[(1S,4S,5R,6S)-5-benzoyloxy-1,4,6-trihydroxycyclohex-2-en-1-yl]methyl benzoate

Details

• Internal ID: c870dac9-c18d-4362-bc8c-fa54992118f5
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters
• IUPAC Name: [(1S,4S,5R,6S)-5-benzoyloxy-1,4,6-trihydroxycyclohex-2-en-1-yl]methyl benzoate
• SMILES (Canonical): C1=CC=C(C=C1)C(=O)OCC2(C=CC(C(C2O)OC(=O)C3=CC=CC=C3)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C(=O)OC[C@]2(C=C[C@@H]([C@H]([C@@H]2O)OC(=O)C3=CC=CC=C3)O)O
• InChI: InChI=1S/C21H20O7/c22-16-11-12-21(26,13-27-19(24)14-7-3-1-4-8-14)18(23)17(16)28-20(25)15-9-5-2-6-10-15/h1-12,16-18,22-23,26H,13H2/t16-,17+,18-,21-/m0/s1
• InChI Key: PFCBOFJOXAUYRA-NYUBLWNDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₇
• Molecular Weight: 384.40 g/mol
• Exact Mass: 384.12090297 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7854	78.54%
Caco-2	-	0.8058	80.58%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8223	82.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9286	92.86%
OATP1B3 inhibitior	+	0.9230	92.30%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6838	68.38%
BSEP inhibitior	-	0.7081	70.81%
P-glycoprotein inhibitior	-	0.6844	68.44%
P-glycoprotein substrate	-	0.9093	90.93%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.5981	59.81%
CYP2D6 substrate	-	0.8266	82.66%
CYP3A4 inhibition	-	0.9335	93.35%
CYP2C9 inhibition	-	0.8919	89.19%
CYP2C19 inhibition	-	0.9132	91.32%
CYP2D6 inhibition	-	0.9400	94.00%
CYP1A2 inhibition	-	0.8881	88.81%
CYP2C8 inhibition	-	0.5907	59.07%
CYP inhibitory promiscuity	-	0.9486	94.86%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8832	88.32%
Carcinogenicity (trinary)	Non-required	0.6978	69.78%
Eye corrosion	-	0.9955	99.55%
Eye irritation	-	0.8949	89.49%
Skin irritation	-	0.8068	80.68%
Skin corrosion	-	0.9552	95.52%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6405	64.05%
Micronuclear	+	0.5851	58.51%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.6383	63.83%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.7523	75.23%
Acute Oral Toxicity (c)	III	0.7708	77.08%
Estrogen receptor binding	+	0.7060	70.60%
Androgen receptor binding	-	0.5703	57.03%
Thyroid receptor binding	-	0.6444	64.44%
Glucocorticoid receptor binding	+	0.5497	54.97%
Aromatase binding	-	0.5067	50.67%
PPAR gamma	+	0.5846	58.46%
Honey bee toxicity	-	0.8411	84.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9695	96.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.40%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.04%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.59%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.73%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.40%	94.62%
CHEMBL5028	O14672	ADAM10	84.69%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.19%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.17%	99.23%
CHEMBL3891	P07384	Calpain 1	80.74%	93.04%
CHEMBL4208	P20618	Proteasome component C5	80.52%	90.00%

Plants that contains it

• Monanthotaxis buchananii

Cross-Links

• PubChem: 14186981
• LOTUS: LTS0116414
• wikiData: Q105207622