5-Hydroxyseselin

Details

• Internal ID: dc0972b4-f91e-463b-a30f-659801bd6b3f
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Angular pyranocoumarins
• IUPAC Name: 5-hydroxy-8,8-dimethylpyrano[2,3-f]chromen-2-one
• SMILES (Canonical): CC1(C=CC2=C(O1)C=C(C3=C2OC(=O)C=C3)O)C
• SMILES (Isomeric): CC1(C=CC2=C(O1)C=C(C3=C2OC(=O)C=C3)O)C
• InChI: InChI=1S/C14H12O4/c1-14(2)6-5-9-11(18-14)7-10(15)8-3-4-12(16)17-13(8)9/h3-7,15H,1-2H3
• InChI Key: AFLYNAJQYYSXOS-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24 g/mol
• Exact Mass: 244.07355886 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 31525-75-4
• 5-hydroxy-8,8-dimethylpyrano[2,3-f]chromen-2-one
• 5-Hydroxy-8,8-dimethylpyrano[2,3-f]chromen-2(8H)-one
• CHEMBL448575
• HY-N10780
• AKOS040735085
• CS-0636027

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9882	98.82%
Caco-2	+	0.7621	76.21%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7700	77.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9237	92.37%
OATP1B3 inhibitior	+	0.9747	97.47%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6453	64.53%
P-glycoprotein inhibitior	-	0.7404	74.04%
P-glycoprotein substrate	-	0.7851	78.51%
CYP3A4 substrate	-	0.5154	51.54%
CYP2C9 substrate	-	0.6491	64.91%
CYP2D6 substrate	-	0.8338	83.38%
CYP3A4 inhibition	-	0.5852	58.52%
CYP2C9 inhibition	+	0.5343	53.43%
CYP2C19 inhibition	-	0.7147	71.47%
CYP2D6 inhibition	-	0.8574	85.74%
CYP1A2 inhibition	-	0.8149	81.49%
CYP2C8 inhibition	-	0.7650	76.50%
CYP inhibitory promiscuity	-	0.7501	75.01%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9713	97.13%
Carcinogenicity (trinary)	Non-required	0.5057	50.57%
Eye corrosion	-	0.9840	98.40%
Eye irritation	+	0.9200	92.00%
Skin irritation	-	0.6361	63.61%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6028	60.28%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	+	0.6158	61.58%
skin sensitisation	-	0.7274	72.74%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6524	65.24%
Acute Oral Toxicity (c)	III	0.5082	50.82%
Estrogen receptor binding	+	0.9712	97.12%
Androgen receptor binding	+	0.7561	75.61%
Thyroid receptor binding	+	0.6882	68.82%
Glucocorticoid receptor binding	+	0.9380	93.80%
Aromatase binding	+	0.8247	82.47%
PPAR gamma	+	0.7632	76.32%
Honey bee toxicity	-	0.9065	90.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9778	97.78%

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	99.05%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.57%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.33%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	91.43%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.24%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.74%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.50%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.39%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.40%	94.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	81.35%	85.30%
CHEMBL3401	O75469	Pregnane X receptor	81.29%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.84%	90.71%

Plants that contains it

• Citrus × aurantium
• Lysimachia arvensis
• Metrodorea flavida
• Uncaria perrottetii

Cross-Links

• PubChem: 11334023
• NPASS: NPC75528
• LOTUS: LTS0268636
• wikiData: Q105100425