(1R,3S)-5,9,10-trihydroxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromene-6,7-dione

Details

• Internal ID: 5fecf58b-d228-4305-9d29-2f75dd5cf9cb
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: (1R,3S)-5,9,10-trihydroxy-1,3-dimethyl-3,4-dihydro-1H-benzo[g]isochromene-6,7-dione
• SMILES (Canonical): CC1CC2=C(C(O1)C)C(=C3C(=CC(=O)C(=O)C3=C2O)O)O
• SMILES (Isomeric): C[C@H]1CC2=C([C@H](O1)C)C(=C3C(=CC(=O)C(=O)C3=C2O)O)O
• InChI: InChI=1S/C15H14O6/c1-5-3-7-10(6(2)21-5)15(20)11-8(16)4-9(17)14(19)12(11)13(7)18/h4-6,16,18,20H,3H2,1-2H3/t5-,6+/m0/s1
• InChI Key: IEIMXTNIYANNRS-NTSWFWBYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₆
• Molecular Weight: 290.27 g/mol
• Exact Mass: 290.07903816 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.78
• H-Bond Acceptor: 6
• 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	+	0.9228	92.28%
Caco-2	-	0.6924	69.24%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5304	53.04%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.8757	87.57%
OATP1B3 inhibitior	+	0.9657	96.57%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9383	93.83%
P-glycoprotein inhibitior	-	0.9002	90.02%
P-glycoprotein substrate	-	0.7976	79.76%
CYP3A4 substrate	-	0.5096	50.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8469	84.69%
CYP3A4 inhibition	-	0.5799	57.99%
CYP2C9 inhibition	+	0.5797	57.97%
CYP2C19 inhibition	-	0.6460	64.60%
CYP2D6 inhibition	-	0.7661	76.61%
CYP1A2 inhibition	+	0.7681	76.81%
CYP2C8 inhibition	-	0.9431	94.31%
CYP inhibitory promiscuity	-	0.5215	52.15%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5856	58.56%
Eye corrosion	-	0.9869	98.69%
Eye irritation	+	0.5983	59.83%
Skin irritation	-	0.6384	63.84%
Skin corrosion	-	0.8889	88.89%
Ames mutagenesis	+	0.6472	64.72%
Human Ether-a-go-go-Related Gene inhibition	-	0.7807	78.07%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.6283	62.83%
skin sensitisation	-	0.6791	67.91%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6028	60.28%
Acute Oral Toxicity (c)	I	0.3753	37.53%
Estrogen receptor binding	+	0.6811	68.11%
Androgen receptor binding	+	0.5348	53.48%
Thyroid receptor binding	-	0.6457	64.57%
Glucocorticoid receptor binding	+	0.8409	84.09%
Aromatase binding	-	0.5911	59.11%
PPAR gamma	+	0.6476	64.76%
Honey bee toxicity	-	0.9197	91.97%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9609	96.09%

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	98.36%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.42%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.86%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.10%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	86.58%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.56%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.65%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.38%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.64%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.50%	100.00%

Plants that contains it

• Capillipedium parviflorum
• Hyptis spicigera
• Quercus agrifolia
• Salvia sclarea
• Vitis rotundifolia

Cross-Links

• PubChem: 11109030
• LOTUS: LTS0140661
• wikiData: Q81976693