Foliosidine

Details

• Internal ID: 71983533-eaee-4fe2-a027-5fe9fceb4471
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Quinolones and derivatives > Hydroquinolones
• IUPAC Name: 8-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-1-methylquinolin-2-one
• SMILES (Canonical): CC(C)(C(COC1=CC=CC2=C1N(C(=O)C=C2OC)C)O)O
• SMILES (Isomeric): CC(C)(C(COC1=CC=CC2=C1N(C(=O)C=C2OC)C)O)O
• InChI: InChI=1S/C16H21NO5/c1-16(2,20)13(18)9-22-11-7-5-6-10-12(21-4)8-14(19)17(3)15(10)11/h5-8,13,18,20H,9H2,1-4H3
• InChI Key: IUPYLWAXGAJZQC-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.34 g/mol
• Exact Mass: 307.14197277 g/mol
• Topological Polar Surface Area (TPSA): 79.20 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.06
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 21300-44-7
• 8-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-1-methylquinolin-2(1H)-one
• 8-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-1-methylquinolin-2-one
• 8-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-1-methyl-2-quinolinone
• SR-01000075880
• Prestwick_1030
• Prestwick0_000667
• Prestwick1_000667
• Prestwick2_000667
• Prestwick3_000667
• CBMicro_015500
• Lopac0_000516
• Oprea1_322850
• Oprea1_658886
• BSPBio_000733
• MLS002153944
• SPBio_002654
• BPBio1_000807
• CHEMBL1450334
• SCHEMBL14029270
• CHEBI:91737
• 8-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-1-methyl-1,2-dihydroquinolin-2-one
• DTXSID501347428
• HMS1570E15
• HMS1648I16
• HMS2097E15
• HMS2235P04
• HMS3371F04
• 8-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-1-methylhydroquinolin-2-one
• AKOS001581089
• AKOS021826870
• CCG-202835
• NCGC00015440-03
• NCGC00015440-04
• NCGC00015440-05
• NCGC00015440-06
• NCGC00093911-01
• NCGC00093911-02
• NCGC00093911-03
• NCGC00179455-01
• SMR001233284
• VS-02586
• BIM-0015491.P001
• CS-0336457
• EU-0100516
• F 6426
• SR-01000075880-1
• SR-01000075880-5
• BRD-A49734948-001-03-3
• BRD-A49734948-001-09-0
• Q27163548

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8844	88.44%
Caco-2	+	0.6673	66.73%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5312	53.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9450	94.50%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6156	61.56%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.5406	54.06%
CYP3A4 substrate	+	0.6183	61.83%
CYP2C9 substrate	-	0.7941	79.41%
CYP2D6 substrate	-	0.8387	83.87%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.7167	71.67%
CYP inhibitory promiscuity	-	0.8062	80.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6498	64.98%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9376	93.76%
Skin irritation	-	0.8220	82.20%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6604	66.04%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.5946	59.46%
skin sensitisation	-	0.8856	88.56%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.8232	82.32%
Acute Oral Toxicity (c)	III	0.6518	65.18%
Estrogen receptor binding	+	0.7915	79.15%
Androgen receptor binding	+	0.6577	65.77%
Thyroid receptor binding	+	0.6859	68.59%
Glucocorticoid receptor binding	+	0.6540	65.40%
Aromatase binding	+	0.5198	51.98%
PPAR gamma	+	0.7189	71.89%
Honey bee toxicity	-	0.9084	90.84%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	3.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.09%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.14%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.42%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.93%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.45%	86.33%
CHEMBL2535	P11166	Glucose transporter	94.38%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.99%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.59%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.76%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.64%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.29%	99.17%
CHEMBL1907	P15144	Aminopeptidase N	87.08%	93.31%
CHEMBL213	P08588	Beta-1 adrenergic receptor	86.17%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.23%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.82%	89.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.68%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	81.30%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.76%	97.25%

Plants that contains it

• Haplophyllum griffithianum

Cross-Links

• PubChem: 2837663
• LOTUS: LTS0110382
• wikiData: Q27163548