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

Details

• Internal ID: ac1659b3-1878-4cbc-ac30-e649e8a4fd7f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(1R,4aR,5S,7aS)-1-hydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): C1C(C(C(C(O1)OC2C=C(C3C2C=COC3O)COC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2C=C([C@@H]3[C@H]2C=CO[C@H]3O)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C20H30O13/c21-4-11-14(24)15(25)17(27)20(33-11)30-5-7-3-10(8-1-2-29-18(28)12(7)8)32-19-16(26)13(23)9(22)6-31-19/h1-3,8-28H,4-6H2/t8-,9+,10+,11+,12+,13-,14+,15-,16+,17+,18+,19-,20+/m0/s1
• InChI Key: YPNROBCFFPTTOX-XHJGLNSKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₁₃
• Molecular Weight: 478.40 g/mol
• Exact Mass: 478.16864101 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: -4.60
• Atomic LogP (AlogP): -4.34
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 6

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	-	0.8772	87.72%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5196	51.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8603	86.03%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9102	91.02%
P-glycoprotein inhibitior	-	0.7505	75.05%
P-glycoprotein substrate	-	0.7371	73.71%
CYP3A4 substrate	+	0.6084	60.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8337	83.37%
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	-	0.5719	57.19%
CYP inhibitory promiscuity	-	0.8302	83.02%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6696	66.96%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9370	93.70%
Skin irritation	-	0.8094	80.94%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	+	0.5009	50.09%
Human Ether-a-go-go-Related Gene inhibition	+	0.7193	71.93%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	-	0.8177	81.77%
skin sensitisation	-	0.8883	88.83%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7547	75.47%
Acute Oral Toxicity (c)	IV	0.3755	37.55%
Estrogen receptor binding	-	0.5399	53.99%
Androgen receptor binding	-	0.5515	55.15%
Thyroid receptor binding	-	0.4897	48.97%
Glucocorticoid receptor binding	-	0.6156	61.56%
Aromatase binding	+	0.6149	61.49%
PPAR gamma	+	0.6119	61.19%
Honey bee toxicity	-	0.7488	74.88%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
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	98.49%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	95.32%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.11%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.95%	97.09%
CHEMBL4208	P20618	Proteasome component C5	83.32%	90.00%
CHEMBL3589	P55263	Adenosine kinase	81.75%	98.05%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.36%	86.92%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.02%	92.94%

Plants that contains it

• Verbascum thapsus

Cross-Links

• PubChem: 162970149
• LOTUS: LTS0233618
• wikiData: Q105351751