(E,5R)-5-[(1R,5R,6Z,9E,13R,15R)-5-acetyloxy-10-chloro-6-(hydroxymethyl)-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid

Details

• Internal ID: c79a2cd5-bf2e-4a90-895a-13b415607502
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (E,5R)-5-[(1R,5R,6Z,9E,13R,15R)-5-acetyloxy-10-chloro-6-(hydroxymethyl)-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid
• SMILES (Canonical): CC(=CC(C1C2CC(O1)CCC(=CCC=C(C(CC(=O)O2)OC(=O)C)CO)Cl)O)CC(=O)O
• SMILES (Isomeric): C/C(=C\[C@H]([C@@H]1[C@H]2C[C@H](O1)CC/C(=C\C/C=C(\[C@@H](CC(=O)O2)OC(=O)C)/CO)/Cl)O)/CC(=O)O
• InChI: InChI=1S/C23H31ClO9/c1-13(9-21(28)29)8-18(27)23-20-10-17(32-23)7-6-16(24)5-3-4-15(12-25)19(31-14(2)26)11-22(30)33-20/h4-5,8,17-20,23,25,27H,3,6-7,9-12H2,1-2H3,(H,28,29)/b13-8+,15-4-,16-5+/t17-,18-,19-,20-,23-/m1/s1
• InChI Key: KQAVQMQEPIWDEG-DDLODHIKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₁ClO₉
• Molecular Weight: 486.90 g/mol
• Exact Mass: 486.1656603 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• (E,5R)-5-[(1R,5R,6Z,9E,13R,15R)-5-acetyloxy-10-chloro-6-(hydroxymethyl)-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9583	95.83%
Caco-2	-	0.8077	80.77%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7489	74.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8360	83.60%
OATP1B3 inhibitior	+	0.8874	88.74%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9068	90.68%
P-glycoprotein inhibitior	+	0.6528	65.28%
P-glycoprotein substrate	+	0.5590	55.90%
CYP3A4 substrate	+	0.6668	66.68%
CYP2C9 substrate	-	0.8082	80.82%
CYP2D6 substrate	-	0.8783	87.83%
CYP3A4 inhibition	-	0.6173	61.73%
CYP2C9 inhibition	-	0.8283	82.83%
CYP2C19 inhibition	-	0.8363	83.63%
CYP2D6 inhibition	-	0.8688	86.88%
CYP1A2 inhibition	-	0.6790	67.90%
CYP2C8 inhibition	+	0.6446	64.46%
CYP inhibitory promiscuity	-	0.8635	86.35%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8682	86.82%
Carcinogenicity (trinary)	Danger	0.5191	51.91%
Eye corrosion	-	0.9831	98.31%
Eye irritation	-	0.9364	93.64%
Skin irritation	-	0.6329	63.29%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5136	51.36%
Micronuclear	-	0.8326	83.26%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.7140	71.40%
Acute Oral Toxicity (c)	III	0.5927	59.27%
Estrogen receptor binding	+	0.7979	79.79%
Androgen receptor binding	-	0.5660	56.60%
Thyroid receptor binding	-	0.5824	58.24%
Glucocorticoid receptor binding	+	0.8043	80.43%
Aromatase binding	+	0.5618	56.18%
PPAR gamma	+	0.6029	60.29%
Honey bee toxicity	-	0.7657	76.57%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9555	95.55%

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	98.04%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.24%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.06%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.72%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.73%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.88%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	91.73%	89.34%
CHEMBL3401	O75469	Pregnane X receptor	90.94%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	90.87%	91.19%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	90.40%	85.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.68%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.80%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.60%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.53%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	81.99%	97.79%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.78%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.16%	94.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 15973727
• LOTUS: LTS0249654
• wikiData: Q105144441