O-PHENYLPHENOL

Relevant Data

Food Additives Approved by WHO:

General Information

MaintermO-PHENYLPHENOL
Doc TypeEAF
CAS Reg.No.(or other ID)90-43-7
Regnum 175.105
177.2600
176.210
178.1010
177.1632

From www.fda.gov

Computed Descriptors

Download SDF
2D Structure
CID7017
IUPAC Name2-phenylphenol
InChIInChI=1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H
InChI KeyLLEMOWNGBBNAJR-UHFFFAOYSA-N
Canonical SMILESC1=CC=C(C=C1)C2=CC=CC=C2O
Molecular FormulaC12H10O
Wikipedia2-phenylphenol

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight170.211
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Complexity149.0
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 O A O g A A A A A A I A A A A A A A A A B A A A A A A A A A A A A = =
Topological Polar Surface Area20.2
Monoisotopic Mass170.073
Exact Mass170.073
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count13
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem

Food Additives Biosynthesis/Degradation

ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9459
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.9127
P-glycoprotein SubstrateNon-substrate0.7749
P-glycoprotein InhibitorNon-inhibitor0.8914
Non-inhibitor0.9499
Renal Organic Cation TransporterNon-inhibitor0.8475
Distribution
Subcellular localizationMitochondria0.8971
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7297
CYP450 2D6 SubstrateNon-substrate0.8420
CYP450 3A4 SubstrateNon-substrate0.6973
CYP450 1A2 InhibitorInhibitor0.8690
CYP450 2C9 InhibitorInhibitor0.6231
CYP450 2D6 InhibitorNon-inhibitor0.9473
CYP450 2C19 InhibitorInhibitor0.8429
CYP450 3A4 InhibitorNon-inhibitor0.9628
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.7255
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9087
Non-inhibitor0.8603
AMES ToxicityNon AMES toxic0.9325
CarcinogensNon-carcinogens0.7817
Fish ToxicityHigh FHMT0.9677
Tetrahymena Pyriformis ToxicityHigh TPT0.9884
Honey Bee ToxicityHigh HBT0.7398
BiodegradationNot ready biodegradable0.7893
Acute Oral ToxicityIII0.8400
Carcinogenicity (Three-class)Non-required0.5193

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-2.9306LogS
Caco-2 Permeability1.7139LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9614LD50, mol/kg
Fish Toxicity0.6640pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.2152pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureNone
Mechanism of ToxicityNone
MetabolismNone
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans.
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  1. Shen DT, Crawford TB, Gorham JR, McGuire TC: Inactivation of equine infectious anemia virus by chemical disinfectants. Am J Vet Res. 1977 Aug;38(8):1217-9.[199094 ]
  2. Johnson GD, Harsy SG, Geronimo J, Wise JM: Orthophenylphenol and phenylhydroquinone residues in citrus fruit and processed citrus products after postharvest fungicidal treatments with sodium orthophenylphenate in California and Florida. J Agric Food Chem. 2001 May;49(5):2497-502.[11368626 ]
  3. Humphreys MJ, Allman R, Lloyd D: Determination of the viability of Trichomonas vaginalis using flow cytometry. Cytometry. 1994 Apr 1;15(4):343-8.[8026224 ]
  4. HOPKINS EF, LOUCKS KW: Prevention of the phytotoxic action of sodium orthophenylphenate on citrus fruits by hexamine. Science. 1950 Dec 15;112(2920):720-1.[14787507 ]
  5. Diaz Borras A, Vila Aguilar R, Hernandez Gimenez E: Synergistic effect of fungicides on resistant strains of Penicillium italicum and Penicillium digitatum. Int J Food Microbiol. 1988 Aug;7(1):79-85.[3275313 ]
  6. Csermely P, Balint E, Grimley PM, Aszalos A: Protein kinase C is involved in the early signals of interferon-alpha but not of interferon-gamma in U937 cells. J Interferon Res. 1990 Dec;10(6):605-11.[2128303 ]
  7. Reitz RH, Fox TR, Quast JF, Hermann EA, Watanabe PG: Biochemical factors involved in the effects of orthophenylphenol (OPP) and sodium orthophenylphenate (SOPP) on the urinary tract of male F344 rats. Toxicol Appl Pharmacol. 1984 Apr;73(2):345-9.[6710533 ]
  8. Cinelli AR, Salzberg BM: Dendritic origin of late events in optical recordings from salamander olfactory bulb. J Neurophysiol. 1992 Sep;68(3):786-806.[1432048 ]
  9. Evans JA, Darlington DN, Gann DS: A circulating factor(s) mediates cell depolarization in hemorrhagic shock. Ann Surg. 1991 Jun;213(6):549-56; discussion 556-7.[2039285 ]
  10. Fangstrom B, Hovander L, Bignert A, Athanassiadis I, Linderholm L, Grandjean P, Weihe P, Bergman A: Concentrations of polybrominated diphenyl ethers, polychlonnated biphenyls, and polychlorobiphenylols in serum from pregnant Faroese women and their children 7 years later. Environ Sci Technol. 2005 Dec 15;39(24):9457-63.[16475322 ]
  11. McDONOUGH ES: Inhibition of mold contamination in Drosophila food using sodium orthophenylphenate. Science. 1953 Oct 2;118(3066):388.[13101762 ]
  12. Santhamma KR, Bhaduri A: Characterization of the respiratory chain of Leishmania donovani promastigotes. Mol Biochem Parasitol. 1995 Dec;75(1):43-53.[8720174 ]
  13. Calori-Domingues MA, Fonseca H: Laboratory evaluation of chemical control of aflatoxin production in unshelled peanuts (Arachis hypogaea L.). Food Addit Contam. 1995 May-Jun;12(3):347-50.[7664926 ]
  14. Ranzani MR, Fonseca H: Mycological evaluation of chemically-treated unshelled peanuts. Food Addit Contam. 1995 May-Jun;12(3):343-6.[7664925 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBiphenyls and derivatives
Intermediate Tree NodesNot available
Direct ParentBiphenyls and derivatives
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBiphenyl - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis 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

