7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-5-one

Details

• Internal ID: 4df00d57-bddc-4642-b0b9-1a6dc08ba2af
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 7-methyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-5-one
• SMILES (Canonical): CC1=CC(=O)C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC1=CC(=O)C2C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C15H20O8/c1-6-4-8(17)7-2-3-21-14(10(6)7)23-15-13(20)12(19)11(18)9(5-16)22-15/h2-4,7,9-16,18-20H,5H2,1H3
• InChI Key: SHZMGEYUEFSGCM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₈
• Molecular Weight: 328.31 g/mol
• Exact Mass: 328.11581759 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: -1.60
• Atomic LogP (AlogP): -1.57
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6060	60.60%
Caco-2	-	0.8713	87.13%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7219	72.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8518	85.18%
OATP1B3 inhibitior	+	0.9651	96.51%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8683	86.83%
P-glycoprotein inhibitior	-	0.9001	90.01%
P-glycoprotein substrate	-	0.9073	90.73%
CYP3A4 substrate	+	0.5389	53.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8850	88.50%
CYP3A4 inhibition	-	0.9410	94.10%
CYP2C9 inhibition	-	0.9057	90.57%
CYP2C19 inhibition	-	0.8767	87.67%
CYP2D6 inhibition	-	0.9136	91.36%
CYP1A2 inhibition	-	0.8619	86.19%
CYP2C8 inhibition	-	0.8735	87.35%
CYP inhibitory promiscuity	-	0.6622	66.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6998	69.98%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9432	94.32%
Skin irritation	-	0.7830	78.30%
Skin corrosion	-	0.9564	95.64%
Ames mutagenesis	-	0.6291	62.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.6151	61.51%
Micronuclear	-	0.6941	69.41%
Hepatotoxicity	-	0.7342	73.42%
skin sensitisation	-	0.8840	88.40%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5341	53.41%
Acute Oral Toxicity (c)	III	0.4409	44.09%
Estrogen receptor binding	-	0.6726	67.26%
Androgen receptor binding	-	0.5391	53.91%
Thyroid receptor binding	-	0.5644	56.44%
Glucocorticoid receptor binding	-	0.4919	49.19%
Aromatase binding	-	0.6515	65.15%
PPAR gamma	-	0.5425	54.25%
Honey bee toxicity	-	0.8322	83.22%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7050	70.50%
Fish aquatic toxicity	-	0.4188	41.88%

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	93.73%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.45%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.07%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.91%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.90%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.53%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.05%	85.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.29%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.35%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.98%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.34%	99.17%

Plants that contains it

• Linaria japonica

Cross-Links

• PubChem: 162978451
• LOTUS: LTS0019338
• wikiData: Q105253478