1-[6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: c0835878-b8aa-4185-ae58-a202709883ac
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 1-[6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1(C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O)O)O
• SMILES (Isomeric): CC1(C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O)O)O
• InChI: InChI=1S/C25H30O14/c1-25(35)16(28)7-11-12(22(33)34)8-37-23(18(11)25)39-24-21(32)20(31)19(30)15(38-24)9-36-17(29)5-3-10-2-4-13(26)14(27)6-10/h2-6,8,11,15-16,18-21,23-24,26-28,30-32,35H,7,9H2,1H3,(H,33,34)
• InChI Key: YHZBVXGYEGLXCQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₄
• Molecular Weight: 554.50 g/mol
• Exact Mass: 554.16355563 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.45
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8673	86.73%
Caco-2	-	0.8980	89.80%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6410	64.10%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.8078	80.78%
OATP1B3 inhibitior	+	0.9467	94.67%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6030	60.30%
P-glycoprotein inhibitior	-	0.6288	62.88%
P-glycoprotein substrate	-	0.6460	64.60%
CYP3A4 substrate	+	0.6735	67.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8773	87.73%
CYP3A4 inhibition	-	0.9244	92.44%
CYP2C9 inhibition	-	0.7278	72.78%
CYP2C19 inhibition	-	0.7763	77.63%
CYP2D6 inhibition	-	0.8785	87.85%
CYP1A2 inhibition	-	0.6926	69.26%
CYP2C8 inhibition	+	0.7182	71.82%
CYP inhibitory promiscuity	-	0.7971	79.71%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6175	61.75%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9322	93.22%
Skin irritation	-	0.6984	69.84%
Skin corrosion	-	0.9281	92.81%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3708	37.08%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7940	79.40%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.9142	91.42%
Acute Oral Toxicity (c)	III	0.3798	37.98%
Estrogen receptor binding	+	0.7604	76.04%
Androgen receptor binding	+	0.6587	65.87%
Thyroid receptor binding	+	0.5763	57.63%
Glucocorticoid receptor binding	+	0.6625	66.25%
Aromatase binding	+	0.5584	55.84%
PPAR gamma	+	0.7104	71.04%
Honey bee toxicity	-	0.7732	77.32%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9621	96.21%

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	99.49%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.49%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.41%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.00%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.64%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.15%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.78%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.26%	95.56%
CHEMBL4208	P20618	Proteasome component C5	92.11%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	91.99%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.89%	96.95%
CHEMBL3194	P02766	Transthyretin	90.81%	90.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.25%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.69%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.59%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.57%	99.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.72%	85.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.64%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	81.78%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	81.53%	94.73%
CHEMBL5028	O14672	ADAM10	81.28%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.01%	100.00%

Plants that contains it

• Lippia origanoides

Cross-Links

• PubChem: 163042891
• LOTUS: LTS0143034
• wikiData: Q105348689