Target Details

Bcl-2-like protein 1

General Function:
Protein kinase binding
Specific Function:
Potent inhibitor of cell death. Inhibits activation of caspases. Appears to regulate cell death by blocking the voltage-dependent anion channel (VDAC) by binding to it and preventing the release of the caspase activator, CYC1, from the mitochondrial membrane. Also acts as a regulator of G2 checkpoint and progression to cytokinesis during mitosis.Isoform Bcl-X(L) also regulates presynaptic plasticity, including neurotransmitter release and recovery, number of axonal mitochondria as well as size and number of synaptic vesicle clusters. During synaptic stimulation, increases ATP availability from mitochondria through regulation of mitochondrial membrane ATP synthase F(1)F(0) activity and regulates endocytic vesicle retrieval in hippocampal neurons through association with DMN1L and stimulation of its GTPase activity in synaptic vesicles. May attenuate inflammation impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785).Isoform Bcl-X(S) promotes apoptosis.
Gene Name:
BCL2L1
Uniprot ID:
Q07817
Molecular Weight:
26048.8 Da
References
  1. Barelier S, Pons J, Marcillat O, Lancelin JM, Krimm I: Fragment-based deconstruction of Bcl-xL inhibitors. J Med Chem. 2010 Mar 25;53(6):2577-88. doi: 10.1021/jm100009z. [20192224 ]
Target Details

P2Y purinoceptor 1

General Function:
Scaffold protein binding
Specific Function:
Receptor for extracellular adenine nucleotides such as ATP and ADP. In platelets binding to ADP leads to mobilization of intracellular calcium ions via activation of phospholipase C, a change in platelet shape, and probably to platelet aggregation.
Gene Name:
P2RY1
Uniprot ID:
P47900
Molecular Weight:
42071.08 Da
References
  1. 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 ]
Target Details

Peroxisome proliferator-activated receptor alpha

General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular Weight:
52224.595 Da
References
  1. 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 ]
Target Details

Prostaglandin E2 receptor EP2 subtype

General Function:
Prostaglandin e receptor activity
Specific Function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
Gene Name:
PTGER2
Uniprot ID:
P43116
Molecular Weight:
39759.945 Da
References
  1. 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 ]
Target Details

Cytochrome P450 2B6

General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. 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