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

Details

• Internal ID: eb7dff35-97ed-4081-8f61-06abe36e6078
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,6S,7R,7aS)-4-formyl-4a,7-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-6-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1(C(CC2(C1C(OC=C2C=O)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C=CC4=CC=C(C=C4)O)O
• SMILES (Isomeric): C[C@@]1([C@H](C[C@]2([C@@H]1[C@@H](OC=C2C=O)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)O)O
• InChI: InChI=1S/C25H30O13/c1-24(33)16(37-17(29)7-4-12-2-5-14(28)6-3-12)8-25(34)13(9-26)11-35-23(21(24)25)38-22-20(32)19(31)18(30)15(10-27)36-22/h2-7,9,11,15-16,18-23,27-28,30-34H,8,10H2,1H3/b7-4+/t15-,16+,18-,19+,20-,21-,22+,23+,24+,25+/m1/s1
• InChI Key: XXQDVCJDTNXXPT-FMFKOEADSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₃
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.16864101 g/mol
• Topological Polar Surface Area (TPSA): 213.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.93
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8207	82.07%
Caco-2	-	0.9000	90.00%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Mitochondria	0.6368	63.68%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.7952	79.52%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7917	79.17%
P-glycoprotein inhibitior	-	0.5680	56.80%
P-glycoprotein substrate	-	0.5903	59.03%
CYP3A4 substrate	+	0.6808	68.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8748	87.48%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.8392	83.92%
CYP2C19 inhibition	-	0.8666	86.66%
CYP2D6 inhibition	-	0.9109	91.09%
CYP1A2 inhibition	-	0.8132	81.32%
CYP2C8 inhibition	+	0.7293	72.93%
CYP inhibitory promiscuity	-	0.8253	82.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6103	61.03%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9402	94.02%
Skin irritation	-	0.6924	69.24%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3653	36.53%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.8223	82.23%
skin sensitisation	-	0.8308	83.08%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6689	66.89%
Acute Oral Toxicity (c)	III	0.4188	41.88%
Estrogen receptor binding	+	0.8165	81.65%
Androgen receptor binding	+	0.6816	68.16%
Thyroid receptor binding	+	0.5392	53.92%
Glucocorticoid receptor binding	+	0.6276	62.76%
Aromatase binding	+	0.6170	61.70%
PPAR gamma	+	0.6652	66.52%
Honey bee toxicity	-	0.7922	79.22%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6355	63.55%
Fish aquatic toxicity	+	0.9137	91.37%

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	98.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.20%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.60%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.72%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.95%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.43%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.14%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.63%	94.45%
CHEMBL2581	P07339	Cathepsin D	86.56%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.92%	99.17%
CHEMBL206	P03372	Estrogen receptor alpha	83.89%	97.64%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.54%	89.67%
CHEMBL4208	P20618	Proteasome component C5	83.51%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.47%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.22%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.17%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.15%	97.28%

Plants that contains it

• Campsis grandiflora

Cross-Links

• PubChem: 21594946
• LOTUS: LTS0149246
• wikiData: Q105344155