methyl (1S,4aS,6S,7R,7aS)-6-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-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-4-carboxylate

Details

• Internal ID: 22aef02b-6286-4ffc-b186-73c6a40180b9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aS,6S,7R,7aS)-6-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-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-4-carboxylate
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC
• 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)/C=C/C4=CC(=C(C=C4)O)OC
• InChI: InChI=1S/C27H34O13/c1-12-17(38-20(30)7-5-13-4-6-16(29)18(8-13)35-2)9-14-15(25(34)36-3)11-37-26(21(12)14)40-27-24(33)23(32)22(31)19(10-28)39-27/h4-8,11-12,14,17,19,21-24,26-29,31-33H,9-10H2,1-3H3/b7-5+/t12-,14+,17-,19+,21+,22+,23-,24+,26-,27-/m0/s1
• InChI Key: XOWVMKHUWDJUHZ-JIPUIFKVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₃
• Molecular Weight: 566.50 g/mol
• Exact Mass: 566.19994113 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): -0.17
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7729	77.29%
Caco-2	-	0.8724	87.24%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.5204	52.04%
OATP2B1 inhibitior	-	0.8660	86.60%
OATP1B1 inhibitior	+	0.7395	73.95%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7200	72.00%
P-glycoprotein inhibitior	-	0.5253	52.53%
P-glycoprotein substrate	-	0.5109	51.09%
CYP3A4 substrate	+	0.6794	67.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.8875	88.75%
CYP2C9 inhibition	-	0.7885	78.85%
CYP2C19 inhibition	-	0.8026	80.26%
CYP2D6 inhibition	-	0.8881	88.81%
CYP1A2 inhibition	-	0.7296	72.96%
CYP2C8 inhibition	+	0.7867	78.67%
CYP inhibitory promiscuity	-	0.7140	71.40%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7169	71.69%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9421	94.21%
Skin irritation	-	0.7713	77.13%
Skin corrosion	-	0.9472	94.72%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7161	71.61%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.7539	75.39%
skin sensitisation	-	0.8456	84.56%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9016	90.16%
Acute Oral Toxicity (c)	III	0.4732	47.32%
Estrogen receptor binding	+	0.8144	81.44%
Androgen receptor binding	+	0.5858	58.58%
Thyroid receptor binding	+	0.5561	55.61%
Glucocorticoid receptor binding	+	0.6893	68.93%
Aromatase binding	-	0.6015	60.15%
PPAR gamma	+	0.7020	70.20%
Honey bee toxicity	-	0.7868	78.68%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9304	93.04%

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	99.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.05%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.83%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.54%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.54%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.33%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.11%	99.17%
CHEMBL4208	P20618	Proteasome component C5	91.42%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.07%	86.92%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.64%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.87%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.21%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.64%	95.83%
CHEMBL3194	P02766	Transthyretin	83.72%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.30%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.91%	96.95%
CHEMBL1951	P21397	Monoamine oxidase A	80.57%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	80.36%	83.82%
CHEMBL5255	O00206	Toll-like receptor 4	80.07%	92.50%

Plants that contains it

• Lonicera morrowii

Cross-Links

• PubChem: 101108233
• LOTUS: LTS0233289
• wikiData: Q105337979