(4S)-4-amino-5-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-8-[(2S)-butan-2-yl]-21-hydroxy-15-[(4-hydroxycyclohex-2-en-1-yl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-2-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-5-oxopentanoic acid

Details

• Internal ID: 983f3d9a-914f-4400-9da0-56bd5f59f4da
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (4S)-4-amino-5-[[(2S,5S,8S,11R,12S,15S,18S,21R)-5-benzyl-8-[(2S)-butan-2-yl]-21-hydroxy-15-[(4-hydroxycyclohex-2-en-1-yl)methyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-2-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docosan-12-yl]amino]-5-oxopentanoic acid
• SMILES (Canonical): CCC(C)C1C(=O)OC(C(C(=O)NC(C(=O)NC2CCC(N(C2=O)C(C(=O)N(C(C(=O)N1)CC3=CC=CC=C3)C)C(C)C)O)CC4CCC(C=C4)O)NC(=O)C(CCC(=O)O)N)C
• SMILES (Isomeric): CC[C@H](C)[C@H]1C(=O)O[C@@H]([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)N1)CC3=CC=CC=C3)C)C(C)C)O)CC4CCC(C=C4)O)NC(=O)[C@H](CCC(=O)O)N)C
• InChI: InChI=1S/C44H65N7O12/c1-7-24(4)35-44(62)63-25(5)36(49-38(56)29(45)17-20-34(54)55)41(59)47-31(21-27-13-15-28(52)16-14-27)39(57)46-30-18-19-33(53)51(42(30)60)37(23(2)3)43(61)50(6)32(40(58)48-35)22-26-11-9-8-10-12-26/h8-13,15,23-25,27-33,35-37,52-53H,7,14,16-22,45H2,1-6H3,(H,46,57)(H,47,59)(H,48,58)(H,49,56)(H,54,55)/t24-,25+,27?,28?,29-,30-,31-,32-,33+,35-,36-,37-/m0/s1
• InChI Key: ZITZTTGIHQISPA-QEXQDPFASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₅N₇O₁₂
• Molecular Weight: 884.00 g/mol
• Exact Mass: 883.46912053 g/mol
• Topological Polar Surface Area (TPSA): 287.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -0.14
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

• SCHEMBL29884744

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5914	59.14%
Caco-2	-	0.8755	87.55%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.3367	33.67%
OATP2B1 inhibitior	-	0.7144	71.44%
OATP1B1 inhibitior	+	0.8185	81.85%
OATP1B3 inhibitior	+	0.9246	92.46%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8890	88.90%
BSEP inhibitior	+	0.6179	61.79%
P-glycoprotein inhibitior	+	0.7412	74.12%
P-glycoprotein substrate	+	0.8595	85.95%
CYP3A4 substrate	+	0.7211	72.11%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8344	83.44%
CYP3A4 inhibition	+	0.6158	61.58%
CYP2C9 inhibition	-	0.9061	90.61%
CYP2C19 inhibition	-	0.8601	86.01%
CYP2D6 inhibition	-	0.8937	89.37%
CYP1A2 inhibition	-	0.9047	90.47%
CYP2C8 inhibition	+	0.7039	70.39%
CYP inhibitory promiscuity	-	0.9810	98.10%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5884	58.84%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9100	91.00%
Skin irritation	-	0.7760	77.60%
Skin corrosion	-	0.9192	91.92%
Ames mutagenesis	-	0.5382	53.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.4601	46.01%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5416	54.16%
skin sensitisation	-	0.8774	87.74%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.9038	90.38%
Acute Oral Toxicity (c)	III	0.6578	65.78%
Estrogen receptor binding	+	0.8350	83.50%
Androgen receptor binding	+	0.6589	65.89%
Thyroid receptor binding	+	0.5985	59.85%
Glucocorticoid receptor binding	+	0.6582	65.82%
Aromatase binding	+	0.5840	58.40%
PPAR gamma	+	0.7996	79.96%
Honey bee toxicity	-	0.7161	71.61%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8753	87.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.78%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.06%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.59%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	96.57%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.46%	95.56%
CHEMBL333	P08253	Matrix metalloproteinase-2	95.38%	96.31%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	93.61%	93.00%
CHEMBL226	P30542	Adenosine A1 receptor	93.10%	95.93%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	92.59%	97.64%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.08%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.69%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.26%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.79%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.28%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.96%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.91%	96.47%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.08%	90.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.84%	86.33%
CHEMBL4072	P07858	Cathepsin B	85.68%	93.67%
CHEMBL4588	P22894	Matrix metalloproteinase 8	85.58%	94.66%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.47%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.03%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.41%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.62%	93.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.43%	97.14%
CHEMBL236	P41143	Delta opioid receptor	82.22%	99.35%
CHEMBL1949	P62937	Cyclophilin A	81.90%	98.57%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.79%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.19%	96.38%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 44448131
• LOTUS: LTS0196459
• wikiData: Q104203255