General Information

Chemical nameBenzene-1,2-diol
CAS number120-80-9
COE number680
Flavouring typesubstances
FL No.04.029
MixtureNo
Purity of the named substance at least 95% unless otherwise specified

From webgate.ec.europa.eu

Computed Descriptors

Download SDF
2D Structure
CID289
IUPAC Namebenzene-1,2-diol
InChIInChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
InChI KeyYCIMNLLNPGFGHC-UHFFFAOYSA-N
Canonical SMILESC1=CC=C(C(=C1)O)O
Molecular FormulaC6H6O2
Wikipediapyrocatechol

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight110.112
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Complexity62.9
CACTVS Substructure Key Fingerprint A A A D c Y B g 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 A A A A A A A A A A A B A A A A G g A A C A A A C A S A k A A w B o A A A g C A A C B C A A A C A A A g I A A I i A A G i I g J J i K C E R K A c A E k w B E J m A e A Q A A A A A A A A A A A Q A A A A A A A A A C A A A A A A A A A A A = =
Topological Polar Surface Area40.5
Monoisotopic Mass110.037
Exact Mass110.037
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count8
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+0.5000
Human Intestinal AbsorptionHIA+0.9782
Caco-2 PermeabilityCaco2+0.8824
P-glycoprotein SubstrateNon-substrate0.7207
P-glycoprotein InhibitorNon-inhibitor0.9705
Non-inhibitor0.9926
Renal Organic Cation TransporterNon-inhibitor0.9134
Distribution
Subcellular localizationMitochondria0.8082
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8247
CYP450 2D6 SubstrateNon-substrate0.8574
CYP450 3A4 SubstrateNon-substrate0.7305
CYP450 1A2 InhibitorNon-inhibitor0.8949
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9579
CYP450 2C19 InhibitorNon-inhibitor0.9348
CYP450 3A4 InhibitorNon-inhibitor0.9570
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7461
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9322
Non-inhibitor0.8953
AMES ToxicityNon AMES toxic0.6674
CarcinogensNon-carcinogens0.8689
Fish ToxicityHigh FHMT0.7424
Tetrahymena Pyriformis ToxicityHigh TPT0.9702
Honey Bee ToxicityHigh HBT0.6926
BiodegradationReady biodegradable0.6877
Acute Oral ToxicityII0.7741
Carcinogenicity (Three-class)Warning0.5621

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-0.0276LogS
Caco-2 Permeability1.1463LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5957LD50, mol/kg
Fish Toxicity1.0318pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6327pIGC50, ug/L

