Jessenipeptin

Details

• Internal ID: ae7855b3-5111-447d-96b6-919484ba2f73
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2R)-N-[(2R,3R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-1-[[(2R)-1-[[(Z)-1-[[(3S,6R,9S,12S,15R,16R)-9-(2-aminoethyl)-3-benzyl-6-(hydroxymethyl)-12,16-dimethyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetrazacyclohexadec-15-yl]amino]-1-oxobut-2-en-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-1-[(Z)-2-[[(3R)-3-hydroxydecanoyl]amino]but-2-enoyl]pyrrolidine-2-carboxamide
• InChI: InChI=1S/C91H148N20O24/c1-21-25-26-27-31-35-58(114)42-67(115)99-60(24-4)90(133)111-39-32-36-66(111)84(127)109-71(49(13)22-2)88(131)108-69(47(9)10)86(129)96-51(15)74(117)93-50(14)73(116)94-54(18)77(120)107-70(48(11)12)87(130)105-64(43-112)82(125)95-55(19)78(121)106-68(46(7)8)85(128)97-53(17)76(119)102-62(40-45(5)6)81(124)100-59(23-3)79(122)110-72-56(20)135-91(134)63(41-57-33-29-28-30-34-57)103-83(126)65(44-113)104-80(123)61(37-38-92)101-75(118)52(16)98-89(72)132/h23-24,28-30,33-34,45-56,58,61-66,68-72,112-114H,21-22,25-27,31-32,35-44,92H2,1-20H3,(H,93,117)(H,94,116)(H,95,125)(H,96,129)(H,97,128)(H,98,132)(H,99,115)(H,100,124)(H,101,118)(H,102,119)(H,103,126)(H,104,123)(H,105,130)(H,106,121)(H,107,120)(H,108,131)(H,109,127)(H,110,122)/b59-23-,60-24-/t49-,50-,51-,52+,53-,54+,55-,56-,58-,61+,62-,63+,64-,65-,66-,68-,69-,70-,71-,72-/m1/s1
• InChI Key: RCRYELMDBHQIMX-JRGFPVMHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉₁H₁₄₈N₂₀O₂₄
• Molecular Weight: 1906.30 g/mol
• Exact Mass: 1905.09753567 g/mol
• Topological Polar Surface Area (TPSA): 657.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): -3.41
• H-Bond Acceptor: 25
• H-Bond Donor: 22
• Rotatable Bonds: 49

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7451	74.51%
Caco-2	-	0.8606	86.06%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Lysosomes	0.4662	46.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8167	81.67%
OATP1B3 inhibitior	+	0.9156	91.56%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9801	98.01%
P-glycoprotein inhibitior	+	0.7420	74.20%
P-glycoprotein substrate	+	0.8842	88.42%
CYP3A4 substrate	+	0.7539	75.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8356	83.56%
CYP3A4 inhibition	-	0.5747	57.47%
CYP2C9 inhibition	-	0.8722	87.22%
CYP2C19 inhibition	-	0.8678	86.78%
CYP2D6 inhibition	-	0.9127	91.27%
CYP1A2 inhibition	-	0.8963	89.63%
CYP2C8 inhibition	+	0.8107	81.07%
CYP inhibitory promiscuity	-	0.9452	94.52%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.5667	56.67%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.8956	89.56%
Skin irritation	-	0.7649	76.49%
Skin corrosion	-	0.9126	91.26%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7388	73.88%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5209	52.09%
skin sensitisation	-	0.8561	85.61%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.8093	80.93%
Acute Oral Toxicity (c)	III	0.5719	57.19%
Estrogen receptor binding	+	0.6021	60.21%
Androgen receptor binding	+	0.7610	76.10%
Thyroid receptor binding	+	0.7320	73.20%
Glucocorticoid receptor binding	+	0.7963	79.63%
Aromatase binding	+	0.7579	75.79%
PPAR gamma	+	0.7815	78.15%
Honey bee toxicity	-	0.6827	68.27%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6080	60.80%
Fish aquatic toxicity	+	0.9435	94.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.97%	98.95%
CHEMBL3837	P07711	Cathepsin L	99.95%	96.61%
CHEMBL230	P35354	Cyclooxygenase-2	99.80%	89.63%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	99.12%	97.64%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	98.86%	98.33%
CHEMBL4801	P29466	Caspase-1	98.10%	96.85%
CHEMBL4072	P07858	Cathepsin B	97.77%	93.67%
CHEMBL3359	P21462	Formyl peptide receptor 1	97.77%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.76%	96.09%
CHEMBL2514	O95665	Neurotensin receptor 2	97.35%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.23%	97.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	96.96%	96.47%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.76%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.71%	95.56%
CHEMBL4588	P22894	Matrix metalloproteinase 8	96.48%	94.66%
CHEMBL221	P23219	Cyclooxygenase-1	96.30%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	96.09%	97.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.30%	91.11%
CHEMBL321	P14780	Matrix metalloproteinase 9	94.39%	92.12%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	94.24%	88.42%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	92.73%	100.00%
CHEMBL3468	P55210	Caspase-7	91.51%	95.68%
CHEMBL340	P08684	Cytochrome P450 3A4	91.38%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	91.35%	100.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	91.23%	82.38%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.17%	90.71%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	89.63%	91.81%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.58%	93.03%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.44%	97.29%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.24%	97.25%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	88.70%	90.24%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	88.52%	95.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.44%	100.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.25%	93.10%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.02%	93.00%
CHEMBL237	P41145	Kappa opioid receptor	86.87%	98.10%
CHEMBL1293287	P14735	Insulin-degrading enzyme	86.79%	88.10%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.66%	90.08%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	86.66%	97.23%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	86.60%	97.50%
CHEMBL333	P08253	Matrix metalloproteinase-2	86.29%	96.31%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.18%	92.08%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.79%	92.88%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	85.44%	98.24%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.36%	94.80%
CHEMBL2327	P21452	Neurokinin 2 receptor	85.07%	98.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.75%	90.93%
CHEMBL4581	P52732	Kinesin-like protein 1	84.67%	93.18%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.07%	96.90%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.10%	96.00%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	83.01%	96.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.41%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.22%	95.89%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.93%	92.86%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.00%	92.32%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 145720625
• LOTUS: LTS0198067
• wikiData: Q105233930