Massetolide F

Details

• Internal ID: 95260c2c-d6f1-4ffc-902c-4b6e99d6527d
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (4R)-5-[[(3S,6R,9S,12R,15S,18R,21R)-6,12-bis(hydroxymethyl)-22-methyl-3,9,15-tris(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-18-propan-2-yl-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]amino]-4-[[(2S)-2-[[(3S)-3-hydroxydecanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid
• SMILES (Canonical): CCCCCCCC(CC(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NC1C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)C(C)C)CC(C)C)CO)CC(C)C)CO)CC(C)C)C)O
• SMILES (Isomeric): CCCCCCC[C@@H](CC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@@H]1C(OC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)C(C)C)CC(C)C)CO)CC(C)C)CO)CC(C)C)C)O
• InChI: InChI=1S/C54H95N9O16/c1-13-14-15-16-17-18-34(66)25-42(67)55-36(21-28(2)3)47(71)56-35(19-20-43(68)69)46(70)63-45-33(12)79-54(78)39(24-31(8)9)59-51(75)41(27-65)61-48(72)37(22-29(4)5)57-50(74)40(26-64)60-49(73)38(23-30(6)7)58-52(76)44(32(10)11)62-53(45)77/h28-41,44-45,64-66H,13-27H2,1-12H3,(H,55,67)(H,56,71)(H,57,74)(H,58,76)(H,59,75)(H,60,73)(H,61,72)(H,62,77)(H,63,70)(H,68,69)/t33?,34-,35+,36-,37-,38-,39-,40+,41+,44+,45+/m0/s1
• InChI Key: DSYOCLWRCTWQOY-KEARXTDGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₅N₉O₁₆
• Molecular Weight: 1126.40 g/mol
• Exact Mass: 1125.68967798 g/mol
• Topological Polar Surface Area (TPSA): 386.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 0.10
• H-Bond Acceptor: 15
• H-Bond Donor: 13
• Rotatable Bonds: 27

Synonyms

• (4R)-5-[[(3S,6R,9S,12R,15S,18R,21R)-6,12-bis(hydroxymethyl)-22-methyl-3,9,15-tris(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-18-propan-2-yl-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]amino]-4-[[(2S)-2-[[(3S)-3-hydroxydecanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid
• (4R)-4-(((2S)-2-(((3S)-1,3-dihydroxydecylidene)amino)-1-hydroxy-4-methylpentylidene)amino)-4-(((3S,6R,9S,12R,15S,18R,21R)-5,8,11,14,17,20-hexahydroxy-6,12-bis(hydroxymethyl)-22-methyl-3,9,15-tris(2-methylpropyl)-2-oxo-18-(propan-2-yl)-1-oxa-4,7,10,13,16,19-hexaazacyclodocosa-4,7,10,13,16,19-hexaen-21-yl)-C-hydroxycarbonimidoyl)butanoate
• (4R)-4-{[(2S)-2-{[(3S)-1,3-dihydroxydecylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-4-{[(3S,6R,9S,12R,15S,18R,21R)-5,8,11,14,17,20-hexahydroxy-6,12-bis(hydroxymethyl)-22-methyl-3,9,15-tris(2-methylpropyl)-2-oxo-18-(propan-2-yl)-1-oxa-4,7,10,13,16,19-hexaazacyclodocosa-4,7,10,13,16,19-hexaen-21-yl]-C-hydroxycarbonimidoyl}butanoate
• (4R)-5-(((3S,6R,9S,12R,15S,18R,21R)-6,12-bis(hydroxymethyl)-22-methyl-3,9,15-tris(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-18-propan-2-yl-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl)amino)-4-(((2S)-2-(((3S)-3-hydroxydecanoyl)amino)-4-methylpentanoyl)amino)-5-oxopentanoic acid
• (4R)-5-(((3S,6R,9S,12R,15S,18R,21R,22R)-6,12-bis(hydroxymethyl)-22-methyl-3,9,15-tris(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-18-propan-2-yl-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl)amino)-4-(((2S)-2-(((3R)-3-hydroxydecanoyl)amino)-4-methylpentanoyl)amino)-5-oxopentanoic acid
• (4R)-5-[[(3S,6R,9S,12R,15S,18R,21R,22R)-6,12-bis(hydroxymethyl)-22-methyl-3,9,15-tris(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-18-propan-2-yl-1-oxa-4,7,10,13,16,19-hexazacyclodocos-21-yl]amino]-4-[[(2S)-2-[[(3R)-3-hydroxydecanoyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid
• RefChem:155956
• 186409-64-3
• Mabetaetolide F
• SCHEMBL29678018
• CHEBI:202189