From admetSAR


Toxicity Profile

Route of ExposureNone
Mechanism of ToxicityNone
MetabolismNone
Toxicity ValuesNone
Lethal DoseNone
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans.
Minimum Risk LevelNone
Health EffectsNone
TreatmentNone
Reference
  1. Nguyen SD, Sok DE: Effect of 3,4-dihydroxyphenylalanine on Cu(2+)-induced inactivation of HDL-associated paraoxonasel and oxidation of HDL; inactivation of paraoxonasel activity independent of HDL lipid oxidation. Free Radic Res. 2004 Sep;38(9):969-76.[15621715 ]
  2. Kiso Y: Antioxidative roles of sesamin, a functional lignan in sesame seed, and it's effect on lipid- and alcohol-metabolism in the liver: a DNA microarray study. Biofactors. 2004;21(1-4):191-6.[15630196 ]
  3. Rivest J, Barclay CL, Suchowersky O: COMT inhibitors in Parkinson's disease. Can J Neurol Sci. 1999 Aug;26 Suppl 2:S34-8.[10451758 ]
  4. Goodall M, Diddle AW: Epinephrine and norepinephrine in pregnancy. A comparative study of the adrenal gland and catechol output in different species of animals and man. Am J Obstet Gynecol. 1971 Dec 1;111(7):896-904.[5118028 ]
  5. Olanow CW, Obeso JA: Pulsatile stimulation of dopamine receptors and levodopa-induced motor complications in Parkinson's disease: implications for the early use of COMT inhibitors. Neurology. 2000;55(11 Suppl 4):S72-7; discussion S78-81.[11147513 ]
  6. Zand R, Nelson SD, Slattery JT, Thummel KE, Kalhorn TF, Adams SP, Wright JM: Inhibition and induction of cytochrome P4502E1-catalyzed oxidation by isoniazid in humans. Clin Pharmacol Ther. 1993 Aug;54(2):142-9.[8354023 ]
  7. Swaminath G, Deupi X, Lee TW, Zhu W, Thian FS, Kobilka TS, Kobilka B: Probing the beta2 adrenoceptor binding site with catechol reveals differences in binding and activation by agonists and partial agonists. J Biol Chem. 2005 Jun 10;280(23):22165-71. Epub 2005 Apr 7.[15817484 ]
  8. Habecker BA, Willison BD, Shi X, Woodward WR: Chronic depolarization stimulates norepinephrine transporter expression via catecholamines. J Neurochem. 2006 May;97(4):1044-51. Epub 2006 Mar 29.[16573647 ]
  9. Goldstein DS, Holmes C, Kaufmann H, Freeman R: Clinical pharmacokinetics of the norepinephrine precursor L-threo-DOPS in primary chronic autonomic failure. Clin Auton Res. 2004 Dec;14(6):363-8.[15666063 ]
  10. Schapira AH, Obeso JA, Olanow CW: The place of COMT inhibitors in the armamentarium of drugs for the treatment of Parkinson's disease. Neurology. 2000;55(11 Suppl 4):S65-8; discussion S69-71.[11147512 ]
  11. Purba HS, Maggs JL, Orme ML, Back DJ, Park BK: The metabolism of 17 alpha-ethinyloestradiol by human liver microsomes: formation of catechol and chemically reactive metabolites. Br J Clin Pharmacol. 1987 Apr;23(4):447-53.[3555579 ]
  12. Moretti M, Villarini M, Simonucci S, Fatigoni C, Scassellati-Sforzolini G, Monarca S, Pasquini R, Angelucci M, Strappini M: Effects of co-exposure to extremely low frequency (ELF) magnetic fields and benzene or benzene metabolites determined in vitro by the alkaline comet assay. Toxicol Lett. 2005 Jun 17;157(2):119-28.[15836999 ]
  13. Poupaert J, Carato P, Colacino E, Yous S: 2(3H)-benzoxazolone and bioisosters as "privileged scaffold" in the design of pharmacological probes. Curr Med Chem. 2005;12(7):877-85.[15853716 ]
  14. Mosca L, Lendaro E, d'Erme M, Marcellini S, Moretti S, Rosei MA: 5-S-Cysteinyl-dopamine effect on the human dopaminergic neuroblastoma cell line SH-SY5Y. Neurochem Int. 2006 Aug;49(3):262-9. Epub 2006 Mar 20.[16549224 ]
  15. Santens P: Sleep attacks in Parkinson's disease induced by Entacapone, a COMT-inhibitor. Fundam Clin Pharmacol. 2003 Feb;17(1):121-3.[12588639 ]
  16. Cavalieri EL, Rogan EG, Chakravarti D: Initiation of cancer and other diseases by catechol ortho-quinones: a unifying mechanism. Cell Mol Life Sci. 2002 Apr;59(4):665-81.[12022473 ]
  17. Relling MV, Nemec J, Schuetz EG, Schuetz JD, Gonzalez FJ, Korzekwa KR: O-demethylation of epipodophyllotoxins is catalyzed by human cytochrome P450 3A4. Mol Pharmacol. 1994 Feb;45(2):352-8.[8114683 ]
  18. Irons RD: Quinones as toxic metabolites of benzene. J Toxicol Environ Health. 1985;16(5):673-8.[4093989 ]
  19. Luffer-Atlas D, Vincent SH, Painter SK, Arison BH, Stearns RA, Chiu SH: Orally active inhibitors of human leukocyte elastase. III. Identification and characterization of metabolites of L-694,458 by liquid chromatography-tandem mass spectrometry. Drug Metab Dispos. 1997 Aug;25(8):940-52.[9280402 ]
  20. Munns AJ, De Voss JJ, Hooper WD, Dickinson RG, Gillam EM: Bioactivation of phenytoin by human cytochrome P450: characterization of the mechanism and targets of covalent adduct formation. Chem Res Toxicol. 1997 Sep;10(9):1049-58.[9305589 ]

