Trihydroxychalcone

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	0b325c7c-b3c0-4245-8a70-92218fd104b9
Taxonomy	Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > 2-Hydroxychalcones
IUPAC Name	(E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES (Canonical)	C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O
SMILES (Isomeric)	C1=CC(=CC=C1/C=C/C(=O)C2=C(C=C(C=C2)O)O)O
InChI	InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
InChI Key	DXDRHHKMWQZJHT-FPYGCLRLSA-N
Popularity	1,204 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₅H₁₂O₄
Molecular Weight	256.25 g/mol
Exact Mass	256.07355886 g/mol
Topological Polar Surface Area (TPSA)	77.80 Å²
XlogP	3.20
Atomic LogP (AlogP)	2.70
H-Bond Acceptor	4
H-Bond Donor	3
Rotatable Bonds	3

Synonyms

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961-29-5

2',4,4'-Trihydroxychalcone

(E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

4,2',4'-Trihydroxychalcone

6'-deoxychalcone

Isoliquiritigen

GU 17

2',4',4-Trihydroxychalcone

Chalcone, 2',4,4'-trihydroxy-

GU-17

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7711	77.11%
OATP2B1 inhibitior	-	0.7039	70.39%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9838	98.38%
BSEP inhibitior	-	0.6574	65.74%
P-glycoprotein inhibitior	-	0.9385	93.85%
P-glycoprotein substrate	-	0.9513	95.13%
CYP3A4 substrate	-	0.6718	67.18%
CYP2C9 substrate	-	0.6211	62.11%
CYP2D6 substrate	-	0.8534	85.34%
CYP3A4 inhibition	+	0.7959	79.59%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9350	93.50%
CYP2C8 inhibition	+	0.5638	56.38%
CYP inhibitory promiscuity	+	0.8559	85.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7472	74.72%
Carcinogenicity (trinary)	Non-required	0.7048	70.48%
Eye corrosion	-	0.9801	98.01%
Eye irritation	+	0.9919	99.19%
Skin irritation	+	0.6928	69.28%
Skin corrosion	-	0.9313	93.13%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8554	85.54%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.8967	89.67%
skin sensitisation	+	0.8772	87.72%
Respiratory toxicity	-	0.7444	74.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.6477	64.77%
Acute Oral Toxicity (c)	III	0.7921	79.21%
Estrogen receptor binding	+	0.9293	92.93%
Androgen receptor binding	+	0.8927	89.27%
Thyroid receptor binding	+	0.6737	67.37%
Glucocorticoid receptor binding	+	0.8590	85.90%
Aromatase binding	+	0.9380	93.80%
PPAR gamma	+	0.9077	90.77%
Honey bee toxicity	-	0.9037	90.37%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9906	99.06%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	via CMAUP
CHEMBL1900	P15121	Aldose reductase	320 nM 320 nM	IC50 IC50	via Super-PRED PMID: 22261024
CHEMBL2487	P05067	Beta amyloid A4 protein	19700 nM	IC50	PMID: 23786711
CHEMBL2179	P04062	Beta-glucocerebrosidase	11220.2 nM 4466.8 nM 19952.6 nM 11220.2 nM 3981.1 nM	Potency Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP
CHEMBL4822	P56817	Beta-secretase 1	33000 nM	IC50	DOI: 10.1007/s00044-012-0353-y
CHEMBL3622	P33261	Cytochrome P450 2C19	3981.1 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	7943.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	3981.1 nM 10000 nM 3981.1 nM 10000 nM	Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP
CHEMBL2789	P37059	Estradiol 17-beta-dehydrogenase 2	360 nM	IC50	via Super-PRED
CHEMBL242	Q92731	Estrogen receptor beta	269 nM	IC50	via Super-PRED
CHEMBL1293278	O75496	Geminin	15848.9 nM	Potency	via CMAUP
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	31622.8 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	251.2 nM	Potency	via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	11220.2 nM 11220.2 nM 10000 nM 7943.3 nM	Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	11600 nM	EC50	PMID: 25232969
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	31622.8 nM	Potency	via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	15101.4 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	12589.3 nM 6309.6 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	26121.6 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.99%	91.11%
CHEMBL3194	P02766	Transthyretin	95.74%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.11%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.29%	86.33%
CHEMBL1929	P47989	Xanthine dehydrogenase	86.52%	96.12%
CHEMBL4208	P20618	Proteasome component C5	84.79%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.31%	89.00%
CHEMBL2581	P07339	Cathepsin D	83.16%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.41%	91.71%
CHEMBL2535	P11166	Glucose transporter	81.12%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.84%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.48%	95.50%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Abies alba

Abies pinsapo subsp. marocana

Anemarrhena asphodeloides

Angelica acutiloba

Arnica mollis