[(1S,4aR,5R,7S,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 4-hydroxybenzoate

Details

• Internal ID: 0a0548b3-71fa-4f4e-b10a-e4fea2725ea8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,5R,7S,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[(2S,3S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 4-hydroxybenzoate
• InChI: InChI=1S/C22H28O12/c23-8-14-16(26)17(27)18(28)21(33-14)34-20-15-12(5-6-31-20)13(7-22(15,30)9-24)32-19(29)10-1-3-11(25)4-2-10/h1-6,12-18,20-21,23-28,30H,7-9H2/t12-,13+,14?,15+,16-,17?,18-,20-,21-,22+/m0/s1
• InChI Key: OTIAAGNDDJEMIJ-DDJYQZFCSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₁₂
• Molecular Weight: 484.40 g/mol
• Exact Mass: 484.15807632 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -2.04
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5822	58.22%
Caco-2	-	0.9134	91.34%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5469	54.69%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.8186	81.86%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7579	75.79%
P-glycoprotein inhibitior	-	0.7183	71.83%
P-glycoprotein substrate	-	0.6854	68.54%
CYP3A4 substrate	+	0.6746	67.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8464	84.64%
CYP3A4 inhibition	-	0.9197	91.97%
CYP2C9 inhibition	-	0.9482	94.82%
CYP2C19 inhibition	-	0.8346	83.46%
CYP2D6 inhibition	-	0.8656	86.56%
CYP1A2 inhibition	-	0.9075	90.75%
CYP2C8 inhibition	+	0.7269	72.69%
CYP inhibitory promiscuity	-	0.8525	85.25%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5510	55.10%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9469	94.69%
Skin irritation	-	0.7825	78.25%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5225	52.25%
Micronuclear	-	0.5467	54.67%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8181	81.81%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.5825	58.25%
Acute Oral Toxicity (c)	III	0.5135	51.35%
Estrogen receptor binding	+	0.7570	75.70%
Androgen receptor binding	-	0.5084	50.84%
Thyroid receptor binding	+	0.5800	58.00%
Glucocorticoid receptor binding	-	0.5326	53.26%
Aromatase binding	+	0.7168	71.68%
PPAR gamma	+	0.7339	73.39%
Honey bee toxicity	-	0.7724	77.24%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.6642	66.42%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	31 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.23%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.30%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.78%	96.09%
CHEMBL4208	P20618	Proteasome component C5	92.13%	90.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	91.91%	94.97%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.65%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	89.62%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.05%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.29%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.80%	95.83%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.74%	96.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.82%	97.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.73%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.34%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.07%	94.00%
CHEMBL2581	P07339	Cathepsin D	81.49%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	81.08%	90.17%
CHEMBL226	P30542	Adenosine A1 receptor	80.40%	95.93%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.35%	94.00%
CHEMBL3194	P02766	Transthyretin	80.17%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.05%	100.00%

Plants that contains it

• Catalpa ovata

Cross-Links

• PubChem: 163064576
• LOTUS: LTS0139095
• wikiData: Q105199649