[(1R,4aR,7R,7aS)-1-acetyloxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-yl]methyl acetate

Details

• Internal ID: 0eb9e7f1-9ea4-4c0e-b9e9-171aa0825e3d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: [(1R,4aR,7R,7aS)-1-acetyloxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-yl]methyl acetate
• SMILES (Canonical): CC1CCC2C1C(OC=C2COC(=O)C)OC(=O)C
• SMILES (Isomeric): C[C@@H]1CC[C@@H]2[C@H]1[C@H](OC=C2COC(=O)C)OC(=O)C
• InChI: InChI=1S/C14H20O5/c1-8-4-5-12-11(6-17-9(2)15)7-18-14(13(8)12)19-10(3)16/h7-8,12-14H,4-6H2,1-3H3/t8-,12+,13+,14-/m1/s1
• InChI Key: PWSAKIKRNLLDNQ-DGJRKYIQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₀O₅
• Molecular Weight: 268.30 g/mol
• Exact Mass: 268.13107373 g/mol
• Topological Polar Surface Area (TPSA): 61.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.02
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9866	98.66%
Caco-2	+	0.7176	71.76%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6256	62.56%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.8877	88.77%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8458	84.58%
P-glycoprotein inhibitior	-	0.8595	85.95%
P-glycoprotein substrate	-	0.8597	85.97%
CYP3A4 substrate	+	0.5428	54.28%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8520	85.20%
CYP3A4 inhibition	-	0.7971	79.71%
CYP2C9 inhibition	-	0.7089	70.89%
CYP2C19 inhibition	-	0.7011	70.11%
CYP2D6 inhibition	-	0.8361	83.61%
CYP1A2 inhibition	+	0.6592	65.92%
CYP2C8 inhibition	-	0.6928	69.28%
CYP inhibitory promiscuity	-	0.7505	75.05%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7102	71.02%
Eye corrosion	-	0.9358	93.58%
Eye irritation	-	0.5858	58.58%
Skin irritation	-	0.6140	61.40%
Skin corrosion	-	0.9595	95.95%
Ames mutagenesis	-	0.5970	59.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4618	46.18%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.6235	62.35%
skin sensitisation	-	0.8183	81.83%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4797	47.97%
Acute Oral Toxicity (c)	III	0.6149	61.49%
Estrogen receptor binding	-	0.5801	58.01%
Androgen receptor binding	+	0.5314	53.14%
Thyroid receptor binding	-	0.6158	61.58%
Glucocorticoid receptor binding	+	0.5797	57.97%
Aromatase binding	-	0.7443	74.43%
PPAR gamma	-	0.6661	66.61%
Honey bee toxicity	-	0.9068	90.68%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6105	61.05%
Fish aquatic toxicity	+	0.9934	99.34%

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	97.26%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.00%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.71%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.42%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.90%	94.80%
CHEMBL2581	P07339	Cathepsin D	88.89%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.57%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.13%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.67%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.66%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.29%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.63%	95.89%

Plants that contains it

• Teucrium marum

Cross-Links

• PubChem: 162950363
• LOTUS: LTS0021360
• wikiData: Q105215965