2-[[5-[3,5-Dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 644945a0-1867-4ed4-9de7-8bb52745b0b7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 2-[[5-[3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(C(O1)OC2C(C(OC(C2O)OC3C=C(C4C3C=COC4OC5C(C(C(C(O5)CO)O)O)O)CO)CO)O)O)O)O
• SMILES (Isomeric): C1C(C(C(C(O1)OC2C(C(OC(C2O)OC3C=C(C4C3C=COC4OC5C(C(C(C(O5)CO)O)O)O)CO)CO)O)O)O)O
• InChI: InChI=1S/C26H40O18/c27-4-8-3-11(9-1-2-38-23(14(8)9)44-25-20(36)18(34)16(32)12(5-28)41-25)40-26-21(37)22(17(33)13(6-29)42-26)43-24-19(35)15(31)10(30)7-39-24/h1-3,9-37H,4-7H2
• InChI Key: QUZVTQBKZOPMMB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₁₈
• Molecular Weight: 640.60 g/mol
• Exact Mass: 640.22146442 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: -6.10
• Atomic LogP (AlogP): -6.51
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6447	64.47%
Caco-2	-	0.8967	89.67%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5196	51.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8611	86.11%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7694	76.94%
P-glycoprotein inhibitior	-	0.5767	57.67%
P-glycoprotein substrate	-	0.6948	69.48%
CYP3A4 substrate	+	0.6233	62.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8272	82.72%
CYP3A4 inhibition	-	0.9423	94.23%
CYP2C9 inhibition	-	0.9333	93.33%
CYP2C19 inhibition	-	0.8160	81.60%
CYP2D6 inhibition	-	0.8640	86.40%
CYP1A2 inhibition	-	0.8733	87.33%
CYP2C8 inhibition	-	0.6537	65.37%
CYP inhibitory promiscuity	-	0.8302	83.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6696	66.96%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9133	91.33%
Skin irritation	-	0.8094	80.94%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	-	0.5191	51.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7814	78.14%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.9052	90.52%
skin sensitisation	-	0.8883	88.83%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7849	78.49%
Acute Oral Toxicity (c)	IV	0.3755	37.55%
Estrogen receptor binding	+	0.6709	67.09%
Androgen receptor binding	+	0.5410	54.10%
Thyroid receptor binding	-	0.5070	50.70%
Glucocorticoid receptor binding	-	0.7281	72.81%
Aromatase binding	+	0.6475	64.75%
PPAR gamma	+	0.6473	64.73%
Honey bee toxicity	-	0.6941	69.41%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6950	69.50%
Fish aquatic toxicity	-	0.6539	65.39%

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	98.69%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	92.51%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.76%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.95%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.08%	86.92%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	84.23%	80.33%
CHEMBL3589	P55263	Adenosine kinase	83.23%	98.05%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.48%	94.00%

Plants that contains it

• Verbascum sinuatum

Cross-Links

• PubChem: 163040396
• LOTUS: LTS0142777
• wikiData: Q105228522