OXYBENZONE

General Information

MaintermOXYBENZONE
CAS Reg.No.(or other ID)131-57-7
Regnum 177.1010

From www.fda.gov

Computed Descriptors

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2D Structure
CID4632
IUPAC Name(2-hydroxy-4-methoxyphenyl)-phenylmethanone
InChIInChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3
InChI KeyDXGLGDHPHMLXJC-UHFFFAOYSA-N
Canonical SMILESCOC1=CC(=C(C=C1)C(=O)C2=CC=CC=C2)O
Molecular FormulaC14H12O3
Wikipediaoxybenzone

From Pubchem

Computed Properties

Property Name Property Value
Molecular Weight228.247
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Complexity258.0
CACTVS Substructure Key Fingerprint A A A D c c B w M 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 I y B o A A B g C I A q B S A A A C C A A k I A A I i A E G C M g M J z a G N R q A c W A l 4 B U I u Y e I 7 O z O I A A A C A A I A A B A A A A Q A B A A A A A A A A A A A A = =
Topological Polar Surface Area46.5
Monoisotopic Mass228.079
Exact Mass228.079
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count17
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+0.8691
Human Intestinal AbsorptionHIA+0.9973
Caco-2 PermeabilityCaco2+0.9258
P-glycoprotein SubstrateNon-substrate0.6198
P-glycoprotein InhibitorNon-inhibitor0.7188
Non-inhibitor0.8124
Renal Organic Cation TransporterNon-inhibitor0.8178
Distribution
Subcellular localizationMitochondria0.9461
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7030
CYP450 2D6 SubstrateNon-substrate0.8915
CYP450 3A4 SubstrateNon-substrate0.6542
CYP450 1A2 InhibitorInhibitor0.9110
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9437
CYP450 2C19 InhibitorInhibitor0.8995
CYP450 3A4 InhibitorNon-inhibitor0.9258
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5000
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9358
Non-inhibitor0.9337
AMES ToxicityNon AMES toxic0.9098
CarcinogensNon-carcinogens0.8403
Fish ToxicityHigh FHMT0.9135
Tetrahymena Pyriformis ToxicityHigh TPT0.9927
Honey Bee ToxicityHigh HBT0.7696
BiodegradationNot ready biodegradable0.6452
Acute Oral ToxicityIV0.6369
Carcinogenicity (Three-class)Non-required0.5532

From admetSAR

ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-3.0669LogS
Caco-2 Permeability1.5484LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6986LD50, mol/kg
Fish Toxicity0.3535pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.3719pIGC50, ug/L

From admetSAR

Toxicity Profile

Route of ExposureNone
Mechanism of ToxicityOxybenzone absorbs UV-A ultraviolet rays, preventing them from reaching the skin.
MetabolismRoute of Elimination: In vivo studies show oxybenzone is abosorbed transdermally (through the skin) and is excreted in the urine.
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  1. Gonzalez H, Farbrot A, Larko O, Wennberg AM: Percutaneous absorption of the sunscreen benzophenone-3 after repeated whole-body applications, with and without ultraviolet irradiation. Br J Dermatol. 2006 Feb;154(2):337-40.[16433806 ]

From T3DB

Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzophenones
Intermediate Tree NodesNot available
Direct ParentBenzophenones
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzophenone - Diphenylmethane - Aryl-phenylketone - Methoxyphenol - Anisole - Phenoxy compound - Methoxybenzene - Benzoyl - Aryl ketone - Phenol ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Alkyl aryl ether - Vinylogous acid - Ketone - Ether - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

From ClassyFire

Targets

Target Details

Estrogen receptor

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
  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

Androgen receptor

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
  1. Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B: Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci. 2005 Feb;83(2):264-72. Epub 2004 Nov 10. [15537743 ]
Target Details

Estrogen receptor beta

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
  1. Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [16079615 ]
Target Details

Aromatase

General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 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

Progesterone receptor

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
  1. Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B: Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci. 2005 Feb;83(2):264-72. Epub 2004 Nov 10. [15537743 ]

From T3DB