(1R,3S,6S,7E,13S,16R,17R,21S,22S)-17-[(2S,4S,5R,6S)-5-[(2R,4S,5S,6S)-4-(3-chloro-6-methoxy-2-methylbenzoyl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-28-hydroxy-3,22-dimethyl-23,26-dioxo-24,27-dioxapentacyclo[23.2.1.01,6.013,22.016,21]octacosa-4,7,14,25(28)-tetraene-4-carboxylic acid

Details

• Internal ID: 4727be8b-d4d4-47ef-a60e-fd04191a7399
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1R,3S,6S,7E,13S,16R,17R,21S,22S)-17-[(2S,4S,5R,6S)-5-[(2R,4S,5S,6S)-4-(3-chloro-6-methoxy-2-methylbenzoyl)oxy-5-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-28-hydroxy-3,22-dimethyl-23,26-dioxo-24,27-dioxapentacyclo[23.2.1.01,6.013,22.016,21]octacosa-4,7,14,25(28)-tetraene-4-carboxylic acid
• SMILES (Canonical): CC1CC23C(C=CCCCCC4C=CC5C(C4(C(=O)OC(=C2O)C(=O)O3)C)CCCC5OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC(=O)C8=C(C=CC(=C8C)Cl)OC)O)C=C1C(=O)O
• SMILES (Isomeric): C[C@H]1C[C@@]23[C@@H](/C=C/CCCC[C@H]4C=C[C@@H]5[C@@H]([C@]4(C(=O)OC(=C2O)C(=O)O3)C)CCC[C@H]5O[C@@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC(=O)C8=C(C=CC(=C8C)Cl)OC)O)C=C1C(=O)O
• InChI: InChI=1S/C50H63ClO16/c1-24-23-50-29(20-31(24)45(55)56)13-10-8-7-9-12-28-16-17-30-32(49(28,5)48(59)66-43(44(50)54)47(58)67-50)14-11-15-35(30)63-38-21-34(52)42(27(4)62-38)65-39-22-37(41(53)26(3)61-39)64-46(57)40-25(2)33(51)18-19-36(40)60-6/h10,13,16-20,24,26-30,32,34-35,37-39,41-42,52-54H,7-9,11-12,14-15,21-23H2,1-6H3,(H,55,56)/b13-10+/t24-,26-,27-,28-,29-,30+,32-,34-,35+,37-,38+,39+,41-,42-,49-,50+/m0/s1
• InChI Key: WUXHQHDSSKBJFH-ZYJIKBHJSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₆₃ClO₁₆
• Molecular Weight: 955.50 g/mol
• Exact Mass: 954.3804636 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: 7.50
• Atomic LogP (AlogP): 6.96
• H-Bond Acceptor: 15
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9920	99.20%
Caco-2	-	0.8626	86.26%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7721	77.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7916	79.16%
OATP1B3 inhibitior	+	0.8147	81.47%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6321	63.21%
BSEP inhibitior	+	0.9667	96.67%
P-glycoprotein inhibitior	+	0.7533	75.33%
P-glycoprotein substrate	+	0.7800	78.00%
CYP3A4 substrate	+	0.7590	75.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8730	87.30%
CYP3A4 inhibition	-	0.8719	87.19%
CYP2C9 inhibition	-	0.7372	73.72%
CYP2C19 inhibition	-	0.7815	78.15%
CYP2D6 inhibition	-	0.8578	85.78%
CYP1A2 inhibition	-	0.5489	54.89%
CYP2C8 inhibition	+	0.8149	81.49%
CYP inhibitory promiscuity	-	0.8214	82.14%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Danger	0.6143	61.43%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9041	90.41%
Skin irritation	-	0.6374	63.74%
Skin corrosion	-	0.9180	91.80%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6836	68.36%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8507	85.07%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7206	72.06%
Acute Oral Toxicity (c)	II	0.3366	33.66%
Estrogen receptor binding	+	0.8312	83.12%
Androgen receptor binding	+	0.7429	74.29%
Thyroid receptor binding	+	0.5869	58.69%
Glucocorticoid receptor binding	+	0.7466	74.66%
Aromatase binding	+	0.5796	57.96%
PPAR gamma	+	0.7895	78.95%
Honey bee toxicity	-	0.6508	65.08%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6104	61.04%
Fish aquatic toxicity	+	0.9974	99.74%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.27%	96.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	96.22%	83.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.47%	91.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	94.66%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.35%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.34%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.99%	94.45%
CHEMBL4208	P20618	Proteasome component C5	93.15%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.21%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.87%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	88.66%	91.19%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.13%	97.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.89%	94.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.42%	94.08%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.16%	92.62%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	83.78%	97.31%
CHEMBL220	P22303	Acetylcholinesterase	83.71%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	83.44%	90.17%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	83.18%	95.52%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.93%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.90%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.62%	92.50%
CHEMBL3401	O75469	Pregnane X receptor	81.77%	94.73%
CHEMBL2535	P11166	Glucose transporter	81.61%	98.75%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.52%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	81.06%	95.38%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.34%	93.03%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.26%	95.78%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 133562642
• LOTUS: LTS0092429
• wikiData: Q105313367