Methyl 7-(hydroxymethyl)-5-methoxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Details

• Internal ID: e8ce08fd-b507-4c5a-9be5-8a4a0d43769a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 7-(hydroxymethyl)-5-methoxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC1C=C(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC)CO
• SMILES (Isomeric): COC1C=C(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC)CO
• InChI: InChI=1S/C18H26O11/c1-25-9-3-7(4-19)11-12(9)8(16(24)26-2)6-27-17(11)29-18-15(23)14(22)13(21)10(5-20)28-18/h3,6,9-15,17-23H,4-5H2,1-2H3
• InChI Key: XJZRHAMUBWIJEV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₆O₁₁
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.14751164 g/mol
• Topological Polar Surface Area (TPSA): 164.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -2.60
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5351	53.51%
Caco-2	-	0.8430	84.30%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6797	67.97%
OATP2B1 inhibitior	-	0.8624	86.24%
OATP1B1 inhibitior	+	0.7716	77.16%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8841	88.41%
P-glycoprotein inhibitior	-	0.8277	82.77%
P-glycoprotein substrate	-	0.7795	77.95%
CYP3A4 substrate	+	0.5909	59.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.9318	93.18%
CYP2C9 inhibition	-	0.9253	92.53%
CYP2C19 inhibition	-	0.8513	85.13%
CYP2D6 inhibition	-	0.9005	90.05%
CYP1A2 inhibition	-	0.9152	91.52%
CYP2C8 inhibition	-	0.6961	69.61%
CYP inhibitory promiscuity	-	0.7190	71.90%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7025	70.25%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9437	94.37%
Skin irritation	-	0.8009	80.09%
Skin corrosion	-	0.9580	95.80%
Ames mutagenesis	+	0.5263	52.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5205	52.05%
Micronuclear	-	0.7041	70.41%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8762	87.62%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.6570	65.70%
Acute Oral Toxicity (c)	III	0.5093	50.93%
Estrogen receptor binding	+	0.6366	63.66%
Androgen receptor binding	-	0.5178	51.78%
Thyroid receptor binding	-	0.5872	58.72%
Glucocorticoid receptor binding	-	0.5675	56.75%
Aromatase binding	-	0.5184	51.84%
PPAR gamma	-	0.6141	61.41%
Honey bee toxicity	-	0.8345	83.45%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	-	0.5778	57.78%

Targets

Proven Targets:

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	95.58%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.55%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.07%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.99%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.63%	86.92%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.27%	96.00%
CHEMBL2581	P07339	Cathepsin D	82.12%	98.95%

Plants that contains it

• Gardenia jasminoides
• Oldenlandia herbacea var. herbacea

Cross-Links

• PubChem: 162848639
• LOTUS: LTS0253023
• wikiData: Q105329358