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

Details

• Internal ID: 60c92f58-3a96-46a7-a23c-0ff8bda556b4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [6-chloro-7-hydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 3,4-dihydroxybenzoate
• SMILES (Canonical): C1=COC(C2C1C(C(C2(CO)O)Cl)OC(=O)C3=CC(=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): C1=COC(C2C1C(C(C2(CO)O)Cl)OC(=O)C3=CC(=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O
• InChI: InChI=1S/C22H27ClO13/c23-18-17(35-19(31)8-1-2-10(26)11(27)5-8)9-3-4-33-20(13(9)22(18,32)7-25)36-21-16(30)15(29)14(28)12(6-24)34-21/h1-5,9,12-18,20-21,24-30,32H,6-7H2
• InChI Key: MTRQBGBLTPNJPL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₇ClO₁₃
• Molecular Weight: 534.90 g/mol
• Exact Mass: 534.1140186 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.11
• 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	+	0.7846	78.46%
Caco-2	-	0.9233	92.33%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.5152	51.52%
OATP2B1 inhibitior	-	0.7174	71.74%
OATP1B1 inhibitior	+	0.7896	78.96%
OATP1B3 inhibitior	+	0.9372	93.72%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6602	66.02%
P-glycoprotein inhibitior	-	0.6568	65.68%
P-glycoprotein substrate	-	0.7282	72.82%
CYP3A4 substrate	+	0.6564	65.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8548	85.48%
CYP3A4 inhibition	-	0.8480	84.80%
CYP2C9 inhibition	-	0.8368	83.68%
CYP2C19 inhibition	-	0.6965	69.65%
CYP2D6 inhibition	-	0.7751	77.51%
CYP1A2 inhibition	-	0.7958	79.58%
CYP2C8 inhibition	+	0.6672	66.72%
CYP inhibitory promiscuity	-	0.6679	66.79%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.8338	83.38%
Carcinogenicity (trinary)	Non-required	0.4829	48.29%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9371	93.71%
Skin irritation	-	0.7554	75.54%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5393	53.93%
Hepatotoxicity	-	0.7074	70.74%
skin sensitisation	-	0.7894	78.94%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6204	62.04%
Acute Oral Toxicity (c)	III	0.4793	47.93%
Estrogen receptor binding	+	0.7129	71.29%
Androgen receptor binding	-	0.4821	48.21%
Thyroid receptor binding	+	0.5878	58.78%
Glucocorticoid receptor binding	+	0.5838	58.38%
Aromatase binding	+	0.6630	66.30%
PPAR gamma	+	0.7095	70.95%
Honey bee toxicity	-	0.6592	65.92%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.8919	89.19%

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	99.33%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.77%	91.49%
CHEMBL4208	P20618	Proteasome component C5	93.03%	90.00%
CHEMBL3194	P02766	Transthyretin	92.91%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.42%	86.33%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.76%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.87%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.90%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.43%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.97%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.97%	99.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.18%	97.21%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.14%	96.90%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.33%	92.94%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.80%	96.61%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.92%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.78%	92.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.46%	95.83%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.43%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.16%	89.67%
CHEMBL2581	P07339	Cathepsin D	81.08%	98.95%

Plants that contains it

• Veronica longifolia

Cross-Links

• PubChem: 75244302
• LOTUS: LTS0258009
• wikiData: Q105171840