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5058	50.58%
Caco-2	-	0.8596	85.96%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5577	55.77%
OATP2B1 inhibitior	-	0.8631	86.31%
OATP1B1 inhibitior	+	0.8133	81.33%
OATP1B3 inhibitior	+	0.8899	88.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9275	92.75%
P-glycoprotein inhibitior	+	0.7387	73.87%
P-glycoprotein substrate	+	0.8722	87.22%
CYP3A4 substrate	+	0.6898	68.98%
CYP2C9 substrate	-	0.5928	59.28%
CYP2D6 substrate	-	0.8672	86.72%
CYP3A4 inhibition	-	0.6690	66.90%
CYP2C9 inhibition	-	0.9408	94.08%
CYP2C19 inhibition	-	0.9364	93.64%
CYP2D6 inhibition	-	0.9278	92.78%
CYP1A2 inhibition	-	0.9435	94.35%
CYP2C8 inhibition	+	0.5837	58.37%
CYP inhibitory promiscuity	-	0.9871	98.71%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6344	63.44%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.8967	89.67%
Skin irritation	-	0.7894	78.94%
Skin corrosion	-	0.9398	93.98%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3930	39.30%
Micronuclear	+	0.7600	76.00%
Hepatotoxicity	+	0.5397	53.97%
skin sensitisation	-	0.8786	87.86%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5160	51.60%
Acute Oral Toxicity (c)	III	0.6979	69.79%
Estrogen receptor binding	+	0.7544	75.44%
Androgen receptor binding	+	0.6673	66.73%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6227	62.27%
Aromatase binding	+	0.6604	66.04%
PPAR gamma	+	0.7571	75.71%
Honey bee toxicity	-	0.7916	79.16%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5865	58.65%
Fish aquatic toxicity	-	0.4210	42.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.83%	98.95%
CHEMBL3837	P07711	Cathepsin L	99.42%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	98.42%	99.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	98.16%	93.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	97.15%	92.08%
CHEMBL230	P35354	Cyclooxygenase-2	96.87%	89.63%
CHEMBL4801	P29466	Caspase-1	96.13%	96.85%
CHEMBL3468	P55210	Caspase-7	95.12%	95.68%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	94.83%	96.47%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	94.50%	96.90%
CHEMBL2094135	Q96BI3	Gamma-secretase	94.40%	98.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.18%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.17%	96.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.79%	90.08%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	92.77%	91.81%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	91.02%	97.29%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	90.83%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	90.75%	90.17%
CHEMBL1255126	O15151	Protein Mdm4	90.71%	90.20%
CHEMBL4227	P25090	Lipoxin A4 receptor	90.45%	100.00%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	90.44%	95.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.26%	89.50%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	87.95%	96.11%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.92%	97.14%
CHEMBL2334	P42574	Caspase-3	87.24%	98.25%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.07%	90.71%
CHEMBL236	P41143	Delta opioid receptor	86.99%	99.35%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	86.94%	97.23%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	86.81%	92.32%
CHEMBL5255	O00206	Toll-like receptor 4	86.77%	92.50%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	86.10%	98.33%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	85.88%	97.64%
CHEMBL2514	O95665	Neurotensin receptor 2	85.54%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.48%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.63%	99.23%
CHEMBL1949	P62937	Cyclophilin A	84.53%	98.57%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.50%	95.56%
CHEMBL3776	Q14790	Caspase-8	83.15%	97.06%
CHEMBL4588	P22894	Matrix metalloproteinase 8	82.74%	94.66%
CHEMBL299	P17252	Protein kinase C alpha	82.65%	98.03%
CHEMBL237	P41145	Kappa opioid receptor	82.41%	98.10%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.30%	100.00%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	81.86%	90.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.83%	97.09%
CHEMBL4374	Q9Y5X4	Photoreceptor-specific nuclear receptor	81.62%	85.00%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	81.45%	97.50%
CHEMBL1801	P00747	Plasminogen	81.23%	92.44%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.22%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.17%	93.00%

Plants that contains it

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Cross-Links

• PubChem: 11804329
• LOTUS: LTS0039577
• wikiData: Q77369746