Uncinoside A

Details

• Internal ID: b9afabcd-fa48-47cd-b631-b973f41023b4
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: 5-hydroxy-2,6,8-trimethyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1=CC(=O)C2=C(O1)C(=C(C(=C2O)C)OC3C(C(C(C(O3)CO)O)O)O)C
• SMILES (Isomeric): CC1=CC(=O)C2=C(O1)C(=C(C(=C2O)C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C
• InChI: InChI=1S/C18H22O9/c1-6-4-9(20)11-12(21)7(2)16(8(3)17(11)25-6)27-18-15(24)14(23)13(22)10(5-19)26-18/h4,10,13-15,18-19,21-24H,5H2,1-3H3/t10-,13-,14+,15-,18+/m1/s1
• InChI Key: SYRSLDAOMRWYGP-MLTZOPNTSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₂O₉
• Molecular Weight: 382.40 g/mol
• Exact Mass: 382.12638228 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.40
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• 5-hydroxy-2,6,8-trimethyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 5-hydroxy-2,6,8-trimethyl-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxychromen-4-one
• RefChem:193057
• 48215-55-0
• CHEMBL2164950
• SCHEMBL30621317

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5728	57.28%
Caco-2	-	0.8348	83.48%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6037	60.37%
OATP2B1 inhibitior	-	0.5623	56.23%
OATP1B1 inhibitior	+	0.8162	81.62%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8191	81.91%
P-glycoprotein inhibitior	-	0.8313	83.13%
P-glycoprotein substrate	-	0.8704	87.04%
CYP3A4 substrate	+	0.5634	56.34%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9477	94.77%
CYP2C9 inhibition	-	0.9554	95.54%
CYP2C19 inhibition	-	0.9402	94.02%
CYP2D6 inhibition	-	0.9496	94.96%
CYP1A2 inhibition	-	0.8238	82.38%
CYP2C8 inhibition	-	0.6869	68.69%
CYP inhibitory promiscuity	-	0.8229	82.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7152	71.52%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9237	92.37%
Skin irritation	-	0.8387	83.87%
Skin corrosion	-	0.9679	96.79%
Ames mutagenesis	+	0.6036	60.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.5410	54.10%
Micronuclear	+	0.5633	56.33%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9202	92.02%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.7878	78.78%
Acute Oral Toxicity (c)	III	0.6521	65.21%
Estrogen receptor binding	+	0.7383	73.83%
Androgen receptor binding	+	0.5820	58.20%
Thyroid receptor binding	+	0.5822	58.22%
Glucocorticoid receptor binding	+	0.6276	62.76%
Aromatase binding	+	0.7221	72.21%
PPAR gamma	+	0.6670	66.70%
Honey bee toxicity	-	0.8245	82.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	+	0.8296	82.96%

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	98.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.30%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.52%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.36%	94.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.32%	89.34%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.01%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.69%	86.92%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.57%	83.57%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.30%	96.21%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.23%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	81.56%	94.45%

Plants that contains it

• Selaginella uncinata

Cross-Links

• PubChem: 10022766
• NPASS: NPC38775
• LOTUS: LTS0044731
• wikiData: Q105263747