Pyrogallol

Details

• Internal ID: 68bf4f65-e6b1-48cb-acae-9bb8580d3360
• Taxonomy: Benzenoids > Phenols > Benzenetriols and derivatives > Pyrogallols and derivatives > 5-unsubstituted pyrrogallols
• IUPAC Name: benzene-1,2,3-triol
• SMILES (Canonical): C1=CC(=C(C(=C1)O)O)O
• SMILES (Isomeric): C1=CC(=C(C(=C1)O)O)O
• InChI: InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
• InChI Key: WQGWDDDVZFFDIG-UHFFFAOYSA-N
• Popularity: 9,870 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₆O₃
• Molecular Weight: 126.11 g/mol
• Exact Mass: 126.031694049 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• benzene-1,2,3-triol
• 87-66-1
• 1,2,3-trihydroxybenzene
• pyrogallic acid
• 1,2,3-benzenetriol
• fourrine PG
• Fouramine Brown AP
• fourrine 85
• Pyro
• Piral
• C.I. Oxidation Base 32
• fouramine base ap
• Benzenetriol
• C.I. 76515
• 1,2,3-Trihydroxybenzen
• CI Oxidation Base 32
• Benzene, 1,2,3-trihydroxy-
• NSC 5035
• 2,3-Dihydroxyphenol
• CCRIS 1940
• HSDB 794
• NSC-5035
• Pyrogallol [NF]
• EINECS 201-762-9
• UNII-01Y4A2QXY0
• BRN 0907431
• 01Y4A2QXY0
• Pyrogallol [NF X]
• CI 76515
• DTXSID6025983
• CHEBI:16164
• AI3-00709
• 1,2,3-Trihydroxybenzen [Czech]
• 1,2,3-TRIHYDROXY-BENZENE
• benzene-1,2-3-triol
• CHEMBL307145
• DTXCID905983
• 35296-77-6
• 4-06-00-07327 (Beilstein Handbook Reference)
• Benzene-1,2,3-triol (Pyrogallol)
• MFCD00002192
• NCGC00091507-01
• 1, 2, 3-Benzenetriol
• PYROGALLOL (MART.)
• PYROGALLOL [MART.]
• 1,2,3-Trihydroxybenzen (CZECH)
• acid, Pyrogallic
• CAS-87-66-1
• PYG
• PYROGALLOL, ACS
• Pirogalol
• Pyrogallol acid
• Pyrogallol;
• trihydroxybenzene
• 1,3-Benzenetriol
• Pyrogallol, 98%
• Pyrogallol (8CI)
• 2,3-Dihidroxifenol
• PYROP
• 2 3-Dihydroxyphenol
• 2 6-Dihydroxyphenol
• Pyrogallol ACS grade
• 1,3-Trihydroxybenzen
• Pyrogallic Acid,(S)
• 1,2,3-bencenotriol
• 1,3-Trihydroxybenzene
• 123-Trihydroxybenzene
• PGA (CHRIS Code)
• benceno-1,2,3-triol
• PYROGALLOL [MI]
• Benzene-1 2 3-triol
• Pyrogallol, ACS reagent
• 1,2,3-trihidroxibenceno
• PYROGALLOL [HSDB]
• PYROGALLOL [INCI]
• Benzene,2,3-trihydroxy-
• WLN: QR BQ CQ
• PYROGALLOL [VANDF]
• D06TPF
• SCHEMBL3532
• PYROGALLOL [WHO-DD]
• C.I. Oxidation Base 32
• MLS001066376
• Pyrogallol, analytical standard
• 1,2,3-Trihydroxybenzene, XIV
• Pyrogallol, >=98% (HPLC)
• Pyrogallol, p.a., ACS reagent
• NSC5035
• BCP15871
• HY-N1579
• Pyrogallol, ACS reagent, >=99%
• STR08708
• Tox21_111143
• Tox21_202373
• BBL011607
• BDBM50031472
• Pyrogallol, Vetec(TM) reagent grade
• s3885
• STL163335
• Pyrogallol: C.I. Oxidation base 32
• AKOS000120163
• AM10660
• CCG-266100
• CS-W019928
• LS-1870
• 2,2',2"-[1,2,3-BENZENE-TRIYLTRIS(OXY)]TRIS[N,N,N-TRIETHYLETHANAMINIUM]
• 1,2,3-Benzenetriol (ACD/Name 4.0)
• NCGC00091507-02
• NCGC00091507-03
• NCGC00259922-01
• Pyrogallol, purum, >=98.0% (HPLC)
• AC-11384
• BP-12538
• GMN
• Pyrogallol, SAJ first grade, >=98.0%
• SMR000471842
• Pyrogallol, JIS special grade, >=99.0%
• FT-0606230
• P0570
• EN300-18055
• C01108
• AB-131/40221933
• Q388692
• W-104009
• Z57127553
• 2,3-Dihydroxyphenol; Benzene-1,2,3-triol; NSC 5035
• F0001-2163
• InChI=1/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9
• 30813-84-4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9581	95.81%
Caco-2	+	0.7022	70.22%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6807	68.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9560	95.60%
