(2S,3R,4S,5S,6R)-2-[[(1S,4aR,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-4a,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: d0215bab-f6ff-4c3f-aef5-cadf5248e789
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,4aR,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-4a,7a-dihydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1=CC(C2C1C=COC2OC3C(C(C(C(O3)CO)O)O)O)(CO)O
• SMILES (Isomeric): C1=C[C@@]([C@@H]2[C@H]1C=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)(CO)O
• InChI: InChI=1S/C15H22O9/c16-5-8-10(18)11(19)12(20)14(23-8)24-13-9-7(2-4-22-13)1-3-15(9,21)6-17/h1-4,7-14,16-21H,5-6H2/t7-,8-,9-,10-,11+,12-,13+,14+,15+/m1/s1
• InChI Key: QZDZJFPCACBGIO-RICUOZJWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₉
• Molecular Weight: 346.33 g/mol
• Exact Mass: 346.12638228 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.80
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7433	74.33%
Caco-2	-	0.8162	81.62%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4864	48.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8876	88.76%
OATP1B3 inhibitior	+	0.9606	96.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9757	97.57%
P-glycoprotein inhibitior	-	0.8767	87.67%
P-glycoprotein substrate	-	0.9088	90.88%
CYP3A4 substrate	+	0.5633	56.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8373	83.73%
CYP3A4 inhibition	-	0.9562	95.62%
CYP2C9 inhibition	-	0.9530	95.30%
CYP2C19 inhibition	-	0.8275	82.75%
CYP2D6 inhibition	-	0.9009	90.09%
CYP1A2 inhibition	-	0.9211	92.11%
CYP2C8 inhibition	-	0.7671	76.71%
CYP inhibitory promiscuity	-	0.9008	90.08%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5947	59.47%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9738	97.38%
Skin irritation	-	0.8217	82.17%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6267	62.67%
Micronuclear	-	0.7341	73.41%
Hepatotoxicity	-	0.8450	84.50%
skin sensitisation	-	0.8918	89.18%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.5740	57.40%
Acute Oral Toxicity (c)	IV	0.3764	37.64%
Estrogen receptor binding	-	0.7799	77.99%
Androgen receptor binding	-	0.6237	62.37%
Thyroid receptor binding	+	0.5199	51.99%
Glucocorticoid receptor binding	-	0.6392	63.92%
Aromatase binding	+	0.5220	52.20%
PPAR gamma	+	0.6461	64.61%
Honey bee toxicity	-	0.7306	73.06%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.7510	75.10%

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	92.08%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.75%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.73%	86.92%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.59%	97.25%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.32%	95.83%
CHEMBL4040	P28482	MAP kinase ERK2	83.53%	83.82%
CHEMBL226	P30542	Adenosine A1 receptor	82.60%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.37%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.49%	97.09%

Plants that contains it

• Eranthemum pulchellum

Cross-Links

• PubChem: 13969558
• LOTUS: LTS0231615
• wikiData: Q105231898