Cyclolinopeptide F

Details

• Internal ID: dcf47ee7-2db7-40fa-baf0-3404eb8140a6
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (3S,6S,9S,12S,15S,18S,21S,24S)-18,21-dibenzyl-15-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-3,9-bis(2-methylsulfinylethyl)-12-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): CC(C)CC1C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCS(=O)C)C(C)C)CC3=CNC4=CC=CC=C43)CC5=CC=CC=C5)CC6=CC=CC=C6)CCS(=O)C
• SMILES (Isomeric): CC(C)C[C@H]1C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCS(=O)C)C(C)C)CC3=CNC4=CC=CC=C43)CC5=CC=CC=C5)CC6=CC=CC=C6)CCS(=O)C
• InChI: InChI=1S/C55H73N9O10S2/c1-33(2)28-42-49(66)58-41(24-27-76(6)74)55(72)64-25-15-22-46(64)53(70)62-44(30-36-18-11-8-12-19-36)51(68)60-43(29-35-16-9-7-10-17-35)50(67)61-45(31-37-32-56-39-21-14-13-20-38(37)39)52(69)63-47(34(3)4)54(71)57-40(48(65)59-42)23-26-75(5)73/h7-14,16-21,32-34,40-47,56H,15,22-31H2,1-6H3,(H,57,71)(H,58,66)(H,59,65)(H,60,68)(H,61,67)(H,62,70)(H,63,69)/t40-,41-,42-,43-,44-,45-,46-,47-,75?,76?/m0/s1
• InChI Key: OPPHXUQOVAMNAS-AEEQZTKLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₇₃N₉O₁₀S₂
• Molecular Weight: 1084.40 g/mol
• Exact Mass: 1083.49218191 g/mol
• Topological Polar Surface Area (TPSA): 312.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 15

Synonyms

• CHEMBL3787695
• CHEBI:157786
• (3S,6S,9S,12S,15S,18S,21S,24S)-18,21-dibenzyl-15-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-3,9-bis(2-methylsulinylethyl)-12-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
• (3S,6S,9S,12S,15S,18S,21S,26aS)-3,6-dibenzyl-9-(1H-indol-3-ylmethyl)-15,21-bis(2-methanesulfinylethyl)-18-(2-methylpropyl)-12-(propan-2-yl)-hexacosahydropyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-1,4,7,10,13,16,19,22-octone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9413	94.13%
Caco-2	-	0.8670	86.70%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4063	40.63%
OATP2B1 inhibitior	-	0.5708	57.08%
OATP1B1 inhibitior	+	0.8782	87.82%
OATP1B3 inhibitior	+	0.9303	93.03%
MATE1 inhibitior	-	0.8035	80.35%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9853	98.53%
P-glycoprotein inhibitior	+	0.7577	75.77%
P-glycoprotein substrate	+	0.8413	84.13%
CYP3A4 substrate	+	0.7039	70.39%
CYP2C9 substrate	-	0.8092	80.92%
CYP2D6 substrate	-	0.8140	81.40%
CYP3A4 inhibition	-	0.6738	67.38%
CYP2C9 inhibition	-	0.7238	72.38%
CYP2C19 inhibition	-	0.7949	79.49%
CYP2D6 inhibition	-	0.8757	87.57%
CYP1A2 inhibition	-	0.8524	85.24%
CYP2C8 inhibition	+	0.5080	50.80%
CYP inhibitory promiscuity	-	0.9067	90.67%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6800	68.00%
Carcinogenicity (trinary)	Non-required	0.6356	63.56%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9038	90.38%
Skin irritation	-	0.7707	77.07%
Skin corrosion	-	0.9216	92.16%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7147	71.47%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.6341	63.41%
skin sensitisation	-	0.8594	85.94%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7095	70.95%
Acute Oral Toxicity (c)	III	0.6441	64.41%
Estrogen receptor binding	+	0.7979	79.79%
Androgen receptor binding	+	0.5622	56.22%
Thyroid receptor binding	+	0.6127	61.27%
Glucocorticoid receptor binding	+	0.6058	60.58%
Aromatase binding	+	0.5990	59.90%
PPAR gamma	+	0.7749	77.49%
Honey bee toxicity	-	0.7697	76.97%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9444	94.44%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.80%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.40%	91.11%
CHEMBL333	P08253	Matrix metalloproteinase-2	98.06%	96.31%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	97.88%	97.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.69%	96.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	97.59%	90.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.26%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.86%	95.56%
CHEMBL1978	P11511	Cytochrome P450 19A1	95.83%	91.76%
CHEMBL3524	P56524	Histone deacetylase 4	95.10%	92.97%
CHEMBL3310	Q96DB2	Histone deacetylase 11	95.05%	88.56%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	94.68%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.23%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	91.58%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.47%	97.09%
CHEMBL5203	P33316	dUTP pyrophosphatase	91.26%	99.18%
CHEMBL1937	Q92769	Histone deacetylase 2	90.72%	94.75%
CHEMBL1902	P62942	FK506-binding protein 1A	90.40%	97.05%
CHEMBL321	P14780	Matrix metalloproteinase 9	89.62%	92.12%
CHEMBL228	P31645	Serotonin transporter	89.38%	95.51%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.09%	94.45%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.91%	82.38%
CHEMBL5805	Q9NR97	Toll-like receptor 8	87.06%	96.25%
CHEMBL213	P08588	Beta-1 adrenergic receptor	85.78%	95.56%
CHEMBL3202	P48147	Prolyl endopeptidase	85.23%	90.65%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.24%	92.67%
CHEMBL1949	P62937	Cyclophilin A	84.21%	98.57%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	84.15%	91.43%
CHEMBL1914	P06276	Butyrylcholinesterase	83.23%	95.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.71%	93.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.96%	92.62%
CHEMBL4644	P41968	Melanocortin receptor 3	81.25%	99.52%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	81.09%	83.10%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.97%	96.47%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	80.67%	99.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.29%	95.71%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.02%	98.33%

Plants that contains it

• Linum usitatissimum
• Papaver somniferum

Cross-Links

• PubChem: 6398538
• NPASS: NPC31385
• ChEMBL: CHEMBL3787695
• LOTUS: LTS0245408
• wikiData: Q105196491