[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-20-chloro-13,19,22-trihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl] carbamate

Details

• Internal ID: 3cfe8b9c-bd3d-47c4-86ba-916a39532aa5
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-20-chloro-13,19,22-trihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18(22),19-hexaen-9-yl] carbamate
• SMILES (Canonical): CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=C(C(=C2O)C1)O)Cl)C)OC)OC(=O)N)C)C)O)OC
• SMILES (Isomeric): C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=C(C(=C2O)C1)O)Cl)/C)OC)OC(=O)N)\C)C)O)OC
• InChI: InChI=1S/C28H39ClN2O8/c1-14-10-18-24(33)19(29)13-20(25(18)34)31-27(35)15(2)8-7-9-21(37-5)26(39-28(30)36)17(4)12-16(3)23(32)22(11-14)38-6/h7-9,12-14,16,21-23,26,32-34H,10-11H2,1-6H3,(H2,30,36)(H,31,35)/b9-7-,15-8+,17-12+/t14-,16+,21+,22+,23-,26+/m1/s1
• InChI Key: ZXJVPFOYHLXWJE-LVBRMASUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₉ClN₂O₈
• Molecular Weight: 567.10 g/mol
• Exact Mass: 566.2394939 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 4.21
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

• SCHEMBL13009113

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9089	90.89%
Caco-2	-	0.7799	77.99%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4879	48.79%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8673	86.73%
OATP1B3 inhibitior	+	0.9310	93.10%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9519	95.19%
P-glycoprotein inhibitior	+	0.8451	84.51%
P-glycoprotein substrate	+	0.8615	86.15%
CYP3A4 substrate	+	0.7211	72.11%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.8679	86.79%
CYP3A4 inhibition	-	0.8479	84.79%
CYP2C9 inhibition	-	0.7938	79.38%
CYP2C19 inhibition	-	0.7444	74.44%
CYP2D6 inhibition	-	0.8703	87.03%
CYP1A2 inhibition	-	0.7393	73.93%
CYP2C8 inhibition	+	0.6932	69.32%
CYP inhibitory promiscuity	-	0.9228	92.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7649	76.49%
Carcinogenicity (trinary)	Non-required	0.5078	50.78%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9379	93.79%
Skin irritation	-	0.7876	78.76%
Skin corrosion	-	0.9311	93.11%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5838	58.38%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8438	84.38%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.7919	79.19%
Acute Oral Toxicity (c)	III	0.6150	61.50%
Estrogen receptor binding	+	0.8042	80.42%
Androgen receptor binding	+	0.8213	82.13%
Thyroid receptor binding	+	0.6458	64.58%
Glucocorticoid receptor binding	+	0.8506	85.06%
Aromatase binding	+	0.6205	62.05%
PPAR gamma	+	0.7832	78.32%
Honey bee toxicity	-	0.6659	66.59%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5151	51.51%
Fish aquatic toxicity	+	0.9791	97.91%

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	99.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.28%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.20%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.08%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.28%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.15%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.73%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.54%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.43%	91.07%
CHEMBL2581	P07339	Cathepsin D	89.31%	98.95%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	89.21%	85.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.89%	92.94%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.71%	93.03%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.03%	96.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.92%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.72%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.69%	94.80%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.76%	95.89%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.53%	86.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.37%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	83.76%	90.17%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	83.52%	94.42%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	83.36%	85.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.91%	91.19%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.91%	97.21%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.89%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.60%	91.03%
CHEMBL4208	P20618	Proteasome component C5	82.48%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.27%	90.71%
CHEMBL2535	P11166	Glucose transporter	81.02%	98.75%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.89%	96.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	80.85%	92.68%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.48%	100.00%
CHEMBL3474	P14555	Phospholipase A2 group IIA	80.47%	94.05%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 24992054
• LOTUS: LTS0055836
• wikiData: Q105385569