methyl 2-[(1S,6S)-1,6-dihydroxy-4-oxocyclohex-2-en-1-yl]acetate

Details

• Internal ID: 4ce6fde2-f119-4464-bfa8-4961b210dbfb
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Cyclic ketones > Cyclohexenones
• IUPAC Name: methyl 2-[(1S,6S)-1,6-dihydroxy-4-oxocyclohex-2-en-1-yl]acetate
• SMILES (Canonical): COC(=O)CC1(C=CC(=O)CC1O)O
• SMILES (Isomeric): COC(=O)C[C@@]1(C=CC(=O)C[C@@H]1O)O
• InChI: InChI=1S/C9H12O5/c1-14-8(12)5-9(13)3-2-6(10)4-7(9)11/h2-3,7,11,13H,4-5H2,1H3/t7-,9+/m0/s1
• InChI Key: VNLGHFSUFFZLJJ-IONNQARKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂O₅
• Molecular Weight: 200.19 g/mol
• Exact Mass: 200.06847348 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.83
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9273	92.73%
Caco-2	-	0.7993	79.93%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8655	86.55%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9343	93.43%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9199	91.99%
P-glycoprotein inhibitior	-	0.9755	97.55%
P-glycoprotein substrate	-	0.7862	78.62%
CYP3A4 substrate	+	0.5326	53.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8694	86.94%
CYP3A4 inhibition	-	0.9396	93.96%
CYP2C9 inhibition	-	0.9538	95.38%
CYP2C19 inhibition	-	0.9223	92.23%
CYP2D6 inhibition	-	0.9424	94.24%
CYP1A2 inhibition	-	0.9519	95.19%
CYP2C8 inhibition	-	0.9609	96.09%
CYP inhibitory promiscuity	-	0.9938	99.38%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8475	84.75%
Carcinogenicity (trinary)	Non-required	0.6762	67.62%
Eye corrosion	-	0.9650	96.50%
Eye irritation	+	0.6868	68.68%
Skin irritation	-	0.6331	63.31%
Skin corrosion	-	0.9097	90.97%
Ames mutagenesis	-	0.8400	84.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6261	62.61%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	-	0.6014	60.14%
skin sensitisation	-	0.7241	72.41%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6360	63.60%
Acute Oral Toxicity (c)	III	0.5784	57.84%
Estrogen receptor binding	-	0.8385	83.85%
Androgen receptor binding	-	0.7414	74.14%
Thyroid receptor binding	-	0.7411	74.11%
Glucocorticoid receptor binding	-	0.6650	66.50%
Aromatase binding	-	0.9015	90.15%
PPAR gamma	-	0.7283	72.83%
Honey bee toxicity	-	0.9499	94.99%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8993	89.93%

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	97.43%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.78%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.59%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	91.85%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	88.92%	90.17%
CHEMBL4208	P20618	Proteasome component C5	85.67%	90.00%
CHEMBL2581	P07339	Cathepsin D	84.87%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.72%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	83.93%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.26%	95.56%

Plants that contains it

• Pseudogynoxys chenopodioides

Cross-Links

• PubChem: 14287060
• LOTUS: LTS0100903
• wikiData: Q105289699