Terpinen-4-ol
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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Identification
- Generic Name
- Terpinen-4-ol
- DrugBank Accession Number
- DB12816
- Background
Terpinen-4-ol is under investigation in clinical trial NCT01647217 (Demodex Blepharitis Treatment Study).
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 154.253
Monoisotopic: 154.1357652 - Chemical Formula
- C10H18O
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAcetylcholinesterase inhibitorHumans UApoptosis regulator Bcl-2 regulatorHumans UE3 ubiquitin-protein ligase XIAP downregulatorHumans UIntestinal-type alkaline phosphatase downregulatorHumans UNuclear factor NF-kappa-B downregulatorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Monoterpenoids
- Direct Parent
- Menthane monoterpenoids
- Alternative Parents
- Monocyclic monoterpenoids / Tertiary alcohols / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homomonocyclic compound / Hydrocarbon derivative / Monocyclic monoterpenoid / Organic oxygen compound / Organooxygen compound / P-menthane monoterpenoid / Tertiary alcohol
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- tertiary alcohol, terpineol (CHEBI:78884) / Menthane monoterpenoids (C17073)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- L65MV77ZG6
- CAS number
- 562-74-3
- InChI Key
- WRYLYDPHFGVWKC-UHFFFAOYSA-N
- InChI
- InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3
- IUPAC Name
- 4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
- SMILES
- CC(C)C1(O)CCC(C)=CC1
References
- General References
- Chooluck K, Singh RP, Sathirakul K, Derendorf H: Plasma and dermal pharmacokinetics of terpinen-4-ol in rats following intravenous administration. Pharmazie. 2013 Feb;68(2):135-40. [Article]
- External Links
- Human Metabolome Database
- HMDB0035833
- KEGG Compound
- C17073
- PubChem Compound
- 11230
- PubChem Substance
- 347828987
- ChemSpider
- 10756
- 1314261
- ChEBI
- 78884
- ChEMBL
- CHEMBL507795
- Wikipedia
- Terpinen-4-ol
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment Seborrheic Blepharitis 1 somestatus stop reason just information to hide 1 Completed Treatment Chronic Blepharitis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.5 mg/mL ALOGPS logP 2.81 ALOGPS logP 2.33 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 20 Chemaxon pKa (Strongest Basic) -0.61 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 48.31 m3·mol-1 Chemaxon Polarizability 18.7 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 137.4944801 predictedDarkChem Lite v0.1.0 [M-H]- 139.22624 predictedDeepCCS 1.0 (2019) [M+H]+ 138.3138801 predictedDarkChem Lite v0.1.0 [M+H]+ 142.33983 predictedDeepCCS 1.0 (2019) [M+Na]+ 137.7049801 predictedDarkChem Lite v0.1.0 [M+Na]+ 151.63728 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsAcetylcholinesterase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Hydrolyzes rapidly the acetylcholine neurotransmitter released into the synaptic cleft allowing to terminate the signal transduction at the neuromuscular junction. Role in neuronal apoptosis
- Specific Function
- acetylcholine binding
- Gene Name
- ACHE
- Uniprot ID
- P22303
- Uniprot Name
- Acetylcholinesterase
- Molecular Weight
- 67795.525 Da
References
- Dohi S, Terasaki M, Makino M: Acetylcholinesterase inhibitory activity and chemical composition of commercial essential oils. J Agric Food Chem. 2009 May 27;57(10):4313-8. doi: 10.1021/jf804013j. Epub 2009 Apr 9. [Article]
2. DetailsApoptosis regulator Bcl-2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Regulator
- General Function
- Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells (PubMed:1508712, PubMed:8183370). Regulates cell death by controlling the mitochondrial membrane permeability (PubMed:11368354). Appears to function in a feedback loop system with caspases (PubMed:11368354). Inhibits caspase activity either by preventing the release of cytochrome c from the mitochondria and/or by binding to the apoptosis-activating factor (APAF-1) (PubMed:11368354). Also acts as an inhibitor of autophagy: interacts with BECN1 and AMBRA1 during non-starvation conditions and inhibits their autophagy function (PubMed:18570871, PubMed:20889974, PubMed:21358617). May attenuate inflammation by impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785)
