3-[(3Z,6S,9R,15S,18R,21S,24S,27R,30S,31R)-15,21,24-tris(carboxymethyl)-30-[[(2S)-1,3-dihydroxy-2-[[hydroxy-(3-propyloxiran-2-yl)methylidene]amino]propylidene]amino]-9-[(1S)-1,2-dihydroxy-2-iminoethyl]-5,8,11,14,17,20,23,26,29-nonahydroxy-18-(4-hydroxyphenyl)-27-(1H-indol-3-ylmethyl)-3-(1H-indol-3-ylmethylidene)-31-methyl-2-oxo-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriaconta-4,7,10,13,16,19,22,25,28-nonaen-6-yl]propanoic acid

Details

• Internal ID: 144309f7-af36-4137-9bc1-0e1d965b75a1
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: 3-[(3Z,6S,9R,15S,18R,21S,24S,27R,30S,31R)-15,21,24-tris(carboxymethyl)-30-[[(2S)-1,3-dihydroxy-2-[[hydroxy-(3-propyloxiran-2-yl)methylidene]amino]propylidene]amino]-9-[(1S)-1,2-dihydroxy-2-iminoethyl]-5,8,11,14,17,20,23,26,29-nonahydroxy-18-(4-hydroxyphenyl)-27-(1H-indol-3-ylmethyl)-3-(1H-indol-3-ylmethylidene)-31-methyl-2-oxo-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriaconta-4,7,10,13,16,19,22,25,28-nonaen-6-yl]propanoic acid
• SMILES (Canonical): CCCC1C(O1)C(=NC(CO)C(=NC2C(OC(=O)C(=CC3=CNC4=CC=CC=C43)N=C(C(N=C(C(N=C(CN=C(C(N=C(C(N=C(C(N=C(C(N=C(C(N=C2O)CC5=CNC6=CC=CC=C65)O)CC(=O)O)O)CC(=O)O)O)C7=CC=C(C=C7)O)O)CC(=O)O)O)O)C(C(=N)O)O)O)CCC(=O)O)O)C)O)O
• SMILES (Isomeric): CCCC1C(O1)C(=N[C@@H](CO)C(=N[C@H]2[C@H](OC(=O)/C(=C/C3=CNC4=CC=CC=C43)/N=C([C@@H](N=C([C@H](N=C(CN=C([C@@H](N=C([C@H](N=C([C@@H](N=C([C@@H](N=C([C@H](N=C2O)CC5=CNC6=CC=CC=C65)O)CC(=O)O)O)CC(=O)O)O)C7=CC=C(C=C7)O)O)CC(=O)O)O)O)[C@@H](C(=N)O)O)O)CCC(=O)O)O)C)O)O
• InChI: InChI=1S/C66H76N14O26/c1-3-8-44-54(106-44)65(103)77-43(27-81)61(99)79-50-28(2)105-66(104)42(20-31-25-69-36-12-7-5-10-34(31)36)76-57(95)37(17-18-46(84)85)71-64(102)52(53(92)55(67)93)78-45(83)26-70-56(94)39(21-47(86)87)75-63(101)51(29-13-15-32(82)16-14-29)80-60(98)41(23-49(90)91)73-59(97)40(22-48(88)89)72-58(96)38(74-62(50)100)19-30-24-68-35-11-6-4-9-33(30)35/h4-7,9-16,20,24-25,28,37-41,43-44,50-54,68-69,81-82,92H,3,8,17-19,21-23,26-27H2,1-2H3,(H2,67,93)(H,70,94)(H,71,102)(H,72,96)(H,73,97)(H,74,100)(H,75,101)(H,76,95)(H,77,103)(H,78,83)(H,79,99)(H,80,98)(H,84,85)(H,86,87)(H,88,89)(H,90,91)/b42-20-/t28-,37+,38-,39+,40+,41+,43+,44?,50+,51-,52-,53+,54?/m1/s1
• InChI Key: SLGCKWXDQZMUCF-SSNLTMHJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₇₆N₁₄O₂₆
• Molecular Weight: 1481.40 g/mol
• Exact Mass: 1480.50551858 g/mol
• Topological Polar Surface Area (TPSA): 683.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 4.84
• H-Bond Acceptor: 22
• H-Bond Donor: 22
• Rotatable Bonds: 22

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8877	88.77%
Caco-2	-	0.8567	85.67%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4490	44.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7968	79.68%
OATP1B3 inhibitior	+	0.9333	93.33%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7061	70.61%
BSEP inhibitior	+	0.9801	98.01%
P-glycoprotein inhibitior	+	0.7424	74.24%
P-glycoprotein substrate	+	0.8185	81.85%
CYP3A4 substrate	+	0.7493	74.93%
CYP2C9 substrate	-	0.6111	61.11%
CYP2D6 substrate	-	0.8626	86.26%
CYP3A4 inhibition	-	0.6472	64.72%
CYP2C9 inhibition	-	0.7840	78.40%
CYP2C19 inhibition	-	0.7311	73.11%
CYP2D6 inhibition	-	0.8672	86.72%
CYP1A2 inhibition	-	0.7723	77.23%
CYP2C8 inhibition	+	0.8477	84.77%
CYP inhibitory promiscuity	-	0.7016	70.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5708	57.08%
Eye corrosion	-	0.9824	98.24%
Eye irritation	-	0.8961	89.61%
Skin irritation	-	0.7619	76.19%
Skin corrosion	-	0.9212	92.12%
Ames mutagenesis	-	0.6791	67.91%
Human Ether-a-go-go-Related Gene inhibition	+	0.7337	73.37%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.6716	67.16%
skin sensitisation	-	0.8330	83.30%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7470	74.70%
Acute Oral Toxicity (c)	III	0.5721	57.21%
Estrogen receptor binding	+	0.5781	57.81%
Androgen receptor binding	+	0.7744	77.44%
Thyroid receptor binding	+	0.7715	77.15%
Glucocorticoid receptor binding	+	0.8104	81.04%
Aromatase binding	+	0.7424	74.24%
PPAR gamma	+	0.8131	81.31%
Honey bee toxicity	-	0.6297	62.97%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9087	90.87%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.61%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	99.54%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.25%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.41%	95.56%
CHEMBL2581	P07339	Cathepsin D	98.05%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.21%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	95.68%	91.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.58%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.24%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.37%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.13%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.91%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.53%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.11%	99.17%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	88.24%	97.64%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.09%	90.08%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	86.66%	97.31%
CHEMBL3310	Q96DB2	Histone deacetylase 11	85.56%	88.56%
CHEMBL255	P29275	Adenosine A2b receptor	84.99%	98.59%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.39%	94.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.04%	96.21%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.03%	95.56%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	80.52%	82.38%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.07%	92.62%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 102077146
• LOTUS: LTS0022216
• wikiData: Q105255301