methyl (3S,4R,5S,6S)-6-[(1S,2S,5S,6R)-2-chloro-5,6-dihydroxy-3-methoxycarbonylcyclohex-3-en-1-yl]oxy-3,4,5-trihydroxycyclohexene-1-carboxylate

Details

• Internal ID: fb55770c-75db-42dc-8bae-d4f9b7acb23a
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Shikimic acids and derivatves
• IUPAC Name: methyl (3S,4R,5S,6S)-6-[(1S,2S,5S,6R)-2-chloro-5,6-dihydroxy-3-methoxycarbonylcyclohex-3-en-1-yl]oxy-3,4,5-trihydroxycyclohexene-1-carboxylate
• SMILES (Canonical): COC(=O)C1=CC(C(C(C1OC2C(C(C=C(C2Cl)C(=O)OC)O)O)O)O)O
• SMILES (Isomeric): COC(=O)C1=C[C@@H]([C@H]([C@@H]([C@H]1O[C@H]2[C@@H]([C@H](C=C([C@@H]2Cl)C(=O)OC)O)O)O)O)O
• InChI: InChI=1S/C16H21ClO10/c1-25-15(23)5-3-8(19)11(21)14(9(5)17)27-13-6(16(24)26-2)4-7(18)10(20)12(13)22/h3-4,7-14,18-22H,1-2H3/t7-,8-,9-,10+,11+,12-,13-,14+/m0/s1
• InChI Key: ASEVULJAKVHVDT-ZOGIQTLHSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₁ClO₁₀
• Molecular Weight: 408.80 g/mol
• Exact Mass: 408.0823246 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: -2.70
• Atomic LogP (AlogP): -2.62
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8883	88.83%
Caco-2	-	0.8115	81.15%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8194	81.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8597	85.97%
OATP1B3 inhibitior	+	0.9277	92.77%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	-	0.8919	89.19%
P-glycoprotein inhibitior	-	0.7941	79.41%
P-glycoprotein substrate	-	0.8235	82.35%
CYP3A4 substrate	+	0.5476	54.76%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8644	86.44%
CYP3A4 inhibition	-	0.9355	93.55%
CYP2C9 inhibition	-	0.6808	68.08%
CYP2C19 inhibition	-	0.6508	65.08%
CYP2D6 inhibition	-	0.8022	80.22%
CYP1A2 inhibition	-	0.7854	78.54%
CYP2C8 inhibition	-	0.7819	78.19%
CYP inhibitory promiscuity	-	0.7810	78.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7515	75.15%
Carcinogenicity (trinary)	Danger	0.5237	52.37%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.9425	94.25%
Skin irritation	-	0.6466	64.66%
Skin corrosion	-	0.9181	91.81%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6194	61.94%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.6827	68.27%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.7936	79.36%
Acute Oral Toxicity (c)	III	0.4997	49.97%
Estrogen receptor binding	+	0.5378	53.78%
Androgen receptor binding	-	0.6201	62.01%
Thyroid receptor binding	+	0.5762	57.62%
Glucocorticoid receptor binding	-	0.5837	58.37%
Aromatase binding	-	0.6580	65.80%
PPAR gamma	-	0.4863	48.63%
Honey bee toxicity	-	0.6567	65.67%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9832	98.32%

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	95.43%	96.09%
CHEMBL4208	P20618	Proteasome component C5	87.68%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.17%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.24%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	82.93%	90.17%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.44%	81.11%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162920006
• LOTUS: LTS0131977
• wikiData: Q104917784