- Specific Function
- BH domain binding
- Gene Name
- BCL2
- Uniprot ID
- P10415
- Uniprot Name
- Apoptosis regulator Bcl-2
- Molecular Weight
- 26265.66 Da
References
- Wu CS, Chen YJ, Chen JJ, Shieh JJ, Huang CH, Lin PS, Chang GC, Chang JT, Lin CC: Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo. Evid Based Complement Alternat Med. 2012;2012:818261. doi: 10.1155/2012/818261. Epub 2011 Jun 20. [Article]
3. DetailsE3 ubiquitin-protein ligase XIAP
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Downregulator
- General Function
- Multi-functional protein which regulates not only caspases and apoptosis, but also modulates inflammatory signaling and immunity, copper homeostasis, mitogenic kinase signaling, cell proliferation, as well as cell invasion and metastasis (PubMed:11257230, PubMed:11257231, PubMed:11447297, PubMed:12121969, PubMed:12620238, PubMed:17560374, PubMed:17967870, PubMed:19473982, PubMed:20154138, PubMed:22103349, PubMed:9230442). Acts as a direct caspase inhibitor (PubMed:11257230, PubMed:11257231, PubMed:12620238). Directly bind to the active site pocket of CASP3 and CASP7 and obstructs substrate entry (PubMed:11257230, PubMed:11257231, PubMed:16352606, PubMed:16916640). Inactivates CASP9 by keeping it in a monomeric, inactive state (PubMed:12620238). Acts as an E3 ubiquitin-protein ligase regulating NF-kappa-B signaling and the target proteins for its E3 ubiquitin-protein ligase activity include: RIPK1, RIPK2, MAP3K2/MEKK2, DIABLO/SMAC, AIFM1, CCS, PTEN and BIRC5/survivin (PubMed:17560374, PubMed:17967870, PubMed:19473982, PubMed:20154138, PubMed:22103349, PubMed:22607974, PubMed:29452636, PubMed:30026309). Acts as an important regulator of innate immunity by mediating 'Lys-63'-linked polyubiquitination of RIPK2 downstream of NOD1 and NOD2, thereby transforming RIPK2 into a scaffolding protein for downstream effectors, ultimately leading to activation of the NF-kappa-B and MAP kinases signaling (PubMed:19667203, PubMed:22607974, PubMed:29452636, PubMed:30026309). 'Lys-63'-linked polyubiquitination of RIPK2 also promotes recruitment of the LUBAC complex to RIPK2 (PubMed:22607974, PubMed:29452636). Regulates the BMP signaling pathway and the SMAD and MAP3K7/TAK1 dependent pathways leading to NF-kappa-B and JNK activation (PubMed:17560374). Ubiquitination of CCS leads to enhancement of its chaperone activity toward its physiologic target, SOD1, rather than proteasomal degradation (PubMed:20154138). Ubiquitination of MAP3K2/MEKK2 and AIFM1 does not lead to proteasomal degradation (PubMed:17967870, PubMed:22103349). Plays a role in copper homeostasis by ubiquitinating COMMD1 and promoting its proteasomal degradation (PubMed:14685266). Can also function as E3 ubiquitin-protein ligase of the NEDD8 conjugation pathway, targeting effector caspases for neddylation and inactivation (PubMed:21145488). Ubiquitinates and therefore mediates the proteasomal degradation of BCL2 in response to apoptosis (PubMed:29020630). Protects cells from spontaneous formation of the ripoptosome, a large multi-protein complex that has the capability to kill cancer cells in a caspase-dependent and caspase-independent manner (PubMed:22095281). Suppresses ripoptosome formation by ubiquitinating RIPK1 and CASP8 (PubMed:22095281). Acts as a positive regulator of Wnt signaling and ubiquitinates TLE1, TLE2, TLE3, TLE4 and AES (PubMed:22304967). Ubiquitination of TLE3 results in inhibition of its interaction with TCF7L2/TCF4 thereby allowing efficient recruitment and binding of the transcriptional coactivator beta-catenin to TCF7L2/TCF4 that is required to initiate a Wnt-specific transcriptional program (PubMed:22304967)
- Specific Function
- cysteine-type endopeptidase inhibitor activity
- Gene Name
- XIAP
- Uniprot ID
- P98170
- Uniprot Name
- E3 ubiquitin-protein ligase XIAP
- Molecular Weight
- 56684.41 Da
References
- Wu CS, Chen YJ, Chen JJ, Shieh JJ, Huang CH, Lin PS, Chang GC, Chang JT, Lin CC: Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo. Evid Based Complement Alternat Med. 2012;2012:818261. doi: 10.1155/2012/818261. Epub 2011 Jun 20. [Article]