OATP1B3 inhibitior	+	0.9810	98.10%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9692	96.92%
P-glycoprotein inhibitior	-	0.9857	98.57%
P-glycoprotein substrate	-	0.9884	98.84%
CYP3A4 substrate	-	0.8128	81.28%
CYP2C9 substrate	-	0.6786	67.86%
CYP2D6 substrate	-	0.7035	70.35%
CYP3A4 inhibition	-	0.8682	86.82%
CYP2C9 inhibition	-	0.8271	82.71%
CYP2C19 inhibition	-	0.9397	93.97%
CYP2D6 inhibition	-	0.9494	94.94%
CYP1A2 inhibition	-	0.7436	74.36%
CYP2C8 inhibition	-	0.9345	93.45%
CYP inhibitory promiscuity	-	0.6899	68.99%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7823	78.23%
Carcinogenicity (trinary)	Non-required	0.5339	53.39%
Eye corrosion	+	0.7596	75.96%
Eye irritation	+	0.9943	99.43%
Skin irritation	+	0.9253	92.53%
Skin corrosion	+	0.8231	82.31%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8206	82.06%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.9250	92.50%
skin sensitisation	+	0.9772	97.72%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.7245	72.45%
Acute Oral Toxicity (c)	III	0.8089	80.89%
Estrogen receptor binding	-	0.6191	61.91%
Androgen receptor binding	-	0.6671	66.71%
Thyroid receptor binding	-	0.6969	69.69%
Glucocorticoid receptor binding	-	0.7776	77.76%
Aromatase binding	-	0.8782	87.82%
PPAR gamma	-	0.7015	70.15%
Honey bee toxicity	-	0.9872	98.72%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.7880	78.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	10000 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	1498.9 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	12589.3 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	6309.6 nM	Potency	via CMAUP
CHEMBL261	P00915	Carbonic anhydrase I	7410 nM	Ki	PMID: 21669522
CHEMBL205	P00918	Carbonic anhydrase II	540 nM; 540 nM	Ki; Ki	PMID: 21669522; via Super-PRED
CHEMBL3025	P23280	Carbonic anhydrase VI	520 nM; 520 nM	Ki; Ki	via Super-PRED; PMID: 21669522
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	631 nM; 631 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	1230 nM	IC50	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	14125.4 nM	Potency	via CMAUP
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	997 nM	IC50	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	86.5 nM; 86.5 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.71%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	90.47%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.37%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.16%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.62%	99.15%

Plants that contains it

• Acacia confusa
• Agave americana
• Bixa orellana
• Brassica oleracea
• Crocus sativus
• Erica arborea
• Erica arborea
• Eucommia ulmoides
• Euphorbia hirta
• Euphorbia tithymaloides
• Geranium thunbergii
• Gunnera perpensa
• Hamamelis virginiana
• Isodon lihsienensis
• Orostachys fimbriata
• Peperomia heyneana
• Persicaria bistorta
• Phoebe clemensii
• Phyllanthus emblica
• Populus deltoides
• Posidonia oceanica
• Quercus robur
• Reynoutria multiflora
• Rhodiola crenulata
• Rhododendron mucronatum
• Rubia cordifolia
• Rubus rigidus
• Rumex chalepensis
• Rumex japonicus
• Saxifraga stolonifera
• Terminalia chebula

Cross-Links

• PubChem: 1057
• NPASS: NPC280254
• ChEMBL: CHEMBL307145
• LOTUS: LTS0062059
• wikiData: Q388692