1-[3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4,7-dicarboxylic acid

Details

• Internal ID: 62258b25-2f81-4c84-9e15-de09ea35c1c6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4,7-dicarboxylic acid
• InChI: InChI=1S/C16H22O11/c17-3-8-10(18)11(19)12(20)16(26-8)27-15-9-5(1-2-6(9)13(21)22)7(4-25-15)14(23)24/h4-6,8-12,15-20H,1-3H2,(H,21,22)(H,23,24)
• InChI Key: CBXLCEGPMWRVQS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34 g/mol
• Exact Mass: 390.11621151 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.15
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5691	56.91%
Caco-2	-	0.9135	91.35%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	0.7188	71.88%
OATP1B1 inhibitior	-	0.3184	31.84%
OATP1B3 inhibitior	+	0.9601	96.01%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9327	93.27%
P-glycoprotein inhibitior	-	0.9000	90.00%
P-glycoprotein substrate	-	0.9353	93.53%
CYP3A4 substrate	+	0.5258	52.58%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8715	87.15%
CYP3A4 inhibition	-	0.9221	92.21%
CYP2C9 inhibition	-	0.8472	84.72%
CYP2C19 inhibition	-	0.8726	87.26%
CYP2D6 inhibition	-	0.9007	90.07%
CYP1A2 inhibition	-	0.8532	85.32%
CYP2C8 inhibition	-	0.7100	71.00%
CYP inhibitory promiscuity	-	0.8618	86.18%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7039	70.39%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9031	90.31%
Skin irritation	-	0.7699	76.99%
Skin corrosion	-	0.9449	94.49%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6667	66.67%
Micronuclear	-	0.7141	71.41%
Hepatotoxicity	-	0.8339	83.39%
skin sensitisation	-	0.8813	88.13%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.5571	55.71%
Acute Oral Toxicity (c)	III	0.4193	41.93%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5772	57.72%
Thyroid receptor binding	-	0.6029	60.29%
Glucocorticoid receptor binding	-	0.7249	72.49%
Aromatase binding	-	0.5687	56.87%
PPAR gamma	-	0.4871	48.71%
Honey bee toxicity	-	0.8919	89.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	-	0.4560	45.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	93.88%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.61%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.58%	91.11%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.82%	94.23%
CHEMBL5255	O00206	Toll-like receptor 4	83.56%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.40%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.83%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.64%	93.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.10%	97.25%

Plants that contains it

• Forsythia viridissima

Cross-Links

• PubChem: 15559327
• LOTUS: LTS0212323
• wikiData: Q104952938