4. DetailsIntestinal-type alkaline phosphatase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Downregulator
- General Function
- Alkaline phosphatase that can hydrolyze various phosphate compounds
- Specific Function
- alkaline phosphatase activity
- Gene Name
- ALPI
- Uniprot ID
- P09923
- Uniprot Name
- Intestinal-type alkaline phosphatase
- Molecular Weight
- 56811.695 Da
References
- Wu CS, Chen YJ, Chen JJ, Shieh JJ, Huang CH, Lin PS, Chang GC, Chang JT, Lin CC: Terpinen-4-ol Induces Apoptosis in Human Nonsmall Cell Lung Cancer In Vitro and In Vivo. Evid Based Complement Alternat Med. 2012;2012:818261. doi: 10.1155/2012/818261. Epub 2011 Jun 20. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Downregulator
- General Function
- NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related to many biological processes such as inflammation, immunity, differentiation, cell growth, tumorigenesis and apoptosis. NF-kappa-B is a homo- or heterodimeric complex formed by the Rel-like domain-containing proteins RELA/p65, RELB, NFKB1/p105, NFKB1/p50, REL and NFKB2/p52. The dimers bind at kappa-B sites in the DNA of their target genes and the individual dimers have distinct preferences for different kappa-B sites that they can bind with distinguishable affinity and specificity. Different dimer combinations act as transcriptional activators or repressors, respectively. NF-kappa-B is controlled by various mechanisms of post-translational modification and subcellular compartmentalization as well as by interactions with other cofactors or corepressors. NF-kappa-B complexes are held in the cytoplasm in an inactive state complexed with members of the NF-kappa-B inhibitor (I-kappa-B) family. In a conventional activation pathway, I-kappa-B is phosphorylated by I-kappa-B kinases (IKKs) in response to different activators, subsequently degraded thus liberating the active NF-kappa-B complex which translocates to the nucleus. In a non-canonical activation pathway, the MAP3K14-activated CHUK/IKKA homodimer phosphorylates NFKB2/p100 associated with RelB, inducing its proteolytic processing to NFKB2/p52 and the formation of NF-kappa-B RelB-p52 complexes. The NF-kappa-B heterodimeric RelB-p52 complex is a transcriptional activator. The NF-kappa-B p52-p52 homodimer is a transcriptional repressor. NFKB2 appears to have dual functions such as cytoplasmic retention of attached NF-kappa-B proteins by p100 and generation of p52 by a cotranslational processing. The proteasome-mediated process ensures the production of both p52 and p100 and preserves their independent function. p52 binds to the kappa-B consensus sequence 5'-GGRNNYYCC-3', located in the enhancer region of genes involved in immune response and acute phase reactions. p52 and p100 are respectively the minor and major form; the processing of p100 being relatively poor. Isoform p49 is a subunit of the NF-kappa-B protein complex, which stimulates the HIV enhancer in synergy with p65. In concert with RELB, regulates the circadian clock by repressing the transcriptional activator activity of the CLOCK-BMAL1 heterodimer
- Specific Function
- DNA-binding transcription activator activity, RNA polymerase II-specific
Components:
Name | UniProt ID |
---|---|
Nuclear factor NF-kappa-B p100 subunit | Q00653 |
Nuclear factor NF-kappa-B p105 subunit | P19838 |
References
- Chaiyana W, Anuchapreeda S, Leelapornpisid P, Phongpradist R, Viernstein H, Mueller M: Development of Microemulsion Delivery System of Essential Oil from Zingiber cassumunar Roxb. Rhizome for Improvement of Stability and Anti-Inflammatory Activity. AAPS PharmSciTech. 2017 May;18(4):1332-1342. doi: 10.1208/s12249-016-0603-2. Epub 2016 Aug 8. [Article]
Enzymes
1. DetailsCytochrome P450 2A6
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- Miyazawa M, Haigou R: Determination of cytochrome P450 enzymes involved in the metabolism of (-)-terpinen-4-ol by human liver microsomes. Xenobiotica. 2011 Dec;41(12):1056-62. doi: 10.3109/00498254.2011.596230. [Article]
Drug created at October 21, 2016 00:28 / Updated at June 27, 2022 17:21