Fraxetin

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	40f4e851-1cc1-4cb1-9219-54aed9f06248
Taxonomy	Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7,8-dihydroxycoumarins
IUPAC Name	7,8-dihydroxy-6-methoxychromen-2-one
SMILES (Canonical)	COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)O
SMILES (Isomeric)	COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)O
InChI	InChI=1S/C10H8O5/c1-14-6-4-5-2-3-7(11)15-10(5)9(13)8(6)12/h2-4,12-13H,1H3
InChI Key	HAVWRBANWNTOJX-UHFFFAOYSA-N
Popularity	266 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₀H₈O₅
Molecular Weight	208.17 g/mol
Exact Mass	208.03717335 g/mol
Topological Polar Surface Area (TPSA)	76.00 Å²
XlogP	1.20
Atomic LogP (AlogP)	1.21
H-Bond Acceptor	5
H-Bond Donor	2
Rotatable Bonds	1

Synonyms

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574-84-5

7,8-Dihydroxy-6-methoxycoumarin

7,8-Dihydroxy-6-methoxy-2H-chromen-2-one

7,8-dihydroxy-6-methoxychromen-2-one

2H-1-Benzopyran-2-one, 7,8-dihydroxy-6-methoxy-

UNII-CD3GD44O3K

7,8-Dihydroxy-6-methoxy-2-benzopyrone

CD3GD44O3K

7,8-Dihydroxy-6-methoxy-chromen-2-one

CHEMBL54909

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	+	0.9099	90.99%
Caco-2	-	0.7776	77.76%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7038	70.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9227	92.27%
OATP1B3 inhibitior	+	0.9900	99.00%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7915	79.15%
P-glycoprotein inhibitior	-	0.8967	89.67%
P-glycoprotein substrate	-	0.9488	94.88%
CYP3A4 substrate	-	0.6504	65.04%
CYP2C9 substrate	-	0.8321	83.21%
CYP2D6 substrate	-	0.8219	82.19%
CYP3A4 inhibition	-	0.8829	88.29%
CYP2C9 inhibition	-	0.9518	95.18%
CYP2C19 inhibition	-	0.8196	81.96%
CYP2D6 inhibition	-	0.9321	93.21%
CYP1A2 inhibition	+	0.9101	91.01%
CYP2C8 inhibition	-	0.6833	68.33%
CYP inhibitory promiscuity	-	0.7452	74.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5729	57.29%
Eye corrosion	-	0.9656	96.56%
Eye irritation	+	0.8999	89.99%
Skin irritation	-	0.5679	56.79%
Skin corrosion	-	0.9552	95.52%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8015	80.15%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.9199	91.99%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7761	77.61%
Acute Oral Toxicity (c)	III	0.6874	68.74%
Estrogen receptor binding	+	0.8844	88.44%
Androgen receptor binding	+	0.6475	64.75%
Thyroid receptor binding	-	0.7085	70.85%
Glucocorticoid receptor binding	+	0.8338	83.38%
Aromatase binding	+	0.6638	66.38%
PPAR gamma	+	0.6049	60.49%
Honey bee toxicity	-	0.9471	94.71%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5249	52.49%
Fish aquatic toxicity	+	0.9129	91.29%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM 25118.9 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	31622.8 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	12589.3 nM	Potency	via CMAUP
CHEMBL261	P00915	Carbonic anhydrase I	4860 nM	Ki	PMID: 22892213
CHEMBL3594	Q16790	Carbonic anhydrase IX	610 nM 610 nM	Ki Ki	PMID: 22892213 via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	4320 nM	Ki	PMID: 22892213
CHEMBL3242	O43570	Carbonic anhydrase XII	7700 nM	Ki	PMID: 22892213
CHEMBL3912	Q8N1Q1	Carbonic anhydrase XIII	9730 nM	Ki	PMID: 22892213
CHEMBL4801	P29466	Caspase-1	15848.9 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL3468	P55210	Caspase-7	19952.6 nM 15848.9 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	39810.7 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	25118.9 nM	Potency	via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	794.3 nM 1584.9 nM 794.3 nM	Potency Potency Potency	via Super-PRED via CMAUP via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	14125.4 nM 7079.5 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	15848.9 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM 14125.4 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	14125.4 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	14125.4 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	96.78%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.45%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.04%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.50%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.37%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.70%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.59%	99.23%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	83.16%	98.11%
CHEMBL3401	O75469	Pregnane X receptor	81.65%	94.73%
CHEMBL4208	P20618	Proteasome component C5	81.15%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.36%	99.17%

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.

Acer maximowiczianum

Aesculus hippocastanum

Ciliosemina pedunculata

Cleome viscosa

Frangula alnus

Fraxinus angustifolia subsp. oxycarpa

Fraxinus chinensis