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

Details

• Internal ID: 0928b98e-26d1-4157-8d73-e8c0d36337d6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 4,7-dimethyl-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-4a,5,7-triol
• SMILES (Canonical): CC1=COC(C2C1(C(CC2(C)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): CC1=COC(C2C1(C(CC2(C)O)O)O)OC3C(C(C(C(O3)CO)O)O)O
• InChI: InChI=1S/C16H26O10/c1-6-5-24-14(12-15(2,22)3-8(18)16(6,12)23)26-13-11(21)10(20)9(19)7(4-17)25-13/h5,7-14,17-23H,3-4H2,1-2H3
• InChI Key: IPTRSKQQZMUJQM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₁₀
• Molecular Weight: 378.37 g/mol
• Exact Mass: 378.15259702 g/mol
• Topological Polar Surface Area (TPSA): 169.00 Ų
• XlogP: -3.40
• Atomic LogP (AlogP): -3.07
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5635	56.35%
Caco-2	-	0.8754	87.54%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5450	54.50%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.8794	87.94%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9190	91.90%
P-glycoprotein inhibitior	-	0.8736	87.36%
P-glycoprotein substrate	-	0.8744	87.44%
CYP3A4 substrate	+	0.5963	59.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8354	83.54%
CYP3A4 inhibition	-	0.8983	89.83%
CYP2C9 inhibition	-	0.8949	89.49%
CYP2C19 inhibition	-	0.8933	89.33%
CYP2D6 inhibition	-	0.9228	92.28%
CYP1A2 inhibition	-	0.8698	86.98%
CYP2C8 inhibition	-	0.7876	78.76%
CYP inhibitory promiscuity	-	0.8169	81.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6123	61.23%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9785	97.85%
Skin irritation	-	0.7128	71.28%
Skin corrosion	-	0.9465	94.65%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5681	56.81%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.8177	81.77%
skin sensitisation	-	0.8665	86.65%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6535	65.35%
Acute Oral Toxicity (c)	III	0.4235	42.35%
Estrogen receptor binding	-	0.5775	57.75%
Androgen receptor binding	+	0.5760	57.60%
Thyroid receptor binding	+	0.6107	61.07%
Glucocorticoid receptor binding	-	0.5992	59.92%
Aromatase binding	+	0.7027	70.27%
PPAR gamma	+	0.5929	59.29%
Honey bee toxicity	-	0.8959	89.59%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6850	68.50%
Fish aquatic toxicity	-	0.3656	36.56%

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	93.98%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.47%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.37%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.10%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.62%	100.00%
CHEMBL4208	P20618	Proteasome component C5	83.39%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.57%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	81.48%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.19%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.12%	95.89%

Plants that contains it

• Clinopodium vulgare subsp. vulgare
• Lamium amplexicaule

Cross-Links

• PubChem: 15560022
• LOTUS: LTS0182028
• wikiData: Q105117487