2-[(3S)-10-hydroxy-1-methyl-9-oxo-3,4-dihydrobenzo[g]isochromen-3-yl]acetic acid

Details

• Internal ID: 11ee8b1d-1ac4-423d-a197-e9af5ef1d480
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 2-[(3S)-10-hydroxy-1-methyl-9-oxo-3,4-dihydrobenzo[g]isochromen-3-yl]acetic acid
• SMILES (Canonical): CC1=C2C(=CC3=CC=CC(=O)C3=C2O)CC(O1)CC(=O)O
• SMILES (Isomeric): CC1=C2C(=CC3=CC=CC(=O)C3=C2O)C[C@H](O1)CC(=O)O
• InChI: InChI=1S/C16H14O5/c1-8-14-10(6-11(21-8)7-13(18)19)5-9-3-2-4-12(17)15(9)16(14)20/h2-5,11,20H,6-7H2,1H3,(H,18,19)/t11-/m0/s1
• InChI Key: YFRUSKASGPDFBR-NSHDSACASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 0.47
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9706	97.06%
Caco-2	-	0.5543	55.43%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7881	78.81%
OATP2B1 inhibitior	-	0.7220	72.20%
OATP1B1 inhibitior	+	0.8670	86.70%
OATP1B3 inhibitior	+	0.9738	97.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7071	70.71%
P-glycoprotein inhibitior	-	0.9353	93.53%
P-glycoprotein substrate	-	0.7611	76.11%
CYP3A4 substrate	+	0.5428	54.28%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	-	0.8887	88.87%
CYP3A4 inhibition	-	0.6057	60.57%
CYP2C9 inhibition	+	0.7546	75.46%
CYP2C19 inhibition	-	0.7369	73.69%
CYP2D6 inhibition	-	0.7884	78.84%
CYP1A2 inhibition	-	0.7005	70.05%
CYP2C8 inhibition	-	0.7324	73.24%
CYP inhibitory promiscuity	-	0.5530	55.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Danger	0.4524	45.24%
Eye corrosion	-	0.9834	98.34%
Eye irritation	-	0.8449	84.49%
Skin irritation	-	0.6369	63.69%
Skin corrosion	-	0.9253	92.53%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7022	70.22%
Micronuclear	+	0.6600	66.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.6804	68.04%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.8207	82.07%
Acute Oral Toxicity (c)	I	0.4165	41.65%
Estrogen receptor binding	+	0.8030	80.30%
Androgen receptor binding	+	0.6568	65.68%
Thyroid receptor binding	-	0.7673	76.73%
Glucocorticoid receptor binding	+	0.7165	71.65%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6496	64.96%
Honey bee toxicity	-	0.9397	93.97%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9308	93.08%

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	96.66%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.43%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.72%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.64%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.48%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.35%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.68%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.43%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	84.36%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.09%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.73%	93.40%
CHEMBL4208	P20618	Proteasome component C5	83.68%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.00%	95.89%

Plants that contains it

• Elaphoglossum spatulatum

Cross-Links

• PubChem: 443833
• LOTUS: LTS0047301
• wikiData: Q105171082