(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 6daea9a9-e0af-451e-860b-e324930db629
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): COC1C(C(C(C(O1)OC2C3C(CC=C3CO)C(=CO2)C(=O)O)O)O)O
• SMILES (Isomeric): CO[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H]3[C@H](CC=C3CO)C(=CO2)C(=O)O)O)O)O
• InChI: InChI=1S/C16H22O10/c1-23-15-11(19)10(18)12(20)16(26-15)25-14-9-6(4-17)2-3-7(9)8(5-24-14)13(21)22/h2,5,7,9-12,14-20H,3-4H2,1H3,(H,21,22)/t7-,9-,10+,11+,12-,14+,15+,16-/m1/s1
• InChI Key: VLHNUUYSBSLFOK-HCYRXJPGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₁₀
• Molecular Weight: 374.34 g/mol
• Exact Mass: 374.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -1.71
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6387	63.87%
Caco-2	-	0.8442	84.42%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7100	71.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8480	84.80%
OATP1B3 inhibitior	+	0.9654	96.54%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9058	90.58%
P-glycoprotein inhibitior	-	0.8907	89.07%
P-glycoprotein substrate	-	0.8308	83.08%
CYP3A4 substrate	+	0.5573	55.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8723	87.23%
CYP3A4 inhibition	-	0.8484	84.84%
CYP2C9 inhibition	-	0.8650	86.50%
CYP2C19 inhibition	-	0.7821	78.21%
CYP2D6 inhibition	-	0.8663	86.63%
CYP1A2 inhibition	-	0.7579	75.79%
CYP2C8 inhibition	-	0.7016	70.16%
CYP inhibitory promiscuity	-	0.5571	55.71%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6929	69.29%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.9450	94.50%
Skin irritation	-	0.7593	75.93%
Skin corrosion	-	0.9578	95.78%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7177	71.77%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6823	68.23%
skin sensitisation	-	0.8556	85.56%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6708	67.08%
Acute Oral Toxicity (c)	III	0.4519	45.19%
Estrogen receptor binding	-	0.6371	63.71%
Androgen receptor binding	+	0.5199	51.99%
Thyroid receptor binding	-	0.5130	51.30%
Glucocorticoid receptor binding	-	0.5936	59.36%
Aromatase binding	+	0.5282	52.82%
PPAR gamma	+	0.5221	52.21%
Honey bee toxicity	-	0.9048	90.48%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.8453	84.53%

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	96.78%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.09%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.24%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.05%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.92%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.81%	99.17%
CHEMBL5028	O14672	ADAM10	80.69%	97.50%
CHEMBL4208	P20618	Proteasome component C5	80.06%	90.00%

Plants that contains it

• Scyphiphora hydrophylacea

Cross-Links

• PubChem: 163191414
• LOTUS: LTS0058677
• wikiData: Q105288403