(E,5R)-5-[(1S,5S,6E,9Z,11R,13S,15S)-5-acetyloxy-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid

Details

• Internal ID: 6848db7a-b278-484f-a235-c7eaec3002ca
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (E,5R)-5-[(1S,5S,6E,9Z,11R,13S,15S)-5-acetyloxy-10-chloro-11-hydroxy-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid
• SMILES (Canonical): CC1=CCC=C(C(CC2CC(C(O2)C(C=C(C)CC(=O)O)O)OC(=O)CC1OC(=O)C)O)Cl
• SMILES (Isomeric): C/C/1=C\C/C=C(/[C@@H](C[C@H]2C[C@@H]([C@@H](O2)[C@@H](/C=C(\C)/CC(=O)O)O)OC(=O)C[C@@H]1OC(=O)C)O)\Cl
• InChI: InChI=1S/C23H31ClO9/c1-12(8-21(28)29)7-18(27)23-20-10-15(32-23)9-17(26)16(24)6-4-5-13(2)19(31-14(3)25)11-22(30)33-20/h5-7,15,17-20,23,26-27H,4,8-11H2,1-3H3,(H,28,29)/b12-7+,13-5+,16-6-/t15-,17+,18+,19-,20-,23-/m0/s1
• InChI Key: DMHSKAXPWDBKAA-FYWQBYQOSA-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: 1.40
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 8
• 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	+	0.9809	98.09%
Caco-2	-	0.8137	81.37%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5653	56.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8399	83.99%
OATP1B3 inhibitior	+	0.8375	83.75%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8194	81.94%
P-glycoprotein inhibitior	+	0.6222	62.22%
P-glycoprotein substrate	+	0.5645	56.45%
CYP3A4 substrate	+	0.6714	67.14%
CYP2C9 substrate	-	0.8090	80.90%
CYP2D6 substrate	-	0.8785	87.85%
CYP3A4 inhibition	-	0.6852	68.52%
CYP2C9 inhibition	-	0.8297	82.97%
CYP2C19 inhibition	-	0.7743	77.43%
CYP2D6 inhibition	-	0.8905	89.05%
CYP1A2 inhibition	-	0.7441	74.41%
CYP2C8 inhibition	+	0.6194	61.94%
CYP inhibitory promiscuity	-	0.8521	85.21%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8201	82.01%
Carcinogenicity (trinary)	Danger	0.5502	55.02%
Eye corrosion	-	0.9817	98.17%
Eye irritation	-	0.9374	93.74%
Skin irritation	-	0.6146	61.46%
Skin corrosion	-	0.9152	91.52%
Ames mutagenesis	-	0.5854	58.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6342	63.42%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8142	81.42%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.6759	67.59%
Acute Oral Toxicity (c)	III	0.4471	44.71%
Estrogen receptor binding	+	0.7654	76.54%
Androgen receptor binding	-	0.6350	63.50%
Thyroid receptor binding	-	0.5261	52.61%
Glucocorticoid receptor binding	+	0.7897	78.97%
Aromatase binding	+	0.5631	56.31%
PPAR gamma	+	0.6631	66.31%
Honey bee toxicity	-	0.7039	70.39%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9827	98.27%

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	97.27%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.27%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.03%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	95.45%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.16%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.30%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.09%	85.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	89.06%	89.34%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	88.86%	85.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.19%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	85.48%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.26%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.68%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.73%	96.95%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	82.60%	92.29%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.27%	89.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.89%	93.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.17%	93.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.97%	97.21%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 100936922
• LOTUS: LTS0217363
• wikiData: Q104985098