methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: 1a1fd012-07cc-4485-ac22-c79533a58309
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aR,6S,7R,7aS)-4a,7-dihydroxy-6-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-7-methyl-1-[(2S,3S,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): CC1(C(CC2(C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C=CC4=CC=C(C=C4)OC)O
• SMILES (Isomeric): C[C@@]1([C@H](C[C@]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)O)OC(=O)/C=C/C4=CC=C(C=C4)OC)O
• InChI: InChI=1S/C27H34O14/c1-26(34)17(40-18(29)9-6-13-4-7-14(36-2)8-5-13)10-27(35)15(23(33)37-3)12-38-25(22(26)27)41-24-21(32)20(31)19(30)16(11-28)39-24/h4-9,12,16-17,19-22,24-25,28,30-32,34-35H,10-11H2,1-3H3/b9-6+/t16-,17-,19+,20-,21-,22+,24-,25-,26-,27-/m0/s1
• InChI Key: DVQVHBAATHWQAS-FZQVZOQKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₄
• Molecular Weight: 582.50 g/mol
• Exact Mass: 582.19485575 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -1.65
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8252	82.52%
Caco-2	-	0.8769	87.69%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.5192	51.92%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.8311	83.11%
OATP1B3 inhibitior	+	0.9206	92.06%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5925	59.25%
P-glycoprotein inhibitior	-	0.4481	44.81%
P-glycoprotein substrate	-	0.5688	56.88%
CYP3A4 substrate	+	0.6978	69.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8725	87.25%
CYP3A4 inhibition	-	0.8746	87.46%
CYP2C9 inhibition	-	0.8789	87.89%
CYP2C19 inhibition	-	0.8987	89.87%
CYP2D6 inhibition	-	0.9153	91.53%
CYP1A2 inhibition	-	0.8149	81.49%
CYP2C8 inhibition	+	0.6457	64.57%
CYP inhibitory promiscuity	-	0.8672	86.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6308	63.08%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9398	93.98%
Skin irritation	-	0.6932	69.32%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6615	66.15%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.7762	77.62%
skin sensitisation	-	0.8456	84.56%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8149	81.49%
Acute Oral Toxicity (c)	I	0.3838	38.38%
Estrogen receptor binding	+	0.7651	76.51%
Androgen receptor binding	+	0.6604	66.04%
Thyroid receptor binding	+	0.5692	56.92%
Glucocorticoid receptor binding	+	0.6930	69.30%
Aromatase binding	+	0.5569	55.69%
PPAR gamma	+	0.6925	69.25%
Honey bee toxicity	-	0.7678	76.78%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8733	87.33%

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	99.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.03%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.58%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.93%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.05%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.92%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	89.45%	90.17%
CHEMBL4208	P20618	Proteasome component C5	89.13%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.46%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.97%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.91%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.29%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.51%	97.28%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.27%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.47%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.02%	92.62%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.30%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.80%	94.33%
CHEMBL3401	O75469	Pregnane X receptor	80.57%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.33%	86.92%

Plants that contains it

• Bouchea pseudogervao
• Citharexylum spinosum

Cross-Links

• PubChem: 154496503
• LOTUS: LTS0037486
• wikiData: Q104990295