[(3S,4R,5R)-5-[[(2R,3S,4S,5R,6R)-6-[(R)-cyano(phenyl)methoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4-dihydroxyoxolan-3-yl]methyl (1R,4aR,7aR)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(2-methoxybenzoyl)oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: e4e59a85-c90d-4d14-affd-496cafcc8ebe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(3S,4R,5R)-5-[[(2R,3S,4S,5R,6R)-6-[(R)-cyano(phenyl)methoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-3,4-dihydroxyoxolan-3-yl]methyl (1R,4aR,7aR)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(2-methoxybenzoyl)oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC1=CC=CC=C1C(=O)OCC2C(C(C(C(O2)OC3C4C(CC=C4CO)C(=CO3)C(=O)OCC5(COC(C5O)OCC6C(C(C(C(O6)OC(C#N)C7=CC=CC=C7)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC=CC=C1C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@H]3[C@@H]4[C@@H](CC=C4CO)C(=CO3)C(=O)OC[C@]5(CO[C@H]([C@@H]5O)OC[C@@H]6[C@H]([C@@H]([C@H]([C@@H](O6)O[C@@H](C#N)C7=CC=CC=C7)O)O)O)O)O)O)O
• InChI: InChI=1S/C43H51NO21/c1-56-25-10-6-5-9-23(25)37(53)57-16-27-30(46)33(49)35(51)41(64-27)65-39-29-21(14-45)11-12-22(29)24(15-58-39)38(54)60-18-43(55)19-61-42(36(43)52)59-17-28-31(47)32(48)34(50)40(63-28)62-26(13-44)20-7-3-2-4-8-20/h2-11,15,22,26-36,39-42,45-52,55H,12,14,16-19H2,1H3/t22-,26-,27+,28+,29-,30+,31+,32-,33-,34+,35+,36-,39+,40+,41-,42+,43+/m0/s1
• InChI Key: RXDKUDGWPCFXLG-GMEIGNFQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₅₁NO₂₁
• Molecular Weight: 917.90 g/mol
• Exact Mass: 917.29535764 g/mol
• Topological Polar Surface Area (TPSA): 332.00 Ų
• XlogP: -3.10
• Atomic LogP (AlogP): -2.43
• H-Bond Acceptor: 22
• H-Bond Donor: 9
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7096	70.96%
Caco-2	-	0.8693	86.93%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6097	60.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8307	83.07%
OATP1B3 inhibitior	+	0.9634	96.34%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9516	95.16%
P-glycoprotein inhibitior	+	0.7383	73.83%
P-glycoprotein substrate	+	0.7037	70.37%
CYP3A4 substrate	+	0.7282	72.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8489	84.89%
CYP3A4 inhibition	-	0.8990	89.90%
CYP2C9 inhibition	-	0.8278	82.78%
CYP2C19 inhibition	-	0.7609	76.09%
CYP2D6 inhibition	-	0.8748	87.48%
CYP1A2 inhibition	-	0.7829	78.29%
CYP2C8 inhibition	+	0.7806	78.06%
CYP inhibitory promiscuity	-	0.7729	77.29%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5695	56.95%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9039	90.39%
Skin irritation	-	0.7853	78.53%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8307	83.07%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8003	80.03%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6465	64.65%
Acute Oral Toxicity (c)	III	0.5049	50.49%
Estrogen receptor binding	+	0.8040	80.40%
Androgen receptor binding	+	0.7022	70.22%
Thyroid receptor binding	+	0.5930	59.30%
Glucocorticoid receptor binding	+	0.7137	71.37%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7831	78.31%
Honey bee toxicity	-	0.6251	62.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	0.9239	92.39%

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	97.95%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.83%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	94.68%	94.08%
CHEMBL2581	P07339	Cathepsin D	94.37%	98.95%
CHEMBL2535	P11166	Glucose transporter	93.50%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.43%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	93.27%	90.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.98%	97.36%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.88%	94.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.81%	89.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.38%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.20%	96.00%
CHEMBL5028	O14672	ADAM10	91.94%	97.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.75%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.51%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.78%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.67%	99.23%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.18%	83.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.57%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	85.86%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.13%	97.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.80%	95.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.21%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.92%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.87%	95.89%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.84%	96.67%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.52%	94.23%

Plants that contains it

• Psydrax schimperianus

Cross-Links

• PubChem: 162966566
• LOTUS: LTS0229253
• wikiData: Q105246946