(1R,4aR,6R,7R,7aS)-6-(3-hydroxybenzoyl)oxy-7-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 003eb7c3-ed8a-47b7-8ca0-9271feedb7a8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1R,4aR,6R,7R,7aS)-6-(3-hydroxybenzoyl)oxy-7-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=CC(=CC=C4)O
• SMILES (Isomeric): C[C@H]1[C@@H](C[C@@H]2[C@@H]1[C@H](OC=C2C(=O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)OC(=O)C4=CC(=CC=C4)O
• InChI: InChI=1S/C23H28O12/c1-9-14(33-21(31)10-3-2-4-11(25)5-10)6-12-13(20(29)30)8-32-22(16(9)12)35-23-19(28)18(27)17(26)15(7-24)34-23/h2-5,8-9,12,14-19,22-28H,6-7H2,1H3,(H,29,30)/t9-,12-,14+,15+,16+,17+,18-,19+,22+,23+/m0/s1
• InChI Key: BSMWQZICWPFTBG-WXPXRUNGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₁₂
• Molecular Weight: 496.50 g/mol
• Exact Mass: 496.15807632 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.67
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7589	75.89%
Caco-2	-	0.9104	91.04%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6846	68.46%
OATP2B1 inhibitior	-	0.8542	85.42%
OATP1B1 inhibitior	-	0.4285	42.85%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6980	69.80%
P-glycoprotein inhibitior	-	0.7272	72.72%
P-glycoprotein substrate	-	0.6036	60.36%
CYP3A4 substrate	+	0.6513	65.13%
CYP2C9 substrate	-	0.8013	80.13%
CYP2D6 substrate	-	0.8769	87.69%
CYP3A4 inhibition	-	0.9155	91.55%
CYP2C9 inhibition	-	0.7874	78.74%
CYP2C19 inhibition	-	0.8152	81.52%
CYP2D6 inhibition	-	0.9060	90.60%
CYP1A2 inhibition	-	0.7606	76.06%
CYP2C8 inhibition	+	0.7067	70.67%
CYP inhibitory promiscuity	-	0.6412	64.12%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6577	65.77%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9500	95.00%
Skin irritation	-	0.7421	74.21%
Skin corrosion	-	0.9431	94.31%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6710	67.10%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6690	66.90%
skin sensitisation	-	0.8434	84.34%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7709	77.09%
Acute Oral Toxicity (c)	III	0.4978	49.78%
Estrogen receptor binding	+	0.7836	78.36%
Androgen receptor binding	-	0.5063	50.63%
Thyroid receptor binding	-	0.5524	55.24%
Glucocorticoid receptor binding	+	0.5536	55.36%
Aromatase binding	-	0.5174	51.74%
PPAR gamma	+	0.6292	62.92%
Honey bee toxicity	-	0.8372	83.72%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9426	94.26%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.76%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.45%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.05%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.67%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.08%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.85%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.66%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.43%	89.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	88.14%	97.53%
CHEMBL3401	O75469	Pregnane X receptor	87.80%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	86.61%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.85%	96.95%
CHEMBL4208	P20618	Proteasome component C5	84.04%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.71%	99.23%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.42%	94.23%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.60%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	80.39%	91.19%
CHEMBL2535	P11166	Glucose transporter	80.32%	98.75%

Plants that contains it

• Swertia japonica

Cross-Links

• PubChem: 162881316
• LOTUS: LTS0001935
• wikiData: Q104945314