Galangin

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	6ec8aec2-2f26-49c8-9f67-70898f5c8655
Taxonomy	Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
IUPAC Name	3,5,7-trihydroxy-2-phenylchromen-4-one
SMILES (Canonical)	C1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O
SMILES (Isomeric)	C1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O
InChI	InChI=1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H
InChI Key	VCCRNZQBSJXYJD-UHFFFAOYSA-N
Popularity	1,359 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₅H₁₀O₅
Molecular Weight	270.24 g/mol
Exact Mass	270.05282342 g/mol
Topological Polar Surface Area (TPSA)	87.00 Å²
XlogP	2.30
Atomic LogP (AlogP)	2.58
H-Bond Acceptor	5
H-Bond Donor	3
Rotatable Bonds	1

Synonyms

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548-83-4

Norizalpinin

3,5,7-Trihydroxyflavone

3,5,7-Trihydroxy-2-phenyl-4H-chromen-4-one

3,5,7-triOH-Flavone

4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl-

3,5,7-Trihydroxy-2-phenyl-4-benzopyrone

3,5,7-trihydroxy-2-phenylchromen-4-one

FLAVONE, 3,5,7-TRIHYDROXY-

NSC-407229

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	+	0.9499	94.99%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6122	61.22%
OATP2B1 inhibitior	-	0.6673	66.73%
OATP1B1 inhibitior	+	0.8464	84.64%
OATP1B3 inhibitior	-	0.5697	56.97%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7046	70.46%
P-glycoprotein inhibitior	-	0.7356	73.56%
P-glycoprotein substrate	-	0.8544	85.44%
CYP3A4 substrate	-	0.5304	53.04%
CYP2C9 substrate	-	0.6443	64.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	+	0.7241	72.41%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.6434	64.34%
CYP2D6 inhibition	-	0.9083	90.83%
CYP1A2 inhibition	+	0.9108	91.08%
CYP2C8 inhibition	+	0.9221	92.21%
CYP inhibitory promiscuity	+	0.7652	76.52%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6985	69.85%
Eye corrosion	-	0.9903	99.03%
Eye irritation	+	0.9645	96.45%
Skin irritation	+	0.6294	62.94%
Skin corrosion	-	0.9563	95.63%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8713	87.13%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.7817	78.17%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7141	71.41%
Acute Oral Toxicity (c)	II	0.6238	62.38%
Estrogen receptor binding	+	0.9183	91.83%
Androgen receptor binding	+	0.8207	82.07%
Thyroid receptor binding	+	0.7095	70.95%
Glucocorticoid receptor binding	+	0.9156	91.56%
Aromatase binding	+	0.8891	88.91%
PPAR gamma	+	0.9367	93.67%
Honey bee toxicity	-	0.9177	91.77%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8967	89.67%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	12 nM	IC50	DOI: 10.1007/s00044-012-0353-y
CHEMBL251	P29274	Adenosine A2a receptor	16700 nM 18100 nM	Ki Ki	PMID: 9258366 PMID: 9258366
CHEMBL256	P0DMS8	Adenosine A3 receptor	3150 nM 3150 nM	Ki Ki	PMID: 8691424 PMID: 8576921
CHEMBL1914	P06276	Butyrylcholinesterase	6900 nM	Ki	PMID: 19879672
CHEMBL3729	P22748	Carbonic anhydrase IV	568.3 nM 568.3 nM	Ki Ki	via Super-PRED PMID: 26498393
CHEMBL2326	P43166	Carbonic anhydrase VII	24.5 nM 24.5 nM	Ki Ki	via Super-PRED PMID: 26498393
CHEMBL3242	O43570	Carbonic anhydrase XII	41.8 nM 41.8 nM	Ki Ki	PMID: 26498393 via Super-PRED
CHEMBL2231	P04798	Cytochrome P450 1A1	77 nM	IC50	PMID: 20696580
CHEMBL3356	P05177	Cytochrome P450 1A2	40 nM	IC50	PMID: 20696580
CHEMBL4878	Q16678	Cytochrome P450 1B1	25 nM 3 nM	IC50 IC50	PMID: 20696580 via Super-PRED
CHEMBL3622	P33261	Cytochrome P450 2C19	3981.1 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	3162.3 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	19952.6 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM 15848.9 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	11220.2 nM 17782.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1951	P21397	Monoamine oxidase A	130 nM	IC50	via Super-PRED
CHEMBL1929	P47989	Xanthine dehydrogenase	1800 nM	IC50	PMID: 9461655

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.25%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.10%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.06%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.75%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.42%	99.23%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.51%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.03%	99.15%
CHEMBL2424	Q04760	Glyoxalase I	85.75%	91.67%
CHEMBL3194	P02766	Transthyretin	85.67%	90.71%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	85.40%	95.72%
CHEMBL3401	O75469	Pregnane X receptor	84.99%	94.73%
CHEMBL1929	P47989	Xanthine dehydrogenase	84.93%	96.12%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.83%	94.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.37%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.34%	95.50%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.60%	93.99%

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.

Achyrocline flaccida

Adenostoma sparsifolium

Aglaia elaeagnoidea

Aldama linearis

Alnus alnobetula subsp. fruticosa