cyclo[Ala-Val-ObAla(3-hexyl)-Gly-Val-Leu]

Details

• Internal ID: 14cf932e-0251-4a4a-8705-478fa7736e1d
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3S,6S,9S,12S)-19-hexyl-6-methyl-9-(2-methylpropyl)-3,12-di(propan-2-yl)-1-oxa-4,7,10,13,16-pentazacyclononadecane-2,5,8,11,14,17-hexone
• SMILES (Canonical): CCCCCCC1CC(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O1)C(C)C)C)CC(C)C)C(C)C
• SMILES (Isomeric): CCCCCCC1CC(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O1)C(C)C)C)CC(C)C)C(C)C
• InChI: InChI=1S/C30H53N5O7/c1-9-10-11-12-13-21-15-23(36)31-16-24(37)34-25(18(4)5)29(40)33-22(14-17(2)3)28(39)32-20(8)27(38)35-26(19(6)7)30(41)42-21/h17-22,25-26H,9-16H2,1-8H3,(H,31,36)(H,32,39)(H,33,40)(H,34,37)(H,35,38)/t20-,21?,22-,25-,26-/m0/s1
• InChI Key: QWBKHPNGPXORRV-SKZWQOKYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₃N₅O₇
• Molecular Weight: 595.80 g/mol
• Exact Mass: 595.39449905 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8079	80.79%
Caco-2	-	0.8139	81.39%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6359	63.59%
OATP2B1 inhibitior	-	0.5784	57.84%
OATP1B1 inhibitior	+	0.8627	86.27%
OATP1B3 inhibitior	+	0.8906	89.06%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6597	65.97%
P-glycoprotein inhibitior	+	0.7463	74.63%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6168	61.68%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.8701	87.01%
CYP3A4 inhibition	-	0.8201	82.01%
CYP2C9 inhibition	-	0.9375	93.75%
CYP2C19 inhibition	-	0.9210	92.10%
CYP2D6 inhibition	-	0.9225	92.25%
CYP1A2 inhibition	-	0.9315	93.15%
CYP2C8 inhibition	-	0.5773	57.73%
CYP inhibitory promiscuity	-	0.9865	98.65%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6348	63.48%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9177	91.77%
Skin irritation	-	0.8040	80.40%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4765	47.65%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8812	88.12%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6455	64.55%
Acute Oral Toxicity (c)	III	0.6818	68.18%
Estrogen receptor binding	+	0.7552	75.52%
Androgen receptor binding	+	0.6246	62.46%
Thyroid receptor binding	+	0.5724	57.24%
Glucocorticoid receptor binding	+	0.7304	73.04%
Aromatase binding	+	0.6683	66.83%
PPAR gamma	+	0.6317	63.17%
Honey bee toxicity	-	0.8590	85.90%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6734	67.34%
Fish aquatic toxicity	+	0.6762	67.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.10%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.74%	97.25%
CHEMBL5103	Q969S8	Histone deacetylase 10	97.36%	90.08%
CHEMBL2996	Q05655	Protein kinase C delta	95.94%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	95.77%	98.03%
CHEMBL230	P35354	Cyclooxygenase-2	94.92%	89.63%
CHEMBL1949	P62937	Cyclophilin A	94.74%	98.57%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	94.73%	90.24%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.25%	91.11%
CHEMBL3524	P56524	Histone deacetylase 4	93.18%	92.97%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.83%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	92.54%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.49%	97.09%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	90.66%	97.29%
CHEMBL3310	Q96DB2	Histone deacetylase 11	90.17%	88.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.54%	93.56%
CHEMBL1937	Q92769	Histone deacetylase 2	89.51%	94.75%
CHEMBL255	P29275	Adenosine A2b receptor	87.04%	98.59%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	86.56%	91.71%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.15%	95.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.23%	96.47%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	85.18%	96.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.09%	99.17%
CHEMBL4588	P22894	Matrix metalloproteinase 8	84.97%	94.66%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	84.19%	97.64%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.42%	100.00%
CHEMBL325	Q13547	Histone deacetylase 1	82.96%	95.92%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.85%	92.88%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.85%	90.71%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	82.73%	91.81%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.70%	96.90%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.47%	97.14%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	81.71%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.59%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.24%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	81.21%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.88%	99.23%
CHEMBL321	P14780	Matrix metalloproteinase 9	80.82%	92.12%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.69%	83.10%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.42%	82.38%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.14%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.12%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.06%	89.34%

Plants that contains it

• Gymnosporia acuminata

Cross-Links

• PubChem: 102145514
• NPASS: NPC72778