8-[(2S)-3-chloro-2-hydroxy-3-methylbutyl]-7-methoxychromen-2-one

Details

• Internal ID: d59372ee-d70b-4fe4-ad2d-9875d462273e
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives
• IUPAC Name: 8-[(2S)-3-chloro-2-hydroxy-3-methylbutyl]-7-methoxychromen-2-one
• SMILES (Canonical): CC(C)(C(CC1=C(C=CC2=C1OC(=O)C=C2)OC)O)Cl
• SMILES (Isomeric): CC(C)([C@H](CC1=C(C=CC2=C1OC(=O)C=C2)OC)O)Cl
• InChI: InChI=1S/C15H17ClO4/c1-15(2,16)12(17)8-10-11(19-3)6-4-9-5-7-13(18)20-14(9)10/h4-7,12,17H,8H2,1-3H3/t12-/m0/s1
• InChI Key: OSKJVDPXHKUPIU-LBPRGKRZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₇ClO₄
• Molecular Weight: 296.74 g/mol
• Exact Mass: 296.0815367 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.72
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9924	99.24%
Caco-2	+	0.6582	65.82%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5161	51.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9271	92.71%
OATP1B3 inhibitior	+	0.9121	91.21%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.8458	84.58%
P-glycoprotein substrate	-	0.8638	86.38%
CYP3A4 substrate	-	0.5334	53.34%
CYP2C9 substrate	-	0.6435	64.35%
CYP2D6 substrate	-	0.7857	78.57%
CYP3A4 inhibition	-	0.8689	86.89%
CYP2C9 inhibition	-	0.8208	82.08%
CYP2C19 inhibition	-	0.7878	78.78%
CYP2D6 inhibition	-	0.9141	91.41%
CYP1A2 inhibition	-	0.6833	68.33%
CYP2C8 inhibition	-	0.6824	68.24%
CYP inhibitory promiscuity	-	0.8135	81.35%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.8074	80.74%
Carcinogenicity (trinary)	Non-required	0.5461	54.61%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9311	93.11%
Skin irritation	-	0.7484	74.84%
Skin corrosion	-	0.9268	92.68%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7586	75.86%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.8463	84.63%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6125	61.25%
Acute Oral Toxicity (c)	III	0.5223	52.23%
Estrogen receptor binding	+	0.8108	81.08%
Androgen receptor binding	-	0.4926	49.26%
Thyroid receptor binding	+	0.6603	66.03%
Glucocorticoid receptor binding	+	0.6787	67.87%
Aromatase binding	-	0.5113	51.13%
PPAR gamma	+	0.9388	93.88%
Honey bee toxicity	-	0.8734	87.34%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6253	62.53%
Fish aquatic toxicity	+	0.9711	97.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.05%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.84%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.78%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.65%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.05%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.86%	86.92%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	82.77%	92.29%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.16%	89.62%
CHEMBL1255126	O15151	Protein Mdm4	82.07%	90.20%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.67%	96.95%
CHEMBL4040	P28482	MAP kinase ERK2	81.46%	83.82%
CHEMBL2535	P11166	Glucose transporter	81.19%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.10%	99.17%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.68%	100.00%

Plants that contains it

• Murraya paniculata

Cross-Links

• PubChem: 162920995
• LOTUS: LTS0046886
• wikiData: Q105199026