7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5,6,7-triol

Details

• Internal ID: 71cc8698-b799-4b9b-828b-177f20799f0a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5,6,7-triol
• SMILES (Canonical): C1=COC(C2C1C(C(C2(CO)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C1=COC(C2C1C(C(C2(CO)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C15H24O11/c16-3-6-9(19)10(20)11(21)14(25-6)26-13-7-5(1-2-24-13)8(18)12(22)15(7,23)4-17/h1-2,5-14,16-23H,3-4H2
• InChI Key: KZZZOJWMRBMLKD-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₁₁
• Molecular Weight: 380.34 g/mol
• Exact Mass: 380.13186158 g/mol
• Topological Polar Surface Area (TPSA): 190.00 Ų
• XlogP: -3.70
• Atomic LogP (AlogP): -4.64
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• 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	-	0.8949	89.49%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4864	48.64%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8614	86.14%
OATP1B3 inhibitior	+	0.9606	96.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9808	98.08%
P-glycoprotein inhibitior	-	0.8718	87.18%
P-glycoprotein substrate	-	0.9188	91.88%
CYP3A4 substrate	+	0.5313	53.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8355	83.55%
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	-	0.7812	78.12%
CYP inhibitory promiscuity	-	0.9008	90.08%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5947	59.47%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9764	97.64%
Skin irritation	-	0.8217	82.17%
Skin corrosion	-	0.9550	95.50%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5500	55.00%
Micronuclear	-	0.7341	73.41%
Hepatotoxicity	-	0.8625	86.25%
skin sensitisation	-	0.8918	89.18%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.4945	49.45%
Acute Oral Toxicity (c)	IV	0.3764	37.64%
Estrogen receptor binding	-	0.7698	76.98%
Androgen receptor binding	-	0.6304	63.04%
Thyroid receptor binding	-	0.5097	50.97%
Glucocorticoid receptor binding	-	0.7503	75.03%
Aromatase binding	+	0.6465	64.65%
PPAR gamma	+	0.6716	67.16%
Honey bee toxicity	-	0.7674	76.74%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7050	70.50%
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	96.72%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.36%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.47%	86.92%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.25%	94.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.10%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.69%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	80.58%	83.82%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.56%	89.67%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.43%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.41%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	80.30%	95.93%

Plants that contains it

• Paulownia tomentosa
• Scutellaria albida

Cross-Links

• PubChem: 14447032
• LOTUS: LTS0192305
• wikiData: Q104402648