(4S,10S)-4,5,6-trihydroxy-4,10-dimethyl-7,8,9,10-tetrahydro-1H-benzo[h]isochromen-3-one

Details

• Internal ID: 93d19b75-afc6-4359-8caa-083546127132
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: (4S,10S)-4,5,6-trihydroxy-4,10-dimethyl-7,8,9,10-tetrahydro-1H-benzo[h]isochromen-3-one
• SMILES (Canonical): CC1CCCC2=C1C3=C(C(=C2O)O)C(C(=O)OC3)(C)O
• SMILES (Isomeric): C[C@H]1CCCC2=C1C3=C(C(=C2O)O)[C@](C(=O)OC3)(C)O
• InChI: InChI=1S/C15H18O5/c1-7-4-3-5-8-10(7)9-6-20-14(18)15(2,19)11(9)13(17)12(8)16/h7,16-17,19H,3-6H2,1-2H3/t7-,15-/m0/s1
• InChI Key: JJAZJHQERFKZAF-ZIDLFYJRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.80
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7934	79.34%
Caco-2	+	0.5793	57.93%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7565	75.65%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.8981	89.81%
OATP1B3 inhibitior	+	0.9256	92.56%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7615	76.15%
P-glycoprotein inhibitior	-	0.9165	91.65%
P-glycoprotein substrate	-	0.8262	82.62%
CYP3A4 substrate	+	0.6059	60.59%
CYP2C9 substrate	+	0.6104	61.04%
CYP2D6 substrate	-	0.7626	76.26%
CYP3A4 inhibition	-	0.8216	82.16%
CYP2C9 inhibition	-	0.8469	84.69%
CYP2C19 inhibition	-	0.8312	83.12%
CYP2D6 inhibition	-	0.9269	92.69%
CYP1A2 inhibition	+	0.7386	73.86%
CYP2C8 inhibition	-	0.7864	78.64%
CYP inhibitory promiscuity	-	0.9376	93.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6868	68.68%
Eye corrosion	-	0.9899	98.99%
Eye irritation	+	0.5990	59.90%
Skin irritation	-	0.6857	68.57%
Skin corrosion	-	0.9224	92.24%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7141	71.41%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8515	85.15%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6402	64.02%
Acute Oral Toxicity (c)	III	0.5355	53.55%
Estrogen receptor binding	+	0.6385	63.85%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5488	54.88%
Glucocorticoid receptor binding	+	0.8492	84.92%
Aromatase binding	-	0.6522	65.22%
PPAR gamma	+	0.5409	54.09%
Honey bee toxicity	-	0.9404	94.04%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9788	97.88%

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	97.72%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.93%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.79%	100.00%
CHEMBL2581	P07339	Cathepsin D	90.66%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.20%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.44%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.44%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.30%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.37%	89.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.25%	90.08%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.08%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.06%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.84%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.01%	96.77%
CHEMBL1951	P21397	Monoamine oxidase A	80.64%	91.49%

Plants that contains it

• Psacalium radulifolium

Cross-Links

• PubChem: 10707712
• LOTUS: LTS0038881
• wikiData: Q105129513