7-hydroxy-8-[(E)-4-hydroxy-3-methylbut-2-enyl]chromen-2-one

Details

• Internal ID: a43bd7ce-a251-4f87-b999-71e7cb080fe8
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 7-hydroxy-8-[(E)-4-hydroxy-3-methylbut-2-enyl]chromen-2-one
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1OC(=O)C=C2)O)CO
• SMILES (Isomeric): C/C(=C\CC1=C(C=CC2=C1OC(=O)C=C2)O)/CO
• InChI: InChI=1S/C14H14O4/c1-9(8-15)2-5-11-12(16)6-3-10-4-7-13(17)18-14(10)11/h2-4,6-7,15-16H,5,8H2,1H3/b9-2+
• InChI Key: TXAQUMCUNALGRP-XNWCZRBMSA-N
• Popularity: 1 reference 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: 2.20
• Atomic LogP (AlogP): 1.98
• 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	+	0.9797	97.97%
Caco-2	-	0.5472	54.72%
Blood Brain Barrier	-	0.7072	70.72%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7456	74.56%
OATP2B1 inhibitior	-	0.7178	71.78%
OATP1B1 inhibitior	+	0.8896	88.96%
OATP1B3 inhibitior	+	0.9548	95.48%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6560	65.60%
P-glycoprotein inhibitior	-	0.9291	92.91%
P-glycoprotein substrate	-	0.9239	92.39%
CYP3A4 substrate	-	0.6189	61.89%
CYP2C9 substrate	-	0.5903	59.03%
CYP2D6 substrate	-	0.8263	82.63%
CYP3A4 inhibition	-	0.6981	69.81%
CYP2C9 inhibition	+	0.5111	51.11%
CYP2C19 inhibition	+	0.6690	66.90%
CYP2D6 inhibition	-	0.7527	75.27%
CYP1A2 inhibition	+	0.7886	78.86%
CYP2C8 inhibition	-	0.8506	85.06%
CYP inhibitory promiscuity	+	0.6976	69.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.6936	69.36%
Eye corrosion	-	0.9903	99.03%
Eye irritation	+	0.6345	63.45%
Skin irritation	-	0.7278	72.78%
Skin corrosion	-	0.9522	95.22%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6988	69.88%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.8136	81.36%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6171	61.71%
Acute Oral Toxicity (c)	III	0.3759	37.59%
Estrogen receptor binding	+	0.7570	75.70%
Androgen receptor binding	+	0.7192	71.92%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8952	89.52%
Aromatase binding	+	0.7268	72.68%
PPAR gamma	+	0.8630	86.30%
Honey bee toxicity	-	0.9407	94.07%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	96.43%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.06%	91.49%
CHEMBL2581	P07339	Cathepsin D	93.72%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.42%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.39%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.57%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.34%	99.15%

Plants that contains it

• Ammi majus
• Zanthoxylum spinosum

Cross-Links

• PubChem: 14102503
• NPASS: NPC224816
• LOTUS: LTS0021048
• wikiData: Q105266350