Glycocitrine II

Details

• Internal ID: b43ee93a-b961-4834-aea9-7cf9c8a7751f
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: 1,3-dihydroxy-10-methyl-4-(3-methylbut-2-enyl)acridin-9-one
• SMILES (Canonical): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C3=CC=CC=C3N2C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=C(C=C1O)O)C(=O)C3=CC=CC=C3N2C)C
• InChI: InChI=1S/C19H19NO3/c1-11(2)8-9-13-15(21)10-16(22)17-18(13)20(3)14-7-5-4-6-12(14)19(17)23/h4-8,10,21-22H,9H2,1-3H3
• InChI Key: ZVEGIYHOVGYFQS-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₃
• Molecular Weight: 309.40 g/mol
• Exact Mass: 309.13649347 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 3.61
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• CHEMBL451704
• 1,3-dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10h)-acridinone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	+	0.9372	93.72%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Nucleus	0.6120	61.20%
OATP2B1 inhibitior	-	0.5757	57.57%
OATP1B1 inhibitior	+	0.9142	91.42%
OATP1B3 inhibitior	+	0.9297	92.97%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5720	57.20%
P-glycoprotein inhibitior	-	0.6837	68.37%
P-glycoprotein substrate	-	0.6892	68.92%
CYP3A4 substrate	+	0.5510	55.10%
CYP2C9 substrate	+	0.6000	60.00%
CYP2D6 substrate	-	0.8525	85.25%
CYP3A4 inhibition	-	0.8079	80.79%
CYP2C9 inhibition	-	0.6226	62.26%
CYP2C19 inhibition	+	0.5495	54.95%
CYP2D6 inhibition	-	0.5621	56.21%
CYP1A2 inhibition	+	0.7605	76.05%
CYP2C8 inhibition	-	0.8626	86.26%
CYP inhibitory promiscuity	+	0.7885	78.85%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4996	49.96%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.5877	58.77%
Skin irritation	-	0.8107	81.07%
Skin corrosion	-	0.9367	93.67%
Ames mutagenesis	+	0.7836	78.36%
Human Ether-a-go-go-Related Gene inhibition	+	0.7239	72.39%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.5015	50.15%
skin sensitisation	-	0.8336	83.36%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8666	86.66%
Acute Oral Toxicity (c)	III	0.6773	67.73%
Estrogen receptor binding	+	0.7711	77.11%
Androgen receptor binding	+	0.6102	61.02%
Thyroid receptor binding	+	0.6919	69.19%
Glucocorticoid receptor binding	+	0.8535	85.35%
Aromatase binding	+	0.5656	56.56%
PPAR gamma	+	0.8901	89.01%
Honey bee toxicity	-	0.9270	92.70%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9158	91.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.75%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.32%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	96.98%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.57%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	94.34%	93.99%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.15%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.02%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.11%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.94%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.23%	96.09%
CHEMBL255	P29275	Adenosine A2b receptor	82.95%	98.59%
CHEMBL4208	P20618	Proteasome component C5	80.29%	90.00%

Plants that contains it

• Glycosmis parviflora

Cross-Links

• PubChem: 11781835
• LOTUS: LTS0005029
• wikiData: Q104666966