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

Details

• Internal ID: d69166aa-7adb-4fcd-a820-14d8757e6edd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: [(1S,4aR,6S,7R,7aR)-4-formyl-4a-hydroxy-7-methyl-1-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-6-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(CC2(C1C(OC=C2C=O)OC3C(C(C(C(O3)CO)O)O)O)O)OC(=O)C=CC4=CC=C(C=C4)O
• SMILES (Isomeric): C[C@H]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
• InChI: InChI=1S/C25H30O12/c1-12-16(35-18(29)7-4-13-2-5-15(28)6-3-13)8-25(33)14(9-26)11-34-23(19(12)25)37-24-22(32)21(31)20(30)17(10-27)36-24/h2-7,9,11-12,16-17,19-24,27-28,30-33H,8,10H2,1H3/b7-4+/t12-,16-,17-,19-,20+,21+,22-,23-,24-,25-/m0/s1
• InChI Key: BEWQAFYRLCLDCO-GWRPGWMBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₂
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.17372639 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -1.04
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• 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	-	0.8988	89.88%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6368	63.68%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.7448	74.48%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8067	80.67%
P-glycoprotein inhibitior	-	0.5811	58.11%
P-glycoprotein substrate	-	0.5208	52.08%
CYP3A4 substrate	+	0.6835	68.35%
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	+	0.6968	69.68%
CYP inhibitory promiscuity	-	0.8253	82.53%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6103	61.03%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9535	95.35%
Skin irritation	-	0.6924	69.24%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4268	42.68%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.8194	81.94%
skin sensitisation	-	0.8308	83.08%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7326	73.26%
Acute Oral Toxicity (c)	III	0.4188	41.88%
Estrogen receptor binding	+	0.7824	78.24%
Androgen receptor binding	+	0.6376	63.76%
Thyroid receptor binding	+	0.5544	55.44%
Glucocorticoid receptor binding	+	0.6316	63.16%
Aromatase binding	+	0.5456	54.56%
PPAR gamma	+	0.6671	66.71%
Honey bee toxicity	-	0.7696	76.96%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
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	97.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.91%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.58%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.77%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.55%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.30%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.84%	96.00%
CHEMBL4208	P20618	Proteasome component C5	87.79%	90.00%
CHEMBL2581	P07339	Cathepsin D	87.00%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.02%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.92%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.76%	100.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.72%	85.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.32%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.23%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.72%	99.17%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.22%	94.23%

Plants that contains it

• Tecomaria capensis

Cross-Links

• PubChem: 162883369
• LOTUS: LTS0237057
• wikiData: Q104933663