14-Hydroxyaflaquinolone F

Details

• Internal ID: 8c62e3f7-254b-4365-b16d-cf989eb0c8e7
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Phenylquinolines
• IUPAC Name: (3S,4S)-3,4-dihydroxy-4-(4-hydroxyphenyl)-1,3-dihydroquinolin-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C(C(C(=O)N2)O)(C3=CC=C(C=C3)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)[C@]([C@@H](C(=O)N2)O)(C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C15H13NO4/c17-10-7-5-9(6-8-10)15(20)11-3-1-2-4-12(11)16-14(19)13(15)18/h1-8,13,17-18,20H,(H,16,19)/t13-,15+/m1/s1
• InChI Key: KCCQWQGKTHFIKZ-HIFRSBDPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₃NO₄
• Molecular Weight: 271.27 g/mol
• Exact Mass: 271.08445790 g/mol
• Topological Polar Surface Area (TPSA): 89.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.94
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• (3S,4S)-3,4-dihydroxy-4-(4-hydroxyphenyl)-1,3-dihydroquinolin-2-one
• RefChem:78640
• CHEMBL2431785
• CHEBI:203998

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9224	92.24%
Caco-2	-	0.6799	67.99%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6108	61.08%
OATP2B1 inhibitior	-	0.7260	72.60%
OATP1B1 inhibitior	+	0.8624	86.24%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5706	57.06%
P-glycoprotein inhibitior	-	0.9293	92.93%
P-glycoprotein substrate	-	0.8294	82.94%
CYP3A4 substrate	-	0.5052	50.52%
CYP2C9 substrate	-	0.5976	59.76%
CYP2D6 substrate	-	0.7842	78.42%
CYP3A4 inhibition	-	0.7168	71.68%
CYP2C9 inhibition	-	0.7313	73.13%
CYP2C19 inhibition	-	0.7064	70.64%
CYP2D6 inhibition	-	0.8821	88.21%
CYP1A2 inhibition	+	0.5735	57.35%
CYP2C8 inhibition	-	0.6305	63.05%
CYP inhibitory promiscuity	-	0.7060	70.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7189	71.89%
Eye corrosion	-	0.9953	99.53%
Eye irritation	-	0.5633	56.33%
Skin irritation	-	0.7855	78.55%
Skin corrosion	-	0.9571	95.71%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8793	87.93%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.6714	67.14%
skin sensitisation	-	0.8443	84.43%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7637	76.37%
Acute Oral Toxicity (c)	III	0.4369	43.69%
Estrogen receptor binding	+	0.6449	64.49%
Androgen receptor binding	+	0.8275	82.75%
Thyroid receptor binding	+	0.6473	64.73%
Glucocorticoid receptor binding	+	0.7442	74.42%
Aromatase binding	+	0.5694	56.94%
PPAR gamma	+	0.8671	86.71%
Honey bee toxicity	-	0.9241	92.41%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.4150	41.50%

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	98.05%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.37%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.47%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.19%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	88.40%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.90%	99.23%
CHEMBL4208	P20618	Proteasome component C5	84.60%	90.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	83.55%	90.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.07%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.24%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 72703677
• LOTUS: LTS0035640
• wikiData: Q77382754