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

Details

• Internal ID: e60c7107-f292-4bc1-9fb2-41e43e384169
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[[(1S,4aS,6S,7S,7aS)-6-hydroxy-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C)OC3C(C(C(C(O3)CO)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
• InChI: InChI=1S/C16H26O8/c1-6-5-22-15(11-7(2)9(18)3-8(6)11)24-16-14(21)13(20)12(19)10(4-17)23-16/h5,7-21H,3-4H2,1-2H3/t7-,8-,9+,10-,11-,12-,13+,14-,15+,16+/m1/s1
• InChI Key: CGTBKKCAKWNILX-WDBUIPMMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₈
• Molecular Weight: 346.37 g/mol
• Exact Mass: 346.16276778 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.30
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6177	61.77%
Caco-2	-	0.8737	87.37%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5479	54.79%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	-	0.3994	39.94%
OATP1B3 inhibitior	+	0.9522	95.22%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9327	93.27%
P-glycoprotein inhibitior	-	0.8893	88.93%
P-glycoprotein substrate	-	0.8474	84.74%
CYP3A4 substrate	+	0.5551	55.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8214	82.14%
CYP3A4 inhibition	-	0.9022	90.22%
CYP2C9 inhibition	-	0.9218	92.18%
CYP2C19 inhibition	-	0.9054	90.54%
CYP2D6 inhibition	-	0.8918	89.18%
CYP1A2 inhibition	-	0.8345	83.45%
CYP2C8 inhibition	-	0.7801	78.01%
CYP inhibitory promiscuity	-	0.8191	81.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7099	70.99%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9881	98.81%
Skin irritation	-	0.7385	73.85%
Skin corrosion	-	0.9518	95.18%
Ames mutagenesis	-	0.6398	63.98%
Human Ether-a-go-go-Related Gene inhibition	-	0.4404	44.04%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7427	74.27%
skin sensitisation	-	0.8845	88.45%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8595	85.95%
Acute Oral Toxicity (c)	III	0.4602	46.02%
Estrogen receptor binding	-	0.6631	66.31%
Androgen receptor binding	-	0.6091	60.91%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.7635	76.35%
Aromatase binding	-	0.5270	52.70%
PPAR gamma	+	0.5805	58.05%
Honey bee toxicity	-	0.8611	86.11%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.3708	37.08%

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	94.53%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.30%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.29%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.48%	97.25%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.08%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	89.96%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.07%	96.61%
CHEMBL4208	P20618	Proteasome component C5	86.46%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.61%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.11%	99.17%
CHEMBL2581	P07339	Cathepsin D	81.60%	98.95%

Plants that contains it

• Linaria japonica

Cross-Links

• PubChem: 163008870
• LOTUS: LTS0007932
• wikiData: Q104958151