[(1R,3R,4aS,5R,7S,7aS)-3,4a,5-trihydroxy-1-methoxy-7-methyl-1,3,4,5,6,7a-hexahydrocyclopenta[c]pyran-7-yl] acetate

Details

• Internal ID: ae284ae9-4f77-40c3-85e7-428c635c3e20
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: [(1R,3R,4aS,5R,7S,7aS)-3,4a,5-trihydroxy-1-methoxy-7-methyl-1,3,4,5,6,7a-hexahydrocyclopenta[c]pyran-7-yl] acetate
• SMILES (Canonical): CC(=O)OC1(CC(C2(C1C(OC(C2)O)OC)O)O)C
• SMILES (Isomeric): CC(=O)O[C@]1(C[C@H]([C@]2([C@@H]1[C@@H](O[C@H](C2)O)OC)O)O)C
• InChI: InChI=1S/C12H20O7/c1-6(13)19-11(2)4-7(14)12(16)5-8(15)18-10(17-3)9(11)12/h7-10,14-16H,4-5H2,1-3H3/t7-,8-,9-,10-,11+,12-/m1/s1
• InChI Key: GWGHMCJQYGRQOT-QSZMHOAKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₀O₇
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.12090297 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -0.87
• H-Bond Acceptor: 7
• 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	+	0.6364	63.64%
Caco-2	-	0.7023	70.23%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5526	55.26%
OATP2B1 inhibitior	-	0.8516	85.16%
OATP1B1 inhibitior	+	0.9284	92.84%
OATP1B3 inhibitior	+	0.9198	91.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9225	92.25%
P-glycoprotein inhibitior	-	0.9143	91.43%
P-glycoprotein substrate	-	0.8472	84.72%
CYP3A4 substrate	+	0.6207	62.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8737	87.37%
CYP3A4 inhibition	-	0.8474	84.74%
CYP2C9 inhibition	-	0.9333	93.33%
CYP2C19 inhibition	-	0.8922	89.22%
CYP2D6 inhibition	-	0.9440	94.40%
CYP1A2 inhibition	-	0.7808	78.08%
CYP2C8 inhibition	-	0.8728	87.28%
CYP inhibitory promiscuity	-	0.9855	98.55%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6318	63.18%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9474	94.74%
Skin irritation	-	0.6628	66.28%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6777	67.77%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5926	59.26%
skin sensitisation	-	0.8732	87.32%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7590	75.90%
Acute Oral Toxicity (c)	III	0.3399	33.99%
Estrogen receptor binding	+	0.5779	57.79%
Androgen receptor binding	-	0.5713	57.13%
Thyroid receptor binding	+	0.6442	64.42%
Glucocorticoid receptor binding	-	0.6238	62.38%
Aromatase binding	-	0.6312	63.12%
PPAR gamma	-	0.5500	55.00%
Honey bee toxicity	-	0.7854	78.54%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7255	72.55%
Fish aquatic toxicity	+	0.6599	65.99%

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	97.32%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.18%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.11%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.35%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.88%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.14%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.01%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.03%	96.77%
CHEMBL340	P08684	Cytochrome P450 3A4	82.91%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.70%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.29%	97.28%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.12%	91.24%

Plants that contains it

• Dryopteris fragrans

Cross-Links

• PubChem: 101084573
• LOTUS: LTS0174167
• wikiData: Q105219347