDE ID
DR0481
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Transformation-sensitive protein p120 (TRPA1) TTELV3W TRPA1_HUMAN Activator [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1B1 (CYP1B1)
Main DME 		DE9QHP6 CP1B1_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5'-AMP-activated protein kinase catalytic subunit alpha-2 (PRKAA2) OTU1KZPV AAPK2_HUMAN Gene/Protein Processing [4]
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [5]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [6]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [7]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [8]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Protein Interaction/Cellular Processes [8]
Cell division cycle-associated protein 3 (CDCA3) OTUI8QK3 CDCA3_HUMAN Gene/Protein Processing [9]
Centrosomal protein of 55 kDa (CEP55) OTGSG2PA CEP55_HUMAN Gene/Protein Processing [9]
Cocaine esterase (CES2) OTC647SQ EST2_HUMAN Biotransformations [10]
Creatine kinase U-type, mitochondrial (CKMT1A) OTCINHH5 KCRU_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) 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: 6295).
2 TRPA1 and TRPV1 activation is a novel adjuvant effect mechanism in contact hypersensitivity. J Neuroimmunol. 2009 Feb 15;207(1-2):66-74.
3 Inhibition of human cytochrome p450 1b1 further clarifies its role in the activation of dibenzo[a,l]pyrene in cells in culture. J Biochem Mol Toxicol. 2007;21(3):101-9.
4 Dibutyl phthalate induces epithelial-mesenchymal transition of renal tubular epithelial cells via the Ang II/AMPK2/Cx43 signaling pathway. Toxicology. 2023 Aug 1;494:153584. doi: 10.1016/j.tox.2023.153584. Epub 2023 Jun 24.
5 Application of oligonucleotide microarray technology to toxic occupational exposures. J Toxicol Environ Health A. 2008;71(5):315-24.
6 In Vitro Exposure of Human Luteinized Mural Granulosa Cells to Dibutyl Phthalate Affects Global Gene Expression. Toxicol Sci. 2017 Nov 1;160(1):180-188. doi: 10.1093/toxsci/kfx170.
7 Di-n-butyl phthalate promotes monocyte recruitment via miR-137-3p-SP1-MCP-1 pathway. Ecotoxicol Environ Saf. 2022 May 1;236:113491. doi: 10.1016/j.ecoenv.2022.113491. Epub 2022 Apr 6.
8 Phthalates stimulate the epithelial to mesenchymal transition through an HDAC6-dependent mechanism in human breast epithelial stem cells. Toxicol Sci. 2012 Aug;128(2):365-76. doi: 10.1093/toxsci/kfs163. Epub 2012 May 2.
9 In silico, in vitro and in vivo studies: Dibutyl phthalate promotes prostate cancer cell proliferation by activating Forkhead Box M1 and remission after Natura- pretreatment. Toxicology. 2023 Apr;488:153465. doi: 10.1016/j.tox.2023.153465. Epub 2023 Feb 23.
10 Hydrolysis of dibutyl phthalate and di(2-ethylhexyl) phthalate in human liver, small intestine, kidney, and lung: An in vitro analysis using organ subcellular fractions and recombinant carboxylesterases. Chem Biol Interact. 2023 Feb 25;372:110353. doi: 10.1016/j.cbi.2023.110353. Epub 2023 Jan 16.