4-PHENYLPHENOL
General Information
| Mainterm | 4-PHENYLPHENOL |
| CAS Reg.No.(or other ID) | 92-69-3 |
| Regnum |
175.300 177.2600 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 7103 |
| IUPAC Name | 4-phenylphenol |
| InChI | InChI=1S/C12H10O/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,13H |
| InChI Key | YXVFYQXJAXKLAK-UHFFFAOYSA-N |
| Canonical SMILES | C1=CC=C(C=C1)C2=CC=C(C=C2)O |
| Molecular Formula | C12H10O |
| Wikipedia | 4-biphenylol |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 170.211 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Complexity | 141.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B w I A A A A A A A A A A A A A A A A A A A A A A A A A A w Y A A A A A A A A A A B Q A A A G g A A C A A A D A S A m A A w B o A A A g C A A i B C A A A C A A A g I A A I i A A G C I g I J i K C E R K A c A A k w B E I m A e A w P A O o A A A A A A A A A B A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 20.2 |
| Monoisotopic Mass | 170.073 |
| Exact Mass | 170.073 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9122 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8995 |
| P-glycoprotein Substrate | Non-substrate | 0.7782 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9372 |
| Non-inhibitor | 0.9394 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8445 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8364 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7452 |
| CYP450 2D6 Substrate | Non-substrate | 0.9151 |
| CYP450 3A4 Substrate | Non-substrate | 0.7109 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8034 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6738 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9665 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6003 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9278 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5529 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9068 |
| Non-inhibitor | 0.9019 | |
| AMES Toxicity | Non AMES toxic | 0.8731 |
| Carcinogens | Non-carcinogens | 0.7267 |
| Fish Toxicity | High FHMT | 0.9550 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9904 |
| Honey Bee Toxicity | High HBT | 0.7889 |
| Biodegradation | Not ready biodegradable | 0.7510 |
| Acute Oral Toxicity | III | 0.8644 |
| Carcinogenicity (Three-class) | Non-required | 0.4885 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7753 | LogS |
| Caco-2 Permeability | 1.6237 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7117 | LD50, mol/kg |
| Fish Toxicity | 0.8768 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.3778 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | |
|---|---|
| Mechanism of Toxicity | |
| Metabolism | |
| Toxicity Values | |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | |
| Health Effects | |
| Treatment | |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Biphenyls and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Biphenyls and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Biphenyl - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. |
From ClassyFire
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EIF2AK3/PERK. May play an important role in CKII- and p60c-src-induced signal transduction cascades. May regulate the EFNA5-EPHA3 signaling pathway which modulates cell reorganization and cell-cell repulsion. May also regulate the hepatocyte growth factor receptor signaling pathway through dephosphorylation of MET.
- Gene Name:
- PTPN1
- Uniprot ID:
- P18031
- Molecular Weight:
- 49966.44 Da
References
- Cross KP, Myatt G, Yang C, Fligner MA, Verducci JS, Blower PE Jr: Finding discriminating structural features by reassembling common building blocks. J Med Chem. 2003 Oct 23;46(22):4770-5. [14561096 ]
- General Function:
- Vascular endothelial growth factor receptor binding
- Specific Function:
- Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of blood vessels. Binds to the FLT1/VEGFR1 and KDR/VEGFR2 receptors, heparan sulfate and heparin. NRP1/Neuropilin-1 binds isoforms VEGF-165 and VEGF-145. Isoform VEGF165B binds to KDR but does not activate downstream signaling pathways, does not activate angiogenesis and inhibits tumor growth.
- Gene Name:
- VEGFA
- Uniprot ID:
- P15692
- Molecular Weight:
- 27042.205 Da
References
- Hajduk PJ, Bures M, Praestgaard J, Fesik SW: Privileged molecules for protein binding identified from NMR-based screening. J Med Chem. 2000 Sep 7;43(18):3443-7. [10978192 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial membrane potential and cellular respiration upon stimulation by progesterone.
- Gene Name:
- PGR
- Uniprot ID:
- P06401
- Molecular Weight:
- 98979.96 Da
References
- Li J, Ma M, Wang Z: In vitro profiling of endocrine disrupting effects of phenols. Toxicol In Vitro. 2010 Feb;24(1):201-7. doi: 10.1016/j.tiv.2009.09.008. Epub 2009 Sep 16. [19765641 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
- Gene Name:
- MMP3
- Uniprot ID:
- P08254
- Molecular Weight:
- 53976.84 Da
References
- Erlanson DA, McDowell RS, O'Brien T: Fragment-based drug discovery. J Med Chem. 2004 Jul 1;47(14):3463-82. [15214773 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Cholesterol binding
- Specific Function:
- Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
- Gene Name:
- TSPO
- Uniprot ID:
- P30536
- Molecular Weight:
- 18827.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
From T3DB