(4aS,8aS)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4a,8a-dihydrochromen-4-one

Details

• Internal ID: 9ff1a19e-7b70-498e-823a-74f955097072
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: (4aS,8aS)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4a,8a-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=C(C(=O)C3C(O2)C=C(C=C3O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=C(C(=O)[C@H]3[C@@H](O2)C=C(C=C3O)O)O)O)O
• InChI: InChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,11-12,16-19,21H/t11-,12+/m0/s1
• InChI Key: XCGZWJIXHMSSQC-NWDGAFQWSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25 g/mol
• Exact Mass: 304.05830272 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.81
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9606	96.06%
Caco-2	-	0.9193	91.93%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5210	52.10%
OATP2B1 inhibitior	-	0.6714	67.14%
OATP1B1 inhibitior	+	0.9352	93.52%
OATP1B3 inhibitior	+	0.9732	97.32%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8737	87.37%
P-glycoprotein inhibitior	-	0.8741	87.41%
P-glycoprotein substrate	-	0.9492	94.92%
CYP3A4 substrate	+	0.5134	51.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8432	84.32%
CYP3A4 inhibition	+	0.7272	72.72%
CYP2C9 inhibition	+	0.6206	62.06%
CYP2C19 inhibition	-	0.7606	76.06%
CYP2D6 inhibition	-	0.9225	92.25%
CYP1A2 inhibition	+	0.8379	83.79%
CYP2C8 inhibition	+	0.4934	49.34%
CYP inhibitory promiscuity	+	0.8513	85.13%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6307	63.07%
Eye corrosion	-	0.9813	98.13%
Eye irritation	+	0.9244	92.44%
Skin irritation	+	0.5542	55.42%
Skin corrosion	-	0.9255	92.55%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7984	79.84%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	+	0.5959	59.59%
skin sensitisation	-	0.5357	53.57%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5847	58.47%
Acute Oral Toxicity (c)	II	0.6795	67.95%
Estrogen receptor binding	+	0.7777	77.77%
Androgen receptor binding	+	0.7107	71.07%
Thyroid receptor binding	+	0.6693	66.93%
Glucocorticoid receptor binding	+	0.7211	72.11%
Aromatase binding	+	0.6995	69.95%
PPAR gamma	+	0.7709	77.09%
Honey bee toxicity	-	0.8067	80.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9422	94.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.00%	99.15%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.39%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.14%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	93.31%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.78%	95.56%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	88.25%	83.10%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.05%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.83%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.24%	85.14%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	83.91%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.53%	99.23%
CHEMBL4530	P00488	Coagulation factor XIII	82.75%	96.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	81.19%	96.12%

Plants that contains it

• Manilkara hexandra

Cross-Links

• PubChem: 162995241
• LOTUS: LTS0165627
• wikiData: Q105325055