8-(1,2-Dihydroxy-3-methylbut-3-enyl)chromen-2-one

Details

• Internal ID: c5c8ad67-e915-4a5b-a842-f72bc02e5ba0
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 8-(1,2-dihydroxy-3-methylbut-3-enyl)chromen-2-one
• SMILES (Canonical): CC(=C)C(C(C1=CC=CC2=C1OC(=O)C=C2)O)O
• SMILES (Isomeric): CC(=C)C(C(C1=CC=CC2=C1OC(=O)C=C2)O)O
• InChI: InChI=1S/C14H14O4/c1-8(2)12(16)13(17)10-5-3-4-9-6-7-11(15)18-14(9)10/h3-7,12-13,16-17H,1H2,2H3
• InChI Key: FIIAFNOOIKGYBV-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26 g/mol
• Exact Mass: 246.08920892 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9642	96.42%
Caco-2	-	0.6169	61.69%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5688	56.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9375	93.75%
OATP1B3 inhibitior	+	0.9798	97.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.6961	69.61%
P-glycoprotein inhibitior	-	0.8910	89.10%
P-glycoprotein substrate	-	0.8964	89.64%
CYP3A4 substrate	-	0.5687	56.87%
CYP2C9 substrate	-	0.8246	82.46%
CYP2D6 substrate	-	0.8416	84.16%
CYP3A4 inhibition	+	0.5747	57.47%
CYP2C9 inhibition	-	0.6996	69.96%
CYP2C19 inhibition	-	0.7091	70.91%
CYP2D6 inhibition	-	0.9277	92.77%
CYP1A2 inhibition	-	0.5082	50.82%
CYP2C8 inhibition	-	0.8894	88.94%
CYP inhibitory promiscuity	-	0.5776	57.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4977	49.77%
Eye corrosion	-	0.9763	97.63%
Eye irritation	-	0.6303	63.03%
Skin irritation	-	0.6056	60.56%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6674	66.74%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.5833	58.33%
skin sensitisation	-	0.6783	67.83%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.5607	56.07%
Acute Oral Toxicity (c)	III	0.5428	54.28%
Estrogen receptor binding	+	0.7658	76.58%
Androgen receptor binding	-	0.6420	64.20%
Thyroid receptor binding	+	0.6368	63.68%
Glucocorticoid receptor binding	+	0.5709	57.09%
Aromatase binding	+	0.8078	80.78%
PPAR gamma	+	0.7789	77.89%
Honey bee toxicity	-	0.8952	89.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9854	98.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.40%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.90%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.44%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.35%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.14%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.03%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.75%	91.11%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.74%	83.10%

Plants that contains it

• Micromelum minutum
• Murraya paniculata
• Rauia resinosa

Cross-Links

• PubChem: 5319844
• LOTUS: LTS0169293
• wikiData: Q104995718