Phloroglucinol

Details

• Internal ID: d9c1d5c6-df1a-42c7-b0e3-86d4764c7006
• Taxonomy: Benzenoids > Phenols > Benzenetriols and derivatives > Phloroglucinols and derivatives
• IUPAC Name: benzene-1,3,5-triol
• SMILES (Canonical): C1=C(C=C(C=C1O)O)O
• SMILES (Isomeric): C1=C(C=C(C=C1O)O)O
• InChI: InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
• InChI Key: QCDYQQDYXPDABM-UHFFFAOYSA-N
• Popularity: 7,468 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: 0.20
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 108-73-6
• Benzene-1,3,5-triol
• 1,3,5-benzenetriol
• 1,3,5-trihydroxybenzene
• Phloroglucin
• Phloroglucine
• Spasfon-Lyoc
• Dilospan S
• sym-Trihydroxybenzene
• s-Trihydroxybenzene
• Benzene, trihydroxy
• Floroglucin
• Floroglucinol
• DHD7FFG6YS
• Benezene-1,3,5-triol
• NSC-1572
• DTXSID9048354
• CHEBI:16204
• RefChem:6129
• DTXCID0028329
• 203-611-2
• Benzene-s-triol
• Phloroglucinol anhydrous
• 3,5-Dihydroxyphenol
• 5-Hydroxyresorcinol
• 5-Oxyresorcinol
• 5-Oxyresorcinolphloroglucin
• MFCD00002286
• 1,3,5-THB
• Phloroglucinol, anhydrous
• 1,3,5-Trihydroxycyclohexatriene
• 1,3,5-Triol
• Benzene, 1,3,5-trihydroxy-
• 5-Benzenetriol
• NSC 1572
• Phloroglucinol (JAN)
• CHEMBL473159
• PHLOROGLUCINOL [JAN]
• Floroglucin [Czech]
• Floroglucinol [Czech]
• CCRIS 4147
• UNII-DHD7FFG6YS
• NCGC00166270-01
• 1,2,5-trihydroxybenzene
• EINECS 203-611-2
• BRN 1341907
• AI3-08848
• 1,5-Benzenetriol
• 13X
• Dilospan S (TN)
• Phloroglucinol [BAN]
• 1,5-Trihydroxybenzene
• 1,5-Triol
• Benzene,3,5-trihydroxy-
• Phloroglucinol (anhydrous)
• WLN: QR CQ EQ
• 1,3,5-trihydroxylbenzene
• 1,3,5-trihydroxy-benzene
• PHLOROGLUCINOL [MI]
• 1,3, 5-Trihydroxybenzene
• SCHEMBL26311
• SCHEMBL82570
• 1,5-Trihydroxycyclohexatriene
• 4-06-00-07361 (Beilstein Handbook Reference)
• Phloroglucinol, p.a., 99%
• PHLOROGLUCINOL [MART.]
• SCHEMBL3711657
• PHLOROGLUCINOL [WHO-DD]
• 1,3,5-Benzenetriol, anhydrous
• SCHEMBL30710583
• NSC1572
• EDC49724
• BBL018701
• BDBM50249069
• CS0115
• MSK168374
• PHLOROGLUCINOL [EP MONOGRAPH]
• STL146346
• phloroglucinol (1,3,5-benzenetriol)
• Phloroglucinol, >=99.0% (HPLC)
• AKOS000119851
• DB12944
• FP12341
• FS-4574
• 1,3,5-Benzenetriol (ACD/Name 4.0)
• NCGC00166270-02
• AC-10081
• NS00013979
• P0249
• P1376
• ST50214381
• EN300-19648
• Phloroglucinol 100 microg/mL in Acetonitrile
• C02183
• D00152
• F13526
• SBI-0653926.0001
• A801919
• Q899008
• BRD-K00405906-001-01-9
• Phloroglucinol, plant cell culture tested, BioReagent
• F0001-0177
• Z104474594
• Phloroglucinol, Used to detect the presence of wood fiber.
• 1,3,5-Benzenetriol; 1,3,5-THB; 1,3,5-Trihydroxybenzene
• InChI=1/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9
• Phloroglucinol (anhydrous), European Pharmacopoeia (EP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9799	97.99%
Caco-2	+	0.8470	84.70%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7706	77.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9478	94.78%
OATP1B3 inhibitior	+	0.9728	97.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9508	95.08%
P-glycoprotein inhibitior	-	0.9835	98.35%
P-glycoprotein substrate	-	0.9958	99.58%
CYP3A4 substrate	-	0.8585	85.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6676	66.76%
CYP3A4 inhibition	-	0.5353	53.53%
CYP2C9 inhibition	-	0.7638	76.38%
CYP2C19 inhibition	-	0.6454	64.54%
CYP2D6 inhibition	-	0.9542	95.42%
CYP1A2 inhibition	-	0.6191	61.91%
CYP2C8 inhibition	-	0.9571	95.71%
CYP inhibitory promiscuity	-	0.6500	65.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6787	67.87%
Carcinogenicity (trinary)	Non-required	0.6557	65.57%
Eye corrosion	+	0.7480	74.80%
Eye irritation	+	0.9921	99.21%
Skin irritation	+	0.9245	92.45%
Skin corrosion	+	0.6173	61.73%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7478	74.78%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	+	0.8833	88.33%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	+	0.5631	56.31%
Acute Oral Toxicity (c)	III	0.8100	81.00%
Estrogen receptor binding	-	0.8174	81.74%
Androgen receptor binding	-	0.8078	80.78%
Thyroid receptor binding	-	0.7158	71.58%
Glucocorticoid receptor binding	-	0.8858	88.58%
Aromatase binding	-	0.8506	85.06%
PPAR gamma	-	0.7020	70.20%
Honey bee toxicity	-	0.9672	96.72%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.3924	39.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4822	P56817	Beta-secretase 1	36470 nM	IC50	PMID: 20462757

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.74%	91.11%

Plants that contains it

• Achillea millefolium
• Alkanna cappadocica
• Allium cepa
• Alpinia roxburghii
• Artemisia dolosa
• Artemisia rupestris subsp. rupestris
• Atalantia racemosa
• Buddleja cordata
• Cannabis sativa
• Cornus capitata
• Crambe tataria
• Diospyros eriantha
• Drimia sanguinea
• Dryopteris crassirhizoma
• Fritillaria monantha
• Haematoxylum brasiletto
• Hoffmannia strigillosa
• Humulus lupulus
• Hypericum perforatum
• Millettia erythrocalyx
• Myrsine lancifolia
• Ononis vaginalis
• Pluchea lanceolata
• Posidonia oceanica
• Pteris semipinnata
• Salvia hispanica
• Sorghum halepense
• Spatholobus suberectus
• Stenocereus griseus
• Syncarpia hillii
• Takhtajaniantha pseudodivaricata
• Vachellia nilotica subsp. tomentosa

Cross-Links

• PubChem: 359
• NPASS: NPC4154
• ChEMBL: CHEMBL473159
• LOTUS: LTS0267010
• wikiData: Q899008