Sibiskoside

Details

• Internal ID: 0c3686b8-7c8e-4fa4-9e47-dff3ada18886
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (3Z,5R)-5-(2-methylprop-1-enyl)-3-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylidene]oxolan-2-one
• SMILES (Canonical): CC(=CC1CC(=CCOC2C(C(C(C(O2)CO)O)O)O)C(=O)O1)C
• SMILES (Isomeric): CC(=C[C@H]1C/C(=C/CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)/C(=O)O1)C
• InChI: InChI=1S/C16H24O8/c1-8(2)5-10-6-9(15(21)23-10)3-4-22-16-14(20)13(19)12(18)11(7-17)24-16/h3,5,10-14,16-20H,4,6-7H2,1-2H3/b9-3-/t10-,11+,12+,13-,14+,16+/m0/s1
• InChI Key: AYOGZIXAHOAPOK-QKAQTOFFSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₈
• Molecular Weight: 344.36 g/mol
• Exact Mass: 344.14711772 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.99
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 928326-85-6
• Sibiscoside
• CHEBI:66480
• 1-O-beta-D-glucopyranosyl-geraniol-5,10-olide
• Q27135081
• (2Z)-2-[(5R)-5-(2-methylprop-1-en-1-yl)-2-oxodihydrofuran-3(2H)-ylidene]ethyl beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7092	70.92%
Caco-2	-	0.8658	86.58%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8748	87.48%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.9006	90.06%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8050	80.50%
P-glycoprotein inhibitior	-	0.8549	85.49%
P-glycoprotein substrate	-	0.9142	91.42%
CYP3A4 substrate	+	0.5607	56.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8838	88.38%
CYP3A4 inhibition	-	0.9202	92.02%
CYP2C9 inhibition	-	0.8562	85.62%
CYP2C19 inhibition	-	0.8367	83.67%
CYP2D6 inhibition	-	0.9039	90.39%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	-	0.9034	90.34%
CYP inhibitory promiscuity	-	0.7446	74.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6634	66.34%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9650	96.50%
Skin irritation	-	0.8110	81.10%
Skin corrosion	-	0.9447	94.47%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7941	79.41%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6986	69.86%
skin sensitisation	-	0.8534	85.34%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.6899	68.99%
Acute Oral Toxicity (c)	III	0.6100	61.00%
Estrogen receptor binding	+	0.5536	55.36%
Androgen receptor binding	-	0.5769	57.69%
Thyroid receptor binding	-	0.6027	60.27%
Glucocorticoid receptor binding	-	0.6205	62.05%
Aromatase binding	+	0.5716	57.16%
PPAR gamma	-	0.6382	63.82%
Honey bee toxicity	-	0.6718	67.18%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.7303	73.03%

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	94.90%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.30%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.56%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	86.91%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.54%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.81%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.14%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.46%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.17%	85.14%

Plants that contains it

• Sibiraea angustata

Cross-Links

• PubChem: 70697788
• NPASS: NPC25537
• LOTUS: LTS0252308
• wikiData: Q27135081