Unk-Abu(2,3-dehydro)-Thr(1)-D-aThr-D-Tyr-Abu(2,3-dehydro)-D-Gln-Gly-N(Me)aThr-His-(1)

Details

• Internal ID: 9d78c022-905a-4174-b51b-bd0c4317b0cc
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3R)-N-[(E)-1-[[(3S,6S,12R,15E,18R,21R,24S,25R)-12-(3-amino-3-oxopropyl)-15-ethylidene-21-[(1R)-1-hydroxyethyl]-6-[(1S)-1-hydroxyethyl]-18-[(4-hydroxyphenyl)methyl]-3-(1H-imidazol-5-ylmethyl)-7,25-dimethyl-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-24-yl]amino]-1-oxobut-2-en-2-yl]-3-hydroxytetradecanamide
• SMILES (Canonical): CCCCCCCCCCCC(CC(=O)NC(=CC)C(=O)NC1C(OC(=O)C(NC(=O)C(N(C(=O)CNC(=O)C(NC(=O)C(=CC)NC(=O)C(NC(=O)C(NC1=O)C(C)O)CC2=CC=C(C=C2)O)CCC(=O)N)C)C(C)O)CC3=CN=CN3)C)O
• SMILES (Isomeric): CCCCCCCCCCC[C@H](CC(=O)N/C(=C/C)/C(=O)N[C@H]1[C@H](OC(=O)[C@@H](NC(=O)[C@@H](N(C(=O)CNC(=O)[C@H](NC(=O)/C(=C\C)/NC(=O)[C@H](NC(=O)[C@H](NC1=O)[C@@H](C)O)CC2=CC=C(C=C2)O)CCC(=O)N)C)[C@H](C)O)CC3=CN=CN3)C)O
• InChI: InChI=1S/C57H86N12O16/c1-8-11-12-13-14-15-16-17-18-19-38(73)28-45(75)62-39(9-2)52(79)68-48-34(6)85-57(84)43(27-36-29-59-31-61-36)66-56(83)49(33(5)71)69(7)46(76)30-60-50(77)41(24-25-44(58)74)64-51(78)40(10-3)63-53(80)42(26-35-20-22-37(72)23-21-35)65-54(81)47(32(4)70)67-55(48)82/h9-10,20-23,29,31-34,38,41-43,47-49,70-73H,8,11-19,24-28,30H2,1-7H3,(H2,58,74)(H,59,61)(H,60,77)(H,62,75)(H,63,80)(H,64,78)(H,65,81)(H,66,83)(H,67,82)(H,68,79)/b39-9+,40-10+/t32-,33+,34-,38-,41-,42-,43+,47-,48+,49+/m1/s1
• InChI Key: WRRXLNFHXIMOFU-QXTPRVETSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₈₆N₁₂O₁₆
• Molecular Weight: 1195.40 g/mol
• Exact Mass: 1194.62847470 g/mol
• Topological Polar Surface Area (TPSA): 432.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): -1.05
• H-Bond Acceptor: 17
• H-Bond Donor: 14
• Rotatable Bonds: 24

Synonyms

• Unk-Abu(2,3-dehydro)-Thr(1)-D-aThr-D-Tyr-Abu(2,3-dehydro)-D-Gln-Gly-N(Me)aThr-His-(1)
• (3R)-N-[(E)-1-[[(3S,6S,12R,15E,18R,21R,24S,25R)-12-(3-Amino-3-oxopropyl)-15-ethylidene-21-[(1R)-1-hydroxyethyl]-6-[(1S)-1-hydroxyethyl]-18-[(4-hydroxyphenyl)methyl]-3-(1H-imidazol-5-ylmethyl)-7,25-dimethyl-2,5,8,11,14,17,20,23-octaoxo-1-oxa-4,7,10,13,16,19,22-heptazacyclopentacos-24-yl]amino]-1-oxobut-2-en-2-yl]-3-hydroxytetradecanamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6804	68.04%
Caco-2	-	0.8666	86.66%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.3535	35.35%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8007	80.07%
OATP1B3 inhibitior	+	0.9162	91.62%
MATE1 inhibitior	-	0.8809	88.09%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9717	97.17%
P-glycoprotein inhibitior	+	0.7423	74.23%
P-glycoprotein substrate	+	0.8848	88.48%
CYP3A4 substrate	+	0.7471	74.71%
CYP2C9 substrate	-	0.8056	80.56%
CYP2D6 substrate	-	0.8631	86.31%
CYP3A4 inhibition	-	0.5728	57.28%
CYP2C9 inhibition	-	0.8482	84.82%
CYP2C19 inhibition	-	0.8539	85.39%
CYP2D6 inhibition	-	0.8889	88.89%
CYP1A2 inhibition	-	0.8454	84.54%
CYP2C8 inhibition	+	0.8462	84.62%
CYP inhibitory promiscuity	-	0.9109	91.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5697	56.97%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.8969	89.69%
Skin irritation	-	0.7730	77.30%
Skin corrosion	-	0.9232	92.32%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7072	70.72%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8625	86.25%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9889	98.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6999	69.99%
Acute Oral Toxicity (c)	III	0.5944	59.44%
Estrogen receptor binding	+	0.6609	66.09%
Androgen receptor binding	+	0.7289	72.89%
Thyroid receptor binding	+	0.6617	66.17%
Glucocorticoid receptor binding	+	0.7518	75.18%
Aromatase binding	+	0.6970	69.70%
PPAR gamma	+	0.7470	74.70%
Honey bee toxicity	-	0.6526	65.26%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5878	58.78%
Fish aquatic toxicity	+	0.9235	92.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3038469	P24941	CDK2/Cyclin A	99.38%	91.38%
CHEMBL2581	P07339	Cathepsin D	99.26%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.23%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.23%	94.45%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	97.45%	93.10%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.27%	91.11%
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	96.47%	95.20%
CHEMBL5103	Q969S8	Histone deacetylase 10	96.35%	90.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.83%	99.17%
CHEMBL255	P29275	Adenosine A2b receptor	95.35%	98.59%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	94.90%	97.64%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	94.48%	96.90%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	93.46%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	93.19%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.88%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.85%	85.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	92.60%	97.33%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	91.70%	92.88%
CHEMBL301	P24941	Cyclin-dependent kinase 2	89.69%	91.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.49%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.65%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.09%	99.23%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	87.90%	85.00%
CHEMBL2514	O95665	Neurotensin receptor 2	87.82%	100.00%
CHEMBL4588	P22894	Matrix metalloproteinase 8	87.36%	94.66%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.27%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.46%	95.56%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.01%	88.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.98%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.94%	93.56%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	85.89%	85.83%
CHEMBL2535	P11166	Glucose transporter	85.41%	98.75%
CHEMBL236	P41143	Delta opioid receptor	85.00%	99.35%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.94%	82.38%
CHEMBL3837	P07711	Cathepsin L	84.86%	96.61%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.57%	89.67%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.40%	93.03%
CHEMBL4040	P28482	MAP kinase ERK2	83.50%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	82.42%	90.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.16%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.70%	93.00%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	81.48%	91.81%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.38%	97.25%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	81.38%	88.42%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.87%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.45%	91.24%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.10%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9876915
• LOTUS: LTS0269073
• wikiData: Q77497357