T3DB: 2-Biphenylol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (5)XML

Targets (5)

Record Information

Version

2.0

Creation Date

2014-08-29 04:48:33 UTC

Update Date

2014-12-24 20:26:35 UTC

Accession Number

T3D3981

Identification

Common Name

2-Biphenylol

Class

Small Molecule

Description

2-Biphenylol is found in lemon. It is an antifungal agent and preservative. 2-Biphenylol is used for post-harvest control of storage disease in apples, citrus fruit, stone fruit, tomatoes, cucumber and peppers through the use of impregnated wrapping materials or by direct application in a wax. 2-Biphenylol is used in food seasonings. Inhibitory to a wider range of moulds than Biphenyl HMJ12-A. The practical way of treatment is to immerse citrus fruit in an alkaline aqueous solution of the parent compound or its Na salt. 2-Biphenylol belongs to the family of Biphenyls and Derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Compound Type

Food Additive
Food Toxin
Household Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin
Preservative

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
(1,1'-Biphenyl)-2-ol
(1,1-Biphenyl)-2-ol
1,1'-Biphenyl-2-ol
1-Hydroxy-2-phenylbenzene
2-Fenylfenol
2-Hydroxy biphenyl
2-Hydroxy-1,1'-biphenyl
2-Hydroxybiphenyl
2-Hydroxydiphenyl
2-Phenylphenol, BSI, ISO
Biphenylol
Dowicide 1
E231
FEMA 3959
HBP
Hydroxdiphenyl
Hydroxy-2-phenylbenzene
Hydroxybiphenyl
Manusept
Nectryl
Nipacide OPP
O-Biphenylol
O-Diphenylol
O-Hydroxybiphenyl
O-Hydroxydiphenyl
O-Phenyl phenol
O-Phenylphenate
O-Phenylphenol
O-Xenol
O-Xonal
OPP?
Ortho-phenylphenate
Ortho-phenylphenol
Orthohydroxydipbenyl
Orthohydroxydiphenyl
Orthophenylphenol
Orthoxenol
Phenylphenol
Rotoline
Stellisept
Torsite

Chemical Formula

C₁₂H₁₀O

Average Molecular Mass

170.207 g/mol

Monoisotopic Mass

170.073 g/mol

CAS Registry Number

90-43-7

IUPAC Name

[1,1'-biphenyl]-2-ol

Traditional Name

o-phenylphenol

SMILES

OC1=CC=CC=C1C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H

InChI Key

InChIKey=LLEMOWNGBBNAJR-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxybiphenyls (CHEBI:17043 )
Insect repellents (C02499 )
a small molecule (CPD-946 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

fungicide

Biological Roles

Chemical Roles

environmental food contaminant

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	56°C
Boiling Point	Not Available
Solubility	0.7 mg/mL at 25°C
LogP	3.09

Predicted Properties

Property	Value	Source
Water Solubility	0.34 g/L	ALOGPS
logP	3.21	ALOGPS
logP	3.32	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.69	ChemAxon
pKa (Strongest Basic)	-5.6	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	53.18 m³·mol⁻¹	ChemAxon
Polarizability	18.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-1900000000-f58c83912c81582962ec	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00xr-1900000000-ba4f084280aee3b63cb9	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00xr-2900000000-0395543c94def63fbf1c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03fr-1790000000-2fec91e9a3b831e4f661	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-1900000000-f58c83912c81582962ec	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00xr-1900000000-ba4f084280aee3b63cb9	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00xr-2900000000-0395543c94def63fbf1c	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03fr-1790000000-2fec91e9a3b831e4f661	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0900000000-43bf1dee532a54447f41	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9760000000-5e1078b290b37f1d47bc	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0fml-0900000000-7b06dbf8c12560a092e6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0fb9-0900000000-dc2a630f122797c0a30d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udl-0900000000-0058244c148d04bcffb9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udl-0900000000-28f041bf0b0faf02ccd5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-00kf-9500000000-f6d4cbb6fefb881a66df	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00kf-9500000000-645cd80d916513b7da2e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0006-9200000000-cb0f070ccdf943ac78cc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0006-9200000000-e74e7ad70d8227b5a7e9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0fb9-0900000000-6327145722d77a345d12	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-0900000000-58d1482e199dc20e2e65	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0900000000-28311b68921ae494a0e8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0fb9-0900000000-931a5f59b51289796ad9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00dl-0900000000-85cbd30844e2c9d2b8cc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00kf-9600000000-6bdabf5fa4f9b4d076d0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00kf-9700000000-6e22867439b22f4327de	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0fb9-0900000000-c230f5371d3e1af25788	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0fb9-0900000000-665c01eb096b23432bf1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-aa09c65297232074b1da	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-042a540d9a28eba4bb1e	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f96-9600000000-ee2a147f3a7a3bbc0bda	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-05ec524c3078c379ec6f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900000000-cf114607f489ee954397	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9500000000-075a7f587e50b80d93c6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-13ac4e364e8d0c6b9e7c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-5e0bca337cd8a7eff74f	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01bc-3900000000-adae00e9be0477f3901b	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (16)

Uses/Sources

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

17043

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D3981.pdf

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
McDONOUGH ES: Inhibition of mold contamination in Drosophila food using sodium orthophenylphenate. Science. 1953 Oct 2;118(3066):388. [13101762 ]
Santhamma KR, Bhaduri A: Characterization of the respiratory chain of Leishmania donovani promastigotes. Mol Biochem Parasitol. 1995 Dec;75(1):43-53. [8720174 ]
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 ]
Ranzani MR, Fonseca H: Mycological evaluation of chemically-treated unshelled peanuts. Food Addit Contam. 1995 May-Jun;12(3):343-6. [7664925 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. 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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
Dissociation	2700 uM	Not Available	BindingDB 50308551

References

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

2. 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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.28 uM	NVS_GPCR_hPY2	Novascreen

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 ]

Target Details

3. 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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.24 uM	NVS_NR_hPPARa	Novascreen

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 ]

Target Details

4. 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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.44 uM	BSK_LPS_PGE2_down	BioSeek

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 ]

Target Details

5. 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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	8.65 uM	CLZD_CYP2B6_48	CellzDirect

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 ]

2-Biphenylol (T3D3981)

Structure for T3D3981: 2-Biphenylol

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References

Binding/Activity Constants

References