(1R,3S)-1-[[(2S,3R,4S)-5-[[(1S,4aS,6S,7R,7aS)-4-methoxycarbonyl-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-6-yl]oxycarbonyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

Details

• Internal ID: 97f18288-498c-4c3a-9846-56aaea061b5a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1R,3S)-1-[[(2S,3R,4S)-5-[[(1S,4aS,6S,7R,7aS)-4-methoxycarbonyl-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-6-yl]oxycarbonyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]methyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• InChI: InChI=1S/C44H56N2O20/c1-4-17-19(9-25-31-21(10-26(45-25)38(55)56)18-7-5-6-8-24(18)46-31)22(14-60-41(17)65-43-36(53)34(51)32(49)28(12-47)63-43)40(58)62-27-11-20-23(39(57)59-3)15-61-42(30(20)16(27)2)66-44-37(54)35(52)33(50)29(13-48)64-44/h4-8,14-17,19-20,25-30,32-37,41-54H,1,9-13H2,2-3H3,(H,55,56)/t16-,17+,19-,20+,25+,26-,27-,28+,29+,30+,32+,33+,34-,35-,36+,37+,41-,42-,43-,44-/m0/s1
• InChI Key: OEIJDGAXADWLTR-OIIITUQVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₅₆N₂O₂₀
• Molecular Weight: 932.90 g/mol
• Exact Mass: 932.34264218 g/mol
• Topological Polar Surface Area (TPSA): 335.00 Ų
• XlogP: -3.00
• Atomic LogP (AlogP): -1.91
• H-Bond Acceptor: 20
• H-Bond Donor: 11
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7643	76.43%
Caco-2	-	0.8749	87.49%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Nucleus	0.5060	50.60%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.7288	72.88%
OATP1B3 inhibitior	+	0.9351	93.51%
MATE1 inhibitior	-	0.9620	96.20%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8741	87.41%
P-glycoprotein inhibitior	+	0.7300	73.00%
P-glycoprotein substrate	+	0.7307	73.07%
CYP3A4 substrate	+	0.7403	74.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8508	85.08%
CYP3A4 inhibition	-	0.8945	89.45%
CYP2C9 inhibition	-	0.8044	80.44%
CYP2C19 inhibition	-	0.8182	81.82%
CYP2D6 inhibition	-	0.8286	82.86%
CYP1A2 inhibition	-	0.7233	72.33%
CYP2C8 inhibition	+	0.8137	81.37%
CYP inhibitory promiscuity	-	0.8265	82.65%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6513	65.13%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9082	90.82%
Skin irritation	-	0.7675	76.75%
Skin corrosion	-	0.9318	93.18%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7481	74.81%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.6716	67.16%
skin sensitisation	-	0.8348	83.48%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.6592	65.92%
Acute Oral Toxicity (c)	III	0.5994	59.94%
Estrogen receptor binding	+	0.8397	83.97%
Androgen receptor binding	+	0.7199	71.99%
Thyroid receptor binding	+	0.5762	57.62%
Glucocorticoid receptor binding	+	0.6654	66.54%
Aromatase binding	+	0.5443	54.43%
PPAR gamma	+	0.7737	77.37%
Honey bee toxicity	-	0.6634	66.34%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8262	82.62%

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	99.28%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.66%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.75%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.43%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	90.12%	95.83%
CHEMBL220	P22303	Acetylcholinesterase	89.98%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.97%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.51%	94.08%
CHEMBL5028	O14672	ADAM10	89.46%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.03%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.90%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	88.23%	94.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.38%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	87.09%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.99%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.42%	99.23%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	84.07%	85.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.04%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.35%	94.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.09%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.98%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	80.67%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.51%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.36%	95.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163193175
• LOTUS: LTS0227040
• wikiData: Q104246763