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

Details

• Internal ID: cda1e344-f3d6-48d3-8d46-c81323fdd90b
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters
• IUPAC Name: [(1S,4R,5S,6S)-4-benzoyloxy-1,5,6-trihydroxycyclohex-2-en-1-yl]methyl benzoate
• SMILES (Canonical): C1=CC=C(C=C1)C(=O)OCC2(C=CC(C(C2O)O)OC(=O)C3=CC=CC=C3)O
• SMILES (Isomeric): C1=CC=C(C=C1)C(=O)OC[C@]2(C=C[C@H]([C@H]([C@@H]2O)O)OC(=O)C3=CC=CC=C3)O
• InChI: InChI=1S/C21H20O7/c22-17-16(28-20(25)15-9-5-2-6-10-15)11-12-21(26,18(17)23)13-27-19(24)14-7-3-1-4-8-14/h1-12,16-18,22-23,26H,13H2/t16-,17-,18+,21+/m1/s1
• InChI Key: PCFGXGDGOLIQTE-WIRSXHRWSA-N
• Popularity: 1 reference 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	+	0.6228	62.28%
Caco-2	-	0.8297	82.97%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8146	81.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9444	94.44%
OATP1B3 inhibitior	+	0.9440	94.40%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7588	75.88%
BSEP inhibitior	-	0.5620	56.20%
P-glycoprotein inhibitior	-	0.6994	69.94%
P-glycoprotein substrate	-	0.8963	89.63%
CYP3A4 substrate	-	0.5084	50.84%
CYP2C9 substrate	-	0.5981	59.81%
CYP2D6 substrate	-	0.8266	82.66%
CYP3A4 inhibition	-	0.9176	91.76%
CYP2C9 inhibition	-	0.8850	88.50%
CYP2C19 inhibition	-	0.9113	91.13%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.8889	88.89%
CYP2C8 inhibition	-	0.5578	55.78%
CYP inhibitory promiscuity	-	0.9382	93.82%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8932	89.32%
Carcinogenicity (trinary)	Non-required	0.6976	69.76%
Eye corrosion	-	0.9960	99.60%
Eye irritation	-	0.8835	88.35%
Skin irritation	-	0.8143	81.43%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4159	41.59%
Micronuclear	+	0.5651	56.51%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7136	71.36%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7465	74.65%
Acute Oral Toxicity (c)	III	0.7772	77.72%
Estrogen receptor binding	+	0.7906	79.06%
Androgen receptor binding	-	0.5429	54.29%
Thyroid receptor binding	-	0.5494	54.94%
Glucocorticoid receptor binding	+	0.6466	64.66%
Aromatase binding	-	0.4910	49.10%
PPAR gamma	+	0.5430	54.30%
Honey bee toxicity	-	0.8982	89.82%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5955	59.55%
Fish aquatic toxicity	+	0.9708	97.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	98.07%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.26%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.46%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.26%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.58%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.32%	95.56%
CHEMBL2535	P11166	Glucose transporter	85.30%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.99%	91.11%
CHEMBL5028	O14672	ADAM10	84.62%	97.50%

Plants that contains it

• Piper cubeba

Cross-Links

• PubChem: 14890284
• NPASS: NPC72775
• LOTUS: LTS0013677
• wikiData: Q105205691