7-hydroxy-6-[(2R)-2-hydroxy-3-(hydroxymethyl)but-3-enyl]chromen-2-one

Details

• Internal ID: 14322225-340f-4b04-9a8c-2b8ae5eaebce
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 7-hydroxycoumarins
• IUPAC Name: 7-hydroxy-6-[(2R)-2-hydroxy-3-(hydroxymethyl)but-3-enyl]chromen-2-one
• SMILES (Canonical): C=C(CO)C(CC1=C(C=C2C(=C1)C=CC(=O)O2)O)O
• SMILES (Isomeric): C=C(CO)[C@@H](CC1=C(C=C2C(=C1)C=CC(=O)O2)O)O
• InChI: InChI=1S/C14H14O5/c1-8(7-15)11(16)5-10-4-9-2-3-14(18)19-13(9)6-12(10)17/h2-4,6,11,15-17H,1,5,7H2/t11-/m1/s1
• InChI Key: GPMDKNUJKCRHQS-LLVKDONJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.26 g/mol
• Exact Mass: 262.08412354 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.95
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9153	91.53%
Caco-2	-	0.5797	57.97%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6277	62.77%
OATP2B1 inhibitior	-	0.7115	71.15%
OATP1B1 inhibitior	+	0.8974	89.74%
OATP1B3 inhibitior	+	0.9255	92.55%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8422	84.22%
P-glycoprotein inhibitior	-	0.9500	95.00%
P-glycoprotein substrate	-	0.8441	84.41%
CYP3A4 substrate	-	0.5847	58.47%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.7999	79.99%
CYP3A4 inhibition	-	0.6490	64.90%
CYP2C9 inhibition	-	0.8150	81.50%
CYP2C19 inhibition	-	0.5688	56.88%
CYP2D6 inhibition	-	0.8061	80.61%
CYP1A2 inhibition	-	0.7308	73.08%
CYP2C8 inhibition	-	0.7882	78.82%
CYP inhibitory promiscuity	-	0.5926	59.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7193	71.93%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.7480	74.80%
Skin corrosion	-	0.9505	95.05%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6191	61.91%
Micronuclear	+	0.5959	59.59%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.7349	73.49%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.5906	59.06%
Acute Oral Toxicity (c)	III	0.3831	38.31%
Estrogen receptor binding	-	0.4920	49.20%
Androgen receptor binding	+	0.5705	57.05%
Thyroid receptor binding	-	0.5237	52.37%
Glucocorticoid receptor binding	+	0.7577	75.77%
Aromatase binding	+	0.7049	70.49%
PPAR gamma	+	0.8311	83.11%
Honey bee toxicity	-	0.8984	89.84%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9811	98.11%

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	99.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.87%	98.95%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.56%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.63%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.90%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.34%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	84.07%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.35%	99.15%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.15%	85.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.96%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.67%	99.17%

Plants that contains it

• Achyrocline alata
• Aegle marmelos
• Baccharis intermixta
• Lasiolaena santosii

Cross-Links

• PubChem: 162867118
• LOTUS: LTS0157798
• wikiData: Q105215222