Citrifoside

Details

• Internal ID: 811ac9cb-f0e6-4ab2-b09a-ba73e495bf92
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: methyl (1S,4aS,7S,7aS)-7-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1C=CC2O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C=C[C@@H]2O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C16H22O10/c1-23-14(22)7-5-24-15(10-6(7)2-3-8(10)18)26-16-13(21)12(20)11(19)9(4-17)25-16/h2-3,5-6,8-13,15-21H,4H2,1H3/t6-,8+,9-,10+,11-,12+,13-,15+,16+/m1/s1
• InChI Key: XYYMELWQHNGIOY-OSNMJEOSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₀
• Molecular Weight: 374.34 g/mol
• Exact Mass: 374.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -1.90
• Atomic LogP (AlogP): -2.62
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• methyl (1S,4aS,7S,7aS)-7-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5989	59.89%
Caco-2	-	0.8963	89.63%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6729	67.29%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.7585	75.85%
OATP1B3 inhibitior	+	0.9688	96.88%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9483	94.83%
P-glycoprotein inhibitior	-	0.8992	89.92%
P-glycoprotein substrate	-	0.8706	87.06%
CYP3A4 substrate	+	0.5775	57.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8633	86.33%
CYP3A4 inhibition	-	0.9328	93.28%
CYP2C9 inhibition	-	0.9023	90.23%
CYP2C19 inhibition	-	0.8556	85.56%
CYP2D6 inhibition	-	0.9006	90.06%
CYP1A2 inhibition	-	0.8762	87.62%
CYP2C8 inhibition	-	0.6848	68.48%
CYP inhibitory promiscuity	-	0.6895	68.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6877	68.77%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9606	96.06%
Skin irritation	-	0.7895	78.95%
Skin corrosion	-	0.9565	95.65%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6664	66.64%
Micronuclear	-	0.6841	68.41%
Hepatotoxicity	-	0.7851	78.51%
skin sensitisation	-	0.8863	88.63%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.6276	62.76%
Acute Oral Toxicity (c)	III	0.4862	48.62%
Estrogen receptor binding	-	0.5764	57.64%
Androgen receptor binding	-	0.5941	59.41%
Thyroid receptor binding	-	0.5773	57.73%
Glucocorticoid receptor binding	-	0.6369	63.69%
Aromatase binding	-	0.5633	56.33%
PPAR gamma	-	0.6291	62.91%
Honey bee toxicity	-	0.8900	89.00%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	-	0.5855	58.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.46%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.60%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.94%	94.73%
CHEMBL2581	P07339	Cathepsin D	88.10%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.65%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.96%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.49%	86.33%
CHEMBL4208	P20618	Proteasome component C5	81.21%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.01%	86.92%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 16203752
• LOTUS: LTS0216664
• wikiData: Q105344746