(1R)-1alpha,7aalpha-Dihydroxy-7-(hydroxymethyl)-1,4aalpha,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester

Details

• Internal ID: a4d45e3e-4578-4a96-b645-0419a7e98dd5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: methyl (1R,4aR,7aR)-1,7a-dihydroxy-7-(hydroxymethyl)-4a,5-dihydro-1H-cyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2(C1CC=C2CO)O)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@]2([C@@H]1CC=C2CO)O)O
• InChI: InChI=1S/C11H14O6/c1-16-9(13)7-5-17-10(14)11(15)6(4-12)2-3-8(7)11/h2,5,8,10,12,14-15H,3-4H2,1H3/t8-,10-,11+/m1/s1
• InChI Key: COOBCXFBMBAPFW-IEBDPFPHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄O₆
• Molecular Weight: 242.22 g/mol
• Exact Mass: 242.07903816 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -0.94
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6864	68.64%
Caco-2	-	0.8886	88.86%
Blood Brain Barrier	-	0.6398	63.98%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7384	73.84%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.8953	89.53%
OATP1B3 inhibitior	+	0.9610	96.10%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9196	91.96%
P-glycoprotein inhibitior	-	0.9723	97.23%
P-glycoprotein substrate	-	0.8167	81.67%
CYP3A4 substrate	+	0.5758	57.58%
CYP2C9 substrate	-	0.7974	79.74%
CYP2D6 substrate	-	0.8529	85.29%
CYP3A4 inhibition	-	0.9604	96.04%
CYP2C9 inhibition	-	0.8732	87.32%
CYP2C19 inhibition	-	0.8051	80.51%
CYP2D6 inhibition	-	0.9167	91.67%
CYP1A2 inhibition	-	0.7514	75.14%
CYP2C8 inhibition	-	0.8694	86.94%
CYP inhibitory promiscuity	-	0.8228	82.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7030	70.30%
Eye corrosion	-	0.9827	98.27%
Eye irritation	-	0.7972	79.72%
Skin irritation	-	0.7529	75.29%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6775	67.75%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6285	62.85%
skin sensitisation	-	0.8526	85.26%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6285	62.85%
Acute Oral Toxicity (c)	III	0.4445	44.45%
Estrogen receptor binding	-	0.4949	49.49%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.5857	58.57%
Glucocorticoid receptor binding	+	0.6104	61.04%
Aromatase binding	+	0.5669	56.69%
PPAR gamma	-	0.6498	64.98%
Honey bee toxicity	-	0.8813	88.13%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.7885	78.85%

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	97.72%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.24%	91.11%
CHEMBL4208	P20618	Proteasome component C5	88.93%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.25%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.98%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.12%	96.95%

Plants that contains it

• Genipa americana

Cross-Links

• PubChem: 16655217
• LOTUS: LTS0086323
• wikiData: Q104967180