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

Details

• Internal ID: 5ad14cd9-1a79-44cd-a293-61d95ef168f6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: 4a-hydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-7-carbaldehyde
• InChI: InChI=1S/C15H20O9/c16-5-7-1-2-15(21)3-4-22-13(9(7)15)24-14-12(20)11(19)10(18)8(6-17)23-14/h1,3-5,8-14,17-21H,2,6H2
• InChI Key: CZLZOXCIBSFIKX-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₉
• Molecular Weight: 344.31 g/mol
• Exact Mass: 344.11073221 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -2.45
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6240	62.40%
Caco-2	-	0.8672	86.72%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6436	64.36%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.8789	87.89%
OATP1B3 inhibitior	+	0.9483	94.83%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9532	95.32%
P-glycoprotein inhibitior	-	0.8860	88.60%
P-glycoprotein substrate	-	0.8689	86.89%
CYP3A4 substrate	+	0.5884	58.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8570	85.70%
CYP3A4 inhibition	-	0.9325	93.25%
CYP2C9 inhibition	-	0.9113	91.13%
CYP2C19 inhibition	-	0.8593	85.93%
CYP2D6 inhibition	-	0.8843	88.43%
CYP1A2 inhibition	-	0.8944	89.44%
CYP2C8 inhibition	-	0.7545	75.45%
CYP inhibitory promiscuity	-	0.8645	86.45%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6682	66.82%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9545	95.45%
Skin irritation	-	0.7411	74.11%
Skin corrosion	-	0.9466	94.66%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5668	56.68%
Micronuclear	-	0.6741	67.41%
Hepatotoxicity	-	0.8444	84.44%
skin sensitisation	-	0.8490	84.90%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5515	55.15%
Acute Oral Toxicity (c)	III	0.3819	38.19%
Estrogen receptor binding	-	0.7290	72.90%
Androgen receptor binding	-	0.5588	55.88%
Thyroid receptor binding	-	0.5583	55.83%
Glucocorticoid receptor binding	-	0.5080	50.80%
Aromatase binding	+	0.5712	57.12%
PPAR gamma	+	0.6095	60.95%
Honey bee toxicity	-	0.7441	74.41%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.7155	71.55%
Fish aquatic toxicity	-	0.5321	53.21%

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	98.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.32%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.63%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	87.76%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.29%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.23%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.66%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.37%	95.56%
CHEMBL4208	P20618	Proteasome component C5	82.07%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	81.85%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.88%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.51%	86.92%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.03%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162821414
• LOTUS: LTS0022126
• wikiData: Q105266079