8-Hydroxyartemidin

Details

• Internal ID: 6f82faa6-94e8-47ed-914a-51641b6423e5
• Taxonomy: Phenylpropanoids and polyketides > Isocoumarins and derivatives
• IUPAC Name: 3-[(E)-but-1-enyl]-8-hydroxyisochromen-1-one
• SMILES (Canonical): CCC=CC1=CC2=C(C(=CC=C2)O)C(=O)O1
• SMILES (Isomeric): CC/C=C/C1=CC2=C(C(=CC=C2)O)C(=O)O1
• InChI: InChI=1S/C13H12O3/c1-2-3-6-10-8-9-5-4-7-11(14)12(9)13(15)16-10/h3-8,14H,2H2,1H3/b6-3+
• InChI Key: KIVJBPPONQCANS-ZZXKWVIFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₃
• Molecular Weight: 216.23 g/mol
• Exact Mass: 216.078644241 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• CHEMBL446590
• (e)-(buten-1-yl)-8-hydroxyisocoumarin

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	+	0.9059	90.59%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Plasma membrane	0.5602	56.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8803	88.03%
OATP1B3 inhibitior	+	0.9846	98.46%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7653	76.53%
P-glycoprotein inhibitior	-	0.9067	90.67%
P-glycoprotein substrate	-	0.8963	89.63%
CYP3A4 substrate	-	0.5688	56.88%
CYP2C9 substrate	+	0.6673	66.73%
CYP2D6 substrate	-	0.8624	86.24%
CYP3A4 inhibition	-	0.8307	83.07%
CYP2C9 inhibition	-	0.7094	70.94%
CYP2C19 inhibition	-	0.5126	51.26%
CYP2D6 inhibition	-	0.9636	96.36%
CYP1A2 inhibition	+	0.7421	74.21%
CYP2C8 inhibition	-	0.6973	69.73%
CYP inhibitory promiscuity	-	0.5285	52.85%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9113	91.13%
Carcinogenicity (trinary)	Non-required	0.4193	41.93%
Eye corrosion	-	0.9454	94.54%
Eye irritation	+	0.9227	92.27%
Skin irritation	+	0.5369	53.69%
Skin corrosion	-	0.9540	95.40%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7320	73.20%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.6678	66.78%
skin sensitisation	-	0.6901	69.01%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.5660	56.60%
Acute Oral Toxicity (c)	III	0.5960	59.60%
Estrogen receptor binding	+	0.8921	89.21%
Androgen receptor binding	+	0.6613	66.13%
Thyroid receptor binding	+	0.5663	56.63%
Glucocorticoid receptor binding	+	0.7694	76.94%
Aromatase binding	+	0.8565	85.65%
PPAR gamma	+	0.8806	88.06%
Honey bee toxicity	-	0.9680	96.80%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9596	95.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.07%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.21%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.50%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	94.10%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.35%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.23%	94.00%
CHEMBL3959	P16083	Quinone reductase 2	85.76%	89.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.13%	93.99%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.48%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.16%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.90%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	82.65%	91.49%

Plants that contains it

• Artemisia dracunculus

Cross-Links

• PubChem: 44575586
• NPASS: NPC91475