Cyclolinopeptide B

Details

• Internal ID: d0f09d76-038b-46a9-bed3-6e13e22bd1e2
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: (3S,9S,12S,15S,18S,21S,24S,27S,30S)-24,27-dibenzyl-9,18-bis[(2S)-butan-2-yl]-12-(2-methylpropyl)-15-(2-methylsulfanylethyl)-21-propan-2-yl-1,7,10,13,16,19,22,25,28-nonazatricyclo[28.3.0.03,7]tritriacontane-2,8,11,14,17,20,23,26,29-nonone
• SMILES (Canonical): CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)N3CCCC3C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C(C)C)CC4=CC=CC=C4)CC5=CC=CC=C5)C(C)CC)CC(C)C)CCSC
• SMILES (Isomeric): CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N3CCC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(C)C)CC4=CC=CC=C4)CC5=CC=CC=C5)[C@@H](C)CC)CC(C)C)CCSC
• InChI: InChI=1S/C56H83N9O9S/c1-10-35(7)46-54(72)57-39(26-29-75-9)48(66)58-40(30-33(3)4)50(68)63-47(36(8)11-2)56(74)65-28-19-25-44(65)55(73)64-27-18-24-43(64)52(70)60-41(31-37-20-14-12-15-21-37)49(67)59-42(32-38-22-16-13-17-23-38)51(69)61-45(34(5)6)53(71)62-46/h12-17,20-23,33-36,39-47H,10-11,18-19,24-32H2,1-9H3,(H,57,72)(H,58,66)(H,59,67)(H,60,70)(H,61,69)(H,62,71)(H,63,68)/t35-,36-,39-,40-,41-,42-,43-,44-,45-,46-,47-/m0/s1
• InChI Key: BRDMGDLQYNAXNM-NGFONASMSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₈₃N₉O₉S
• Molecular Weight: 1058.40 g/mol
• Exact Mass: 1057.60344643 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: 7.10
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 14

Synonyms

• cyclo(Met(1)-Leu(2)-Ile(3)-Pro(4)-Pro(5)-Phe(6)-Phe(7)-Val(8)-Ile(9))

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9070	90.70%
Caco-2	-	0.8657	86.57%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Lysosomes	0.4669	46.69%
OATP2B1 inhibitior	-	0.7081	70.81%
OATP1B1 inhibitior	+	0.8624	86.24%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9506	95.06%
P-glycoprotein inhibitior	+	0.7569	75.69%
P-glycoprotein substrate	+	0.8191	81.91%
CYP3A4 substrate	+	0.6521	65.21%
CYP2C9 substrate	-	0.6124	61.24%
CYP2D6 substrate	-	0.8167	81.67%
CYP3A4 inhibition	-	0.8182	81.82%
CYP2C9 inhibition	-	0.7962	79.62%
CYP2C19 inhibition	-	0.8138	81.38%
CYP2D6 inhibition	-	0.8777	87.77%
CYP1A2 inhibition	-	0.9468	94.68%
CYP2C8 inhibition	+	0.5647	56.47%
CYP inhibitory promiscuity	-	0.9771	97.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6845	68.45%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9034	90.34%
Skin irritation	-	0.7762	77.62%
Skin corrosion	-	0.9226	92.26%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6824	68.24%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.6479	64.79%
skin sensitisation	-	0.8986	89.86%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5102	51.02%
Acute Oral Toxicity (c)	III	0.7155	71.55%
Estrogen receptor binding	+	0.8093	80.93%
Androgen receptor binding	+	0.6997	69.97%
Thyroid receptor binding	+	0.5733	57.33%
Glucocorticoid receptor binding	+	0.6795	67.95%
Aromatase binding	+	0.6106	61.06%
PPAR gamma	+	0.8033	80.33%
Honey bee toxicity	-	0.7745	77.45%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9751	97.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.89%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.83%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.51%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	96.03%	90.17%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	95.92%	97.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.69%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	94.55%	90.08%
CHEMBL333	P08253	Matrix metalloproteinase-2	94.34%	96.31%
CHEMBL1978	P11511	Cytochrome P450 19A1	92.89%	91.76%
CHEMBL220	P22303	Acetylcholinesterase	92.86%	94.45%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	92.33%	82.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.31%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.13%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	91.03%	95.93%
CHEMBL1902	P62942	FK506-binding protein 1A	89.39%	97.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.17%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.55%	94.45%
CHEMBL3202	P48147	Prolyl endopeptidase	87.25%	90.65%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.12%	93.03%
CHEMBL228	P31645	Serotonin transporter	85.81%	95.51%
CHEMBL3524	P56524	Histone deacetylase 4	85.56%	92.97%
CHEMBL1937	Q92769	Histone deacetylase 2	85.55%	94.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.98%	90.71%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	84.87%	98.33%
CHEMBL4071	P08311	Cathepsin G	84.57%	94.64%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.35%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.20%	86.33%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	82.78%	92.67%
CHEMBL5203	P33316	dUTP pyrophosphatase	82.66%	99.18%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.00%	93.56%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	81.09%	95.48%
CHEMBL4616	Q92847	Ghrelin receptor	80.30%	92.00%
CHEMBL2443	P49862	Kallikrein 7	80.30%	94.00%

Plants that contains it

• Linum usitatissimum

Cross-Links

• PubChem: 10581956
• LOTUS: LTS0038280
• wikiData: Q104944734