[(Z,2S,3R,4S,5R)-5-acetyloxy-3,4-dihydroxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate

Details

• Internal ID: 74007f37-50cb-41d9-aafc-c38ea4ae8e84
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(Z,2S,3R,4S,5R)-5-acetyloxy-3,4-dihydroxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate
• SMILES (Canonical): CC(C(C(C(C=CC1CC=CC(=O)O1)OC(=O)C)O)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]([C@@H]([C@@H]([C@@H](/C=C\[C@H]1CC=CC(=O)O1)OC(=O)C)O)O)OC(=O)C
• InChI: InChI=1S/C16H22O8/c1-9(22-10(2)17)15(20)16(21)13(23-11(3)18)8-7-12-5-4-6-14(19)24-12/h4,6-9,12-13,15-16,20-21H,5H2,1-3H3/b8-7-/t9-,12+,13+,15-,16+/m0/s1
• InChI Key: BBWWRLZIRMRLLC-KRSRSDIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₈
• Molecular Weight: 342.34 g/mol
• Exact Mass: 342.13146766 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.02
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6806	68.06%
Caco-2	-	0.5653	56.53%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7867	78.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9132	91.32%
OATP1B3 inhibitior	+	0.9512	95.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6575	65.75%
P-glycoprotein substrate	-	0.7719	77.19%
CYP3A4 substrate	+	0.5550	55.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8966	89.66%
CYP3A4 inhibition	-	0.8733	87.33%
CYP2C9 inhibition	-	0.9681	96.81%
CYP2C19 inhibition	-	0.9478	94.78%
CYP2D6 inhibition	-	0.9336	93.36%
CYP1A2 inhibition	-	0.9729	97.29%
CYP2C8 inhibition	-	0.8790	87.90%
CYP inhibitory promiscuity	-	0.9787	97.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8619	86.19%
Carcinogenicity (trinary)	Non-required	0.6214	62.14%
Eye corrosion	-	0.9225	92.25%
Eye irritation	-	0.9644	96.44%
Skin irritation	-	0.7007	70.07%
Skin corrosion	-	0.8950	89.50%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8009	80.09%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	+	0.5422	54.22%
skin sensitisation	-	0.8810	88.10%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.7111	71.11%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.6993	69.93%
Acute Oral Toxicity (c)	III	0.4987	49.87%
Estrogen receptor binding	-	0.5303	53.03%
Androgen receptor binding	-	0.7523	75.23%
Thyroid receptor binding	-	0.5602	56.02%
Glucocorticoid receptor binding	-	0.5987	59.87%
Aromatase binding	-	0.7000	70.00%
PPAR gamma	-	0.6774	67.74%
Honey bee toxicity	-	0.8070	80.70%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.5290	52.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.41%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.08%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.63%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.35%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.10%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.15%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.51%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.33%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.56%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.28%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.26%	96.77%

Plants that contains it

• Syncolostemon rotundifolius

Cross-Links

• PubChem: 13889717
• LOTUS: LTS0160637
• wikiData: Q104923116