(2S)-N-[(2S)-1-[[(2S)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-[(3-bromo-4-hydroxyphenyl)methyl]-21-hydroxy-2-[(1S)-1-hydroxyethyl]-15-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]-2-[[(2R)-2,3-dihydroxypropanoyl]amino]-5-(4-hydroxyphenyl)pentanamide

Details

• Internal ID: 2ad5edb8-92b7-4efb-9c4e-347a4be928a6
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2S)-N-[(2S)-1-[[(2S)-1-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-[(3-bromo-4-hydroxyphenyl)methyl]-21-hydroxy-2-[(1S)-1-hydroxyethyl]-15-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]-2-[[(2R)-2,3-dihydroxypropanoyl]amino]-5-(4-hydroxyphenyl)pentanamide
• SMILES (Canonical): CC1C(C(=O)NC(C(=O)NC2CCC(N(C2=O)C(C(=O)N(C(C(=O)NC(C(=O)O1)C(C)C)CC3=CC(=C(C=C3)O)Br)C)C(C)O)O)CC4=CC=C(C=C4)O)NC(=O)C(C(C)C)NC(=O)C(C)NC(=O)C(CCCC5=CC=C(C=C5)O)NC(=O)C(CO)O
• SMILES (Isomeric): C[C@@H]1[C@@H](C(=O)N[C@H](C(=O)N[C@H]2CC[C@H](N(C2=O)[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)O1)C(C)C)CC3=CC(=C(C=C3)O)Br)C)[C@H](C)O)O)CC4=CC=C(C=C4)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCC5=CC=C(C=C5)O)NC(=O)[C@@H](CO)O
• InChI: InChI=1S/C59H80BrN9O18/c1-28(2)46(65-50(77)30(5)61-51(78)39(62-54(81)44(75)27-70)11-9-10-33-12-17-36(72)18-13-33)55(82)67-48-32(7)87-59(86)47(29(3)4)66-53(80)42(26-35-16-22-43(74)38(60)24-35)68(8)58(85)49(31(6)71)69-45(76)23-21-40(57(69)84)63-52(79)41(64-56(48)83)25-34-14-19-37(73)20-15-34/h12-20,22,24,28-32,39-42,44-49,70-76H,9-11,21,23,25-27H2,1-8H3,(H,61,78)(H,62,81)(H,63,79)(H,64,83)(H,65,77)(H,66,80)(H,67,82)/t30-,31-,32+,39-,40-,41-,42-,44+,45+,46-,47-,48-,49-/m0/s1
• InChI Key: MZYZCUCXNWCJKE-XBFYRACCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₈₀BrN₉O₁₈
• Molecular Weight: 1283.20 g/mol
• Exact Mass: 1281.48047 g/mol
• Topological Polar Surface Area (TPSA): 412.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): -1.08
• H-Bond Acceptor: 18
• H-Bond Donor: 14
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7339	73.39%
Caco-2	-	0.8640	86.40%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Nucleus	0.4662	46.62%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8211	82.11%
OATP1B3 inhibitior	+	0.9278	92.78%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9047	90.47%
P-glycoprotein inhibitior	+	0.7417	74.17%
P-glycoprotein substrate	+	0.8848	88.48%
CYP3A4 substrate	+	0.7461	74.61%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.8409	84.09%
CYP3A4 inhibition	-	0.8981	89.81%
CYP2C9 inhibition	-	0.8545	85.45%
CYP2C19 inhibition	-	0.8599	85.99%
CYP2D6 inhibition	-	0.8882	88.82%
CYP1A2 inhibition	-	0.8832	88.32%
CYP2C8 inhibition	+	0.7878	78.78%
CYP inhibitory promiscuity	-	0.9184	91.84%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.5772	57.72%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.8967	89.67%
Skin irritation	-	0.7852	78.52%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7152	71.52%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5840	58.40%
skin sensitisation	-	0.8669	86.69%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8084	80.84%
Acute Oral Toxicity (c)	III	0.6188	61.88%
Estrogen receptor binding	+	0.6768	67.68%
Androgen receptor binding	+	0.7522	75.22%
Thyroid receptor binding	+	0.7116	71.16%
Glucocorticoid receptor binding	+	0.7349	73.49%
Aromatase binding	+	0.6771	67.71%
PPAR gamma	+	0.8037	80.37%
Honey bee toxicity	-	0.6780	67.80%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.7507	75.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.92%	98.95%
CHEMBL4072	P07858	Cathepsin B	99.80%	93.67%
CHEMBL5103	Q969S8	Histone deacetylase 10	99.20%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.50%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.29%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.72%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.60%	83.82%
CHEMBL226	P30542	Adenosine A1 receptor	97.47%	95.93%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	96.71%	85.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.30%	99.17%
CHEMBL3837	P07711	Cathepsin L	96.01%	96.61%
CHEMBL2094135	Q96BI3	Gamma-secretase	95.94%	98.05%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	95.38%	92.88%
CHEMBL236	P41143	Delta opioid receptor	95.33%	99.35%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.13%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.21%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.02%	93.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.70%	96.38%
CHEMBL4588	P22894	Matrix metalloproteinase 8	93.60%	94.66%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.05%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.75%	95.89%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	92.14%	97.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.35%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	90.91%	90.93%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.72%	93.00%
CHEMBL1937	Q92769	Histone deacetylase 2	90.47%	94.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.27%	90.71%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	90.12%	100.00%
CHEMBL255	P29275	Adenosine A2b receptor	89.92%	98.59%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	89.75%	95.34%
CHEMBL333	P08253	Matrix metalloproteinase-2	89.64%	96.31%
CHEMBL340	P08684	Cytochrome P450 3A4	89.43%	91.19%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.38%	97.14%
CHEMBL1949	P62937	Cyclophilin A	89.26%	98.57%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	89.23%	96.90%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	88.82%	82.38%
CHEMBL2514	O95665	Neurotensin receptor 2	88.58%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	88.52%	89.67%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.44%	99.15%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.97%	93.03%
CHEMBL2000	P03952	Plasma kallikrein	86.75%	93.92%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	86.70%	96.37%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.84%	89.50%
CHEMBL283	P08254	Matrix metalloproteinase 3	84.57%	97.29%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.55%	88.56%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	84.26%	97.64%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	84.14%	95.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.82%	100.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.67%	100.00%
CHEMBL3776	Q14790	Caspase-8	81.55%	97.06%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.70%	91.24%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.48%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139586661
• LOTUS: LTS0076076
• wikiData: Q77511536