methyl (1S,4aS,6S,7R,7aR)-6-[(2R,3S,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate

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Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	b96cb2d9-75fe-43cd-b887-201bc0252420
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
IUPAC Name	methyl (1S,4aS,6S,7R,7aR)-6-[(2R,3S,4S)-3-ethenyl-4-(2-oxoethyl)-2-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbonyl]oxy-7-methyl-1-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
SMILES (Canonical)	CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C4=COC(C(C4CC=O)C=C)OC5C(C(C(C(O5)CO)O)O)O
SMILES (Isomeric)	C[C@H]1[C@H](C[C@H]2[C@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)O)OC(=O)C4=CO[C@@H]([C@H]([C@@H]4CC=O)C=C)O[C@H]5[C@H]([C@@H]([C@H]([C@H](O5)CO)O)O)O
InChI	InChI=1S/C33H46O19/c1-4-13-14(5-6-34)16(10-46-30(13)51-32-26(41)24(39)22(37)19(8-35)49-32)29(44)48-18-7-15-17(28(43)45-3)11-47-31(21(15)12(18)2)52-33-27(42)25(40)23(38)20(9-36)50-33/h4,6,10-15,18-27,30-33,35-42H,1,5,7-9H2,2-3H3/t12-,13-,14-,15+,18-,19+,20-,21-,22-,23-,24+,25+,26-,27-,30+,31-,32-,33-/m0/s1
InChI Key	GXXXVFMBJGIYPK-IGXCFTJJSA-N
Popularity	0 references in papers

Physical and Chemical Properties

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Molecular Formula	C₃₃H₄₆O₁₉
Molecular Weight	746.70 g/mol
Exact Mass	746.26332923 g/mol
Topological Polar Surface Area (TPSA)	287.00 Å²
XlogP	-2.50
Atomic LogP (AlogP)	-3.54
H-Bond Acceptor	19
H-Bond Donor	8
Rotatable Bonds	12

Synonyms

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There are no found synonyms.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5160	51.60%
Caco-2	-	0.8829	88.29%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6476	64.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3305	33.05%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6793	67.93%
P-glycoprotein inhibitior	+	0.6457	64.57%
P-glycoprotein substrate	+	0.5328	53.28%
CYP3A4 substrate	+	0.6905	69.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8825	88.25%
CYP3A4 inhibition	-	0.8611	86.11%
CYP2C9 inhibition	-	0.8933	89.33%
CYP2C19 inhibition	-	0.8599	85.99%
CYP2D6 inhibition	-	0.9209	92.09%
CYP1A2 inhibition	-	0.8938	89.38%
CYP2C8 inhibition	+	0.6455	64.55%
CYP inhibitory promiscuity	-	0.8615	86.15%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7398	73.98%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9180	91.80%
Skin irritation	-	0.7470	74.70%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	+	0.5446	54.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.7986	79.86%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8524	85.24%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5465	54.65%
Acute Oral Toxicity (c)	III	0.5174	51.74%
Estrogen receptor binding	+	0.8000	80.00%
Androgen receptor binding	+	0.6467	64.67%
Thyroid receptor binding	-	0.5096	50.96%
Glucocorticoid receptor binding	+	0.6052	60.52%
Aromatase binding	-	0.5266	52.66%
PPAR gamma	+	0.6756	67.56%
Honey bee toxicity	-	0.7355	73.55%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8221	82.21%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.98%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.66%	91.11%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.38%	86.92%
CHEMBL4208	P20618	Proteasome component C5	90.23%	90.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.80%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	87.79%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.78%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.40%	97.09%
CHEMBL5028	O14672	ADAM10	85.82%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.37%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.09%	95.83%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.30%	86.33%
CHEMBL2581	P07339	Cathepsin D	81.80%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	80.36%	91.19%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.