(3R)-3-[(3Z,6S,9R,15S,18R,21S,24S,27R,30S,31R)-15,21,24-tris(carboxymethyl)-30-[[(2S)-1,3-dihydroxy-2-(1-hydroxybutylideneamino)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]butanoic acid

Details

• Internal ID: 3eb91c55-1c91-4596-86ce-9dda4e06eafd
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3R)-3-[(3Z,6S,9R,15S,18R,21S,24S,27R,30S,31R)-15,21,24-tris(carboxymethyl)-30-[[(2S)-1,3-dihydroxy-2-(1-hydroxybutylideneamino)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]butanoic acid
• SMILES (Canonical): CCCC(=NC(CO)C(=NC1C(OC(=O)C(=CC2=CNC3=CC=CC=C32)N=C(C(N=C(C(N=C(CN=C(C(N=C(C(N=C(C(N=C(C(N=C(C(N=C1O)CC4=CNC5=CC=CC=C54)O)CC(=O)O)O)CC(=O)O)O)C6=CC=C(C=C6)O)O)CC(=O)O)O)O)C(C(=N)O)O)O)C(C)CC(=O)O)O)C)O)O
• SMILES (Isomeric): CCCC(=N[C@@H](CO)C(=N[C@H]1[C@H](OC(=O)/C(=C/C2=CNC3=CC=CC=C32)/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=C1O)CC4=CNC5=CC=CC=C54)O)CC(=O)O)O)CC(=O)O)O)C6=CC=C(C=C6)O)O)CC(=O)O)O)O)[C@@H](C(=N)O)O)O)[C@H](C)CC(=O)O)O)C)O)O
• InChI: InChI=1S/C65H76N14O25/c1-4-9-44(82)70-43(27-80)60(98)78-51-29(3)104-65(103)42(20-32-25-68-37-13-8-6-11-35(32)37)75-61(99)50(28(2)18-46(84)85)77-64(102)53(54(92)55(66)93)76-45(83)26-69-56(94)39(21-47(86)87)74-63(101)52(30-14-16-33(81)17-15-30)79-59(97)41(23-49(90)91)72-58(96)40(22-48(88)89)71-57(95)38(73-62(51)100)19-31-24-67-36-12-7-5-10-34(31)36/h5-8,10-17,20,24-25,28-29,38-41,43,50-54,67-68,80-81,92H,4,9,18-19,21-23,26-27H2,1-3H3,(H2,66,93)(H,69,94)(H,70,82)(H,71,95)(H,72,96)(H,73,100)(H,74,101)(H,75,99)(H,76,83)(H,77,102)(H,78,98)(H,79,97)(H,84,85)(H,86,87)(H,88,89)(H,90,91)/b42-20-/t28-,29-,38-,39+,40+,41+,43+,50+,51+,52-,53-,54+/m1/s1
• InChI Key: CVOAOKXASHELBI-BZUDXOATSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₅H₇₆N₁₄O₂₅
• Molecular Weight: 1453.40 g/mol
• Exact Mass: 1452.51060397 g/mol
• Topological Polar Surface Area (TPSA): 670.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 5.32
• H-Bond Acceptor: 21
• H-Bond Donor: 22
• Rotatable Bonds: 21

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8763	87.63%
Caco-2	-	0.8568	85.68%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4261	42.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8019	80.19%
OATP1B3 inhibitior	+	0.9293	92.93%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7311	73.11%
BSEP inhibitior	+	0.9720	97.20%
P-glycoprotein inhibitior	+	0.7423	74.23%
P-glycoprotein substrate	+	0.8235	82.35%
CYP3A4 substrate	+	0.7470	74.70%
CYP2C9 substrate	-	0.5974	59.74%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.6309	63.09%
CYP2C9 inhibition	-	0.8075	80.75%
CYP2C19 inhibition	-	0.7830	78.30%
CYP2D6 inhibition	-	0.8773	87.73%
CYP1A2 inhibition	-	0.8224	82.24%
CYP2C8 inhibition	+	0.8307	83.07%
CYP inhibitory promiscuity	-	0.6889	68.89%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5830	58.30%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.7637	76.37%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	-	0.6537	65.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7383	73.83%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.7042	70.42%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7546	75.46%
Acute Oral Toxicity (c)	III	0.5926	59.26%
Estrogen receptor binding	+	0.6110	61.10%
Androgen receptor binding	+	0.7763	77.63%
Thyroid receptor binding	+	0.7594	75.94%
Glucocorticoid receptor binding	+	0.7999	79.99%
Aromatase binding	+	0.7188	71.88%
PPAR gamma	+	0.8049	80.49%
Honey bee toxicity	-	0.6238	62.38%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9066	90.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.69%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.41%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.66%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.95%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.05%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.56%	94.45%
CHEMBL5103	Q969S8	Histone deacetylase 10	95.54%	90.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.50%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.85%	97.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	92.27%	91.71%
CHEMBL3310	Q96DB2	Histone deacetylase 11	91.95%	88.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.51%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	90.13%	93.10%
CHEMBL3401	O75469	Pregnane X receptor	89.45%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.93%	99.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.71%	94.62%
CHEMBL1951	P21397	Monoamine oxidase A	85.93%	91.49%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	85.47%	97.64%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.49%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.75%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.68%	92.62%
CHEMBL4105838	Q96GG9	DCN1-like protein 1	81.51%	95.00%
CHEMBL2000	P03952	Plasma kallikrein	81.27%	93.92%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	80.33%	95.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.17%	96.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163187490
• LOTUS: LTS0145259
• wikiData: Q104970905