cyclo[Ile-DL-Met(O)-Leu-Val-Phe-Pro-Leu-Phe]

Details

• Internal ID: cba14d59-5e12-44a1-94c3-8d53612fc852
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Cyclic peptides
• IUPAC Name: (3S,6S,9S,15S,18S,21S,24S)-3,18-dibenzyl-15-[(2S)-butan-2-yl]-9,21-bis(2-methylpropyl)-12-(2-methylsulfinylethyl)-6-propan-2-yl-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
• SMILES (Canonical): CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)N1)CC3=CC=CC=C3)CC(C)C)CC4=CC=CC=C4)C(C)C)CC(C)C)CCS(=O)C
• SMILES (Isomeric): CC[C@H](C)[C@H]1C(=O)NC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC3=CC=CC=C3)CC(C)C)CC4=CC=CC=C4)C(C)C)CC(C)C)CCS(=O)C
• InChI: InChI=1S/C51H76N8O9S/c1-10-33(8)43-50(66)52-36(23-25-69(9)68)44(60)53-38(27-31(4)5)46(62)57-42(32(6)7)49(65)56-40(29-35-20-15-12-16-21-35)51(67)59-24-17-22-41(59)48(64)55-37(26-30(2)3)45(61)54-39(47(63)58-43)28-34-18-13-11-14-19-34/h11-16,18-21,30-33,36-43H,10,17,22-29H2,1-9H3,(H,52,66)(H,53,60)(H,54,61)(H,55,64)(H,56,65)(H,57,62)(H,58,63)/t33-,36?,37-,38-,39-,40-,41-,42-,43-,69?/m0/s1
• InChI Key: IWEUOAFIXUXUNB-IJFYDUSLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₁H₇₆N₈O₉S
• Molecular Weight: 977.30 g/mol
• Exact Mass: 976.54559721 g/mol
• Topological Polar Surface Area (TPSA): 260.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 2.43
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9322	93.22%
Caco-2	-	0.8660	86.60%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.5049	50.49%
OATP2B1 inhibitior	-	0.5700	57.00%
OATP1B1 inhibitior	+	0.8738	87.38%
OATP1B3 inhibitior	+	0.9312	93.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9598	95.98%
P-glycoprotein inhibitior	+	0.7616	76.16%
P-glycoprotein substrate	+	0.8324	83.24%
CYP3A4 substrate	+	0.6472	64.72%
CYP2C9 substrate	-	0.5779	57.79%
CYP2D6 substrate	-	0.8027	80.27%
CYP3A4 inhibition	-	0.8067	80.67%
CYP2C9 inhibition	-	0.7626	76.26%
CYP2C19 inhibition	-	0.8256	82.56%
CYP2D6 inhibition	-	0.8521	85.21%
CYP1A2 inhibition	-	0.8876	88.76%
CYP2C8 inhibition	+	0.4895	48.95%
CYP inhibitory promiscuity	-	0.9811	98.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6700	67.00%
Carcinogenicity (trinary)	Non-required	0.6486	64.86%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9072	90.72%
Skin irritation	-	0.7687	76.87%
Skin corrosion	-	0.9172	91.72%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7346	73.46%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.5483	54.83%
skin sensitisation	-	0.8612	86.12%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.5941	59.41%
Acute Oral Toxicity (c)	III	0.6447	64.47%
Estrogen receptor binding	+	0.7799	77.99%
Androgen receptor binding	+	0.6348	63.48%
Thyroid receptor binding	+	0.5573	55.73%
Glucocorticoid receptor binding	+	0.6274	62.74%
Aromatase binding	+	0.5898	58.98%
PPAR gamma	+	0.7750	77.50%
Honey bee toxicity	-	0.7873	78.73%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9655	96.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.85%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.90%	96.09%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	95.64%	97.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.42%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	94.31%	82.38%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.94%	90.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.56%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	92.57%	90.17%
CHEMBL3524	P56524	Histone deacetylase 4	92.35%	92.97%
CHEMBL333	P08253	Matrix metalloproteinase-2	91.68%	96.31%
CHEMBL1978	P11511	Cytochrome P450 19A1	91.63%	91.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.66%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.13%	95.89%
CHEMBL5203	P33316	dUTP pyrophosphatase	88.20%	99.18%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.61%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.56%	97.14%
CHEMBL1902	P62942	FK506-binding protein 1A	86.36%	97.05%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.26%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.99%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.17%	91.11%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.71%	96.47%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.42%	97.25%
CHEMBL4616	Q92847	Ghrelin receptor	84.29%	92.00%
CHEMBL3202	P48147	Prolyl endopeptidase	83.63%	90.65%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	83.26%	92.67%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.09%	93.03%
CHEMBL220	P22303	Acetylcholinesterase	82.48%	94.45%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.12%	95.48%
CHEMBL1937	Q92769	Histone deacetylase 2	81.86%	94.75%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.42%	90.93%

Plants that contains it

• Linum usitatissimum

Cross-Links

• PubChem: 100953616
• LOTUS: LTS0112568
• wikiData: Q105121570