[(1S,4aR,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-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: c6c5da95-08d0-4577-9f1a-255aa19a9007
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,7S,7aS)-7-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-5-yl] 4-hydroxybenzoate
• SMILES (Canonical): CC1(CC(C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=CC=C(C=C4)O)O
• SMILES (Isomeric): C[C@@]1(CC([C@H]2[C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C4=CC=C(C=C4)O)O
• InChI: InChI=1S/C22H28O11/c1-22(29)8-13(31-19(28)10-2-4-11(24)5-3-10)12-6-7-30-20(15(12)22)33-21-18(27)17(26)16(25)14(9-23)32-21/h2-7,12-18,20-21,23-27,29H,8-9H2,1H3/t12-,13?,14+,15+,16+,17-,18+,20-,21-,22-/m0/s1
• InChI Key: MYLAQALEHHPXFU-LEQPGOCWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₁₁
• Molecular Weight: 468.40 g/mol
• Exact Mass: 468.16316171 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -1.01
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7409	74.09%
Caco-2	-	0.8960	89.60%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6015	60.15%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.7934	79.34%
OATP1B3 inhibitior	+	0.9542	95.42%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7053	70.53%
P-glycoprotein inhibitior	-	0.7396	73.96%
P-glycoprotein substrate	-	0.6581	65.81%
CYP3A4 substrate	+	0.6822	68.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.8782	87.82%
CYP2C9 inhibition	-	0.9337	93.37%
CYP2C19 inhibition	-	0.8881	88.81%
CYP2D6 inhibition	-	0.9009	90.09%
CYP1A2 inhibition	-	0.8801	88.01%
CYP2C8 inhibition	+	0.6839	68.39%
CYP inhibitory promiscuity	-	0.8383	83.83%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5340	53.40%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9663	96.63%
Skin irritation	-	0.7530	75.30%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4558	45.58%
Micronuclear	-	0.5626	56.26%
Hepatotoxicity	-	0.8223	82.23%
skin sensitisation	-	0.8358	83.58%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5839	58.39%
Acute Oral Toxicity (c)	III	0.5444	54.44%
Estrogen receptor binding	+	0.7419	74.19%
Androgen receptor binding	-	0.5126	51.26%
Thyroid receptor binding	+	0.6469	64.69%
Glucocorticoid receptor binding	+	0.5963	59.63%
Aromatase binding	+	0.6539	65.39%
PPAR gamma	+	0.6910	69.10%
Honey bee toxicity	-	0.8015	80.15%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.8363	83.63%

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	97.62%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.11%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	92.70%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.55%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.95%	96.21%
CHEMBL4208	P20618	Proteasome component C5	89.97%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.47%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.00%	99.17%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	85.63%	94.97%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.58%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.25%	95.83%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.84%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.98%	93.10%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.71%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.60%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.71%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.11%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.97%	94.00%

Plants that contains it

• Dacrycarpus imbricatus
• Ephedra equisetina
• Equisetum hyemale
• Lobelia chinensis
• Plantago major
• Pterocarpus santalinus
• Vitex trifolia

Cross-Links

• PubChem: 6325359
• NPASS: NPC30315