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

Details

• Internal ID: fa93fb39-c169-456a-894b-08e9c4a5da7f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl 7-formyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CC=C2C=O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=COC(C2C1CC=C2C=O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C17H22O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,4,6,8,10-14,16-17,19-22H,3,5H2,1H3
• InChI Key: UCJAYNRULZBAQJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₁₀
• Molecular Weight: 386.30 g/mol
• Exact Mass: 386.12129689 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.02
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4663	46.63%
Caco-2	-	0.8694	86.94%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6885	68.85%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.7249	72.49%
OATP1B3 inhibitior	+	0.9720	97.20%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8322	83.22%
P-glycoprotein inhibitior	-	0.8489	84.89%
P-glycoprotein substrate	-	0.7306	73.06%
CYP3A4 substrate	+	0.6047	60.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8668	86.68%
CYP3A4 inhibition	-	0.9257	92.57%
CYP2C9 inhibition	-	0.8764	87.64%
CYP2C19 inhibition	-	0.8738	87.38%
CYP2D6 inhibition	-	0.9216	92.16%
CYP1A2 inhibition	-	0.8968	89.68%
CYP2C8 inhibition	-	0.6200	62.00%
CYP inhibitory promiscuity	-	0.8032	80.32%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6664	66.64%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9619	96.19%
Skin irritation	-	0.7833	78.33%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.5737	57.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5081	50.81%
Micronuclear	-	0.5941	59.41%
Hepatotoxicity	-	0.7642	76.42%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.8057	80.57%
Acute Oral Toxicity (c)	III	0.4853	48.53%
Estrogen receptor binding	+	0.7074	70.74%
Androgen receptor binding	+	0.5312	53.12%
Thyroid receptor binding	-	0.5802	58.02%
Glucocorticoid receptor binding	-	0.5050	50.50%
Aromatase binding	-	0.5870	58.70%
PPAR gamma	-	0.5464	54.64%
Honey bee toxicity	-	0.8243	82.43%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	-	0.4893	48.93%

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	96.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.30%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.53%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.31%	99.17%
CHEMBL4208	P20618	Proteasome component C5	87.27%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.40%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.43%	97.09%
CHEMBL5028	O14672	ADAM10	82.36%	97.50%
CHEMBL2581	P07339	Cathepsin D	82.01%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	80.06%	91.19%

Plants that contains it

• Cerbera manghas

Cross-Links

• PubChem: 14635618
• LOTUS: LTS0141918
• wikiData: Q105269939