Artemidinol

Details

• Internal ID: c75be640-a4f5-45dc-a5e5-38d30c7cfd03
• Taxonomy: Phenylpropanoids and polyketides > Isocoumarins and derivatives
• IUPAC Name: 3-[(E)-but-1-enyl]-5-hydroxyisochromen-1-one
• SMILES (Canonical): CCC=CC1=CC2=C(C=CC=C2O)C(=O)O1
• SMILES (Isomeric): CC/C=C/C1=CC2=C(C=CC=C2O)C(=O)O1
• InChI: InChI=1S/C13H12O3/c1-2-3-5-9-8-11-10(13(15)16-9)6-4-7-12(11)14/h3-8,14H,2H2,1H3/b5-3+
• InChI Key: QBZHMYUXUVZDQT-HWKANZROSA-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: 3.00
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 62268-43-3
• CHEMBL471176
• CHEBI:174091
• DTXSID401223415
• (e)-3-(buten-1-yl)-5-hydroxyisocoumarin
• 3-[(E)-but-1-enyl]-5-hydroxyisochromen-1-one
• 3-(1-Butenyl)-5-hydroxy-1H-2-benzopyran-1-one
• 3-(1E)-1-Buten-1-yl-5-hydroxy-1H-2-benzopyran-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.7556	75.56%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Plasma membrane	0.4891	48.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8872	88.72%
OATP1B3 inhibitior	+	0.9739	97.39%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8358	83.58%
P-glycoprotein inhibitior	-	0.8228	82.28%
P-glycoprotein substrate	-	0.8768	87.68%
CYP3A4 substrate	-	0.5542	55.42%
CYP2C9 substrate	-	0.5603	56.03%
CYP2D6 substrate	-	0.8489	84.89%
CYP3A4 inhibition	-	0.8429	84.29%
CYP2C9 inhibition	-	0.5431	54.31%
CYP2C19 inhibition	-	0.6307	63.07%
CYP2D6 inhibition	-	0.9624	96.24%
CYP1A2 inhibition	+	0.6625	66.25%
CYP2C8 inhibition	-	0.7089	70.89%
CYP inhibitory promiscuity	-	0.5778	57.78%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8913	89.13%
Carcinogenicity (trinary)	Non-required	0.4229	42.29%
Eye corrosion	-	0.9614	96.14%
Eye irritation	+	0.9371	93.71%
Skin irritation	-	0.5119	51.19%
Skin corrosion	-	0.9583	95.83%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7916	79.16%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.6107	61.07%
skin sensitisation	-	0.6536	65.36%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8778	87.78%
Acute Oral Toxicity (c)	III	0.7105	71.05%
Estrogen receptor binding	+	0.7431	74.31%
Androgen receptor binding	+	0.7705	77.05%
Thyroid receptor binding	+	0.5532	55.32%
Glucocorticoid receptor binding	+	0.8276	82.76%
Aromatase binding	+	0.7089	70.89%
PPAR gamma	+	0.8193	81.93%
Honey bee toxicity	-	0.9673	96.73%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9647	96.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.91%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.83%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.90%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.76%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.43%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.86%	93.99%
CHEMBL1951	P21397	Monoamine oxidase A	86.16%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.51%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.90%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.77%	94.00%

Plants that contains it

• Artemisia dracunculus

Cross-Links

• PubChem: 23264915
• NPASS: NPC46634