From T3DB


Taxonomic Classification

KingdomOrganic compounds
SuperclassBenzenoids
ClassPhenols
SubclassBenzenediols
Intermediate Tree NodesNot available
Direct ParentCatechols
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsCatechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Monocyclic benzene moiety - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as catechols. These are compounds containing a 1,2-benzenediol moiety.

From ClassyFire


Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Key regulator of cellular differentiation, immunity, peripheral circadian rhythm as well as lipid, steroid, xenobiotics and glucose metabolism. Considered to have intrinsic transcriptional activity, have some natural ligands like oxysterols that act as agonists (25-hydroxycholesterol) or inverse agonists (7-oxygenated sterols), enhancing or repressing the transcriptional activity, respectively. Recruits distinct combinations of cofactors to target gene regulatory regions to modulate their transcriptional expression, depending on the tissue, time and promoter contexts. Regulates the circadian expression of clock genes such as CRY1, ARNTL/BMAL1 and NR1D1 in peripheral tissues and in a tissue-selective manner. Competes with NR1D1 for binding to their shared DNA response element on some clock genes such as ARNTL/BMAL1, CRY1 and NR1D1 itself, resulting in NR1D1-mediated repression or RORC-mediated activation of the expression, leading to the circadian pattern of clock genes expression. Therefore influences the period length and stability of the clock. Involved in the regulation of the rhythmic expression of genes involved in glucose and lipid metabolism, including PLIN2 and AVPR1A. Negative regulator of adipocyte differentiation through the regulation of early phase genes expression, such as MMP3. Controls adipogenesis as well as adipocyte size and modulates insulin sensitivity in obesity. In liver, has specific and redundant functions with RORA as positive or negative modulator of expression of genes encoding phase I and Phase II proteins involved in the metabolism of lipids, steroids and xenobiotics, such as SULT1E1. Also plays also a role in the regulation of hepatocyte glucose metabolism through the regulation of G6PC and PCK1. Regulates the rhythmic expression of PROX1 and promotes its nuclear localization (By similarity). Plays an indispensable role in the induction of IFN-gamma dependent anti-mycobacterial systemic immunity (PubMed:26160376).Isoform 2: Essential for thymopoiesis and the development of several secondary lymphoid tissues, including lymph nodes and Peyer's patches. Required for the generation of LTi (lymphoid tissue inducer) cells. Regulates thymocyte survival through DNA-binding on ROREs of target gene promoter regions and recruitment of coactivaros via the AF-2. Also plays a key role, downstream of IL6 and TGFB and synergistically with RORA, for lineage specification of uncommitted CD4(+) T-helper (T(H)) cells into T(H)17 cells, antagonizing the T(H)1 program. Probably regulates IL17 and IL17F expression on T(H) by binding to the essential enhancer conserved non-coding sequence 2 (CNS2) in the IL17-IL17F locus. May also play a role in the pre-TCR activation cascade leading to the maturation of alpha/beta T-cells and may participate in the regulation of DNA accessibility in the TCR-J(alpha) locus.
Gene Name:
RORC
Uniprot ID:
P51449
Molecular Weight:
58194.845 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 ]
General Function:
Ferric iron binding
Gene Name:
catA
Uniprot ID:
P07773
Molecular Weight:
34347.02 Da
General Function:
Ferrous iron binding
Specific Function:
Shows a preference for catechols with groups immediately adjacent to the hydroxyl substituents.
Gene Name:
bphC
Uniprot ID:
P47228
Molecular Weight:
32470.515 Da

From T3DB