(2R)-2-[[[(1S,4S,10S,13S,19S,22S,25S,29R,30S,33S,44S)-33-benzyl-2,11,21,24,31,34,41,46,48-nonahydroxy-30-[[1-hydroxy-2-[[1-hydroxy-2-[[(2S)-1-hydroxy-2-(1-hydroxyethylideneamino)-3-(4-hydroxyphenyl)propylidene]amino]ethylidene]amino]ethylidene]amino]-4-[(4-hydroxyphenyl)methyl]-22-(1H-indol-3-ylmethyl)-29-methyl-5,16,27-trioxo-15,28-dioxa-3,6,12,20,23,32,35,40,45,47-decazatetracyclo[17.16.11.213,25.06,10]octatetraconta-2,11,20,23,31,34,40,45,47-nonaen-44-yl]-hydroxymethylidene]amino]-3-(4-hydroxyphenyl)propanoic acid

Details

• Internal ID: 15eecba1-cb00-4b21-ba13-fd436aced54f
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2R)-2-[[[(1S,4S,10S,13S,19S,22S,25S,29R,30S,33S,44S)-33-benzyl-2,11,21,24,31,34,41,46,48-nonahydroxy-30-[[1-hydroxy-2-[[1-hydroxy-2-[[(2S)-1-hydroxy-2-(1-hydroxyethylideneamino)-3-(4-hydroxyphenyl)propylidene]amino]ethylidene]amino]ethylidene]amino]-4-[(4-hydroxyphenyl)methyl]-22-(1H-indol-3-ylmethyl)-29-methyl-5,16,27-trioxo-15,28-dioxa-3,6,12,20,23,32,35,40,45,47-decazatetracyclo[17.16.11.213,25.06,10]octatetraconta-2,11,20,23,31,34,40,45,47-nonaen-44-yl]-hydroxymethylidene]amino]-3-(4-hydroxyphenyl)propanoic acid
• SMILES (Canonical): CC1C(C(=NC(C(=NC2CCCCN=C(CCC(N=C(C3CCC(=O)OCC(C(=NC(CC(=O)O1)C(=NC(C(=N3)O)CC4=CNC5=CC=CC=C54)O)O)N=C(C6CCCN6C(=O)C(N=C2O)CC7=CC=C(C=C7)O)O)O)C(=NC(CC8=CC=C(C=C8)O)C(=O)O)O)O)O)CC9=CC=CC=C9)O)N=C(CN=C(CN=C(C(CC1=CC=C(C=C1)O)N=C(C)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H](C(=N[C@H](C(=N[C@H]2CCCCN=C(CC[C@H](N=C([C@@H]3CCC(=O)OC[C@@H](C(=N[C@@H](CC(=O)O1)C(=N[C@H](C(=N3)O)CC4=CNC5=CC=CC=C54)O)O)N=C([C@@H]6CCCN6C(=O)[C@@H](N=C2O)CC7=CC=C(C=C7)O)O)O)C(=N[C@H](CC8=CC=C(C=C8)O)C(=O)O)O)O)O)CC9=CC=CC=C9)O)N=C(CN=C(CN=C([C@H](CC1=CC=C(C=C1)O)N=C(C)O)O)O)O
• InChI: InChI=1S/C85H100N16O24/c1-45-73(100-70(108)43-88-69(107)42-89-74(111)60(90-46(2)102)36-48-17-23-52(103)24-18-48)83(120)96-61(35-47-11-4-3-5-12-47)78(115)91-57-15-8-9-33-86-68(106)31-29-58(77(114)98-65(85(122)123)38-50-21-27-54(105)28-22-50)92-76(113)59-30-32-71(109)124-44-66(99-82(119)67-16-10-34-101(67)84(121)64(97-75(57)112)37-49-19-25-53(104)26-20-49)81(118)95-63(40-72(110)125-45)80(117)94-62(79(116)93-59)39-51-41-87-56-14-7-6-13-55(51)56/h3-7,11-14,17-28,41,45,57-67,73,87,103-105H,8-10,15-16,29-40,42-44H2,1-2H3,(H,86,106)(H,88,107)(H,89,111)(H,90,102)(H,91,115)(H,92,113)(H,93,116)(H,94,117)(H,95,118)(H,96,120)(H,97,112)(H,98,114)(H,99,119)(H,100,108)(H,122,123)/t45-,57+,58+,59+,60+,61+,62+,63+,64+,65-,66+,67+,73+/m1/s1
• InChI Key: GZWAMQUNOCFCLH-DZWASQLJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₈₅H₁₀₀N₁₆O₂₄
• Molecular Weight: 1729.80 g/mol
• Exact Mass: 1728.70963812 g/mol
• Topological Polar Surface Area (TPSA): 643.00 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 8.98
• H-Bond Acceptor: 23
• H-Bond Donor: 19
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7660	76.60%
Caco-2	-	0.8564	85.64%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5469	54.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8068	80.68%
OATP1B3 inhibitior	+	0.9197	91.97%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7609	76.09%
BSEP inhibitior	+	0.9790	97.90%
P-glycoprotein inhibitior	+	0.7422	74.22%
P-glycoprotein substrate	+	0.8487	84.87%
CYP3A4 substrate	+	0.7573	75.73%
CYP2C9 substrate	-	0.8060	80.60%
CYP2D6 substrate	-	0.8377	83.77%
CYP3A4 inhibition	+	0.5969	59.69%
CYP2C9 inhibition	-	0.8752	87.52%
CYP2C19 inhibition	-	0.7723	77.23%
CYP2D6 inhibition	-	0.8487	84.87%
CYP1A2 inhibition	-	0.9403	94.03%
CYP2C8 inhibition	+	0.8434	84.34%
CYP inhibitory promiscuity	-	0.5723	57.23%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5863	58.63%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.8956	89.56%
Skin irritation	-	0.8045	80.45%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.5028	50.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7285	72.85%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.5198	51.98%
skin sensitisation	-	0.8909	89.09%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7594	75.94%
Acute Oral Toxicity (c)	III	0.6280	62.80%
Estrogen receptor binding	-	0.5451	54.51%
Androgen receptor binding	+	0.7720	77.20%
Thyroid receptor binding	+	0.8109	81.09%
Glucocorticoid receptor binding	+	0.8325	83.25%
Aromatase binding	+	0.7709	77.09%
PPAR gamma	+	0.7860	78.60%
Honey bee toxicity	-	0.6400	64.00%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8747	87.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.94%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	99.81%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.98%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.76%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	96.69%	91.71%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	96.51%	97.64%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.87%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.57%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.35%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.34%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.93%	99.23%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.23%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.18%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.81%	95.89%
CHEMBL2535	P11166	Glucose transporter	91.59%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.26%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	88.19%	83.82%
CHEMBL5805	Q9NR97	Toll-like receptor 8	87.85%	96.25%
CHEMBL1902	P62942	FK506-binding protein 1A	86.78%	97.05%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.98%	88.56%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	83.86%	91.81%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.37%	95.71%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.01%	95.48%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.40%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163192154
• LOTUS: LTS0017696
• wikiData: Q104203122