Xenoamicin C

Details

• Internal ID: d46cc099-2df3-46d1-a599-bb87103b37c8
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2S)-1-butanoyl-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S,3R)-1-[[(7R,10S,13R,16S,19R,20R,23S,26R)-13-[(2R)-butan-2-yl]-7,20-dimethyl-2,6,9,12,15,18,22,25-octaoxo-10,16,23-tri(propan-2-yl)-21-oxa-1,5,8,11,14,17,24-heptazabicyclo[24.3.0]nonacosan-19-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
• InChI: InChI=1S/C65H111N13O15/c1-19-24-45(79)77-29-22-25-43(77)57(84)67-40(17)55(82)70-48(34(8)9)60(87)69-42(31-32(4)5)56(83)74-51(37(14)20-2)63(90)76-53-41(18)93-65(92)50(36(12)13)73-58(85)44-26-23-30-78(44)46(80)27-28-66-54(81)39(16)68-59(86)47(33(6)7)71-62(89)52(38(15)21-3)75-61(88)49(35(10)11)72-64(53)91/h32-44,47-53H,19-31H2,1-18H3,(H,66,81)(H,67,84)(H,68,86)(H,69,87)(H,70,82)(H,71,89)(H,72,91)(H,73,85)(H,74,83)(H,75,88)(H,76,90)/t37-,38-,39-,40-,41-,42-,43+,44-,47+,48+,49+,50+,51+,52-,53-/m1/s1
• InChI Key: RCNSZSLZDQBOEM-YXEJCLQBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₅H₁₁₁N₁₃O₁₅
• Molecular Weight: 1314.70 g/mol
• Exact Mass: 1313.83225988 g/mol
• Topological Polar Surface Area (TPSA): 387.00 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 0.87
• H-Bond Acceptor: 15
• H-Bond Donor: 11
• Rotatable Bonds: 22

Synonyms

• RefChem:195251
• (2S)-1-butanoyl-N-((2R)-1-(((2S)-1-(((2R)-1-(((2S,3R)-1-(((7R,10S,13R,16S,19R,20R,23S,26R)-13-((2R)-butan-2-yl)-7,20-dimethyl-2,6,9,12,15,18,22,25-octaoxo-10,16,23-tri(propan-2-yl)-21-oxa-1,5,8,11,14,17,24-heptazabicyclo(24.3.0)nonacosan-19-yl)amino)-3-methyl-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)amino)-1-oxopropan-2-yl)pyrrolidine-2-carboxamide
• (2S)-1-butanoyl-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S,3R)-1-[[(7R,10S,13R,16S,19R,20R,23S,26R)-13-[(2R)-butan-2-yl]-7,20-dimethyl-2,6,9,12,15,18,22,25-octaoxo-10,16,23-tri(propan-2-yl)-21-oxa-1,5,8,11,14,17,24-heptazabicyclo[24.3.0]nonacosan-19-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
• (2S,3R)-N-((3S,6R,7R,10S,13R,16S,19R,28AR)-13-((2R)-butan-2-yl)-1,8,11,14,17,20-hexahydroxy-6,19-dimethyl-4,24-dioxo-3,10,16-tris(propan-2-yl)-3H,4H,6H,7H,10H,13H,16H,19H,22H,23H,24H,26H,27H,28H,28ah-pyrrolo(2,1-F)1-oxa-4,7,11,14,17,20,23-heptaazacyclohexacosan-7-yl)-2-(((2R)-2-(((2S)-2-(((2R)-2-((((2S)-1-butanoylpyrrolidin-2-yl)(hydroxy)methylidene)amino)-1-hydroxypropylidene)amino)-1-hydroxy-3-methylbutylidene)amino)-1-hydroxy-4-methylpentylidene)amino)-3-methylpentanimidate
• (2S,3R)-N-[(3S,6R,7R,10S,13R,16S,19R,28AR)-13-[(2R)-butan-2-yl]-1,8,11,14,17,20-hexahydroxy-6,19-dimethyl-4,24-dioxo-3,10,16-tris(propan-2-yl)-3H,4H,6H,7H,10H,13H,16H,19H,22H,23H,24H,26H,27H,28H,28ah-pyrrolo[2,1-F]1-oxa-4,7,11,14,17,20,23-heptaazacyclohexacosan-7-yl]-2-{[(2R)-2-{[(2S)-2-{[(2R)-2-({[(2S)-1-butanoylpyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-methylpentanimidate
• CHEBI:220983

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6442	64.42%
Caco-2	-	0.8583	85.83%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Lysosomes	0.6470	64.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8171	81.71%
OATP1B3 inhibitior	+	0.9186	91.86%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9797	97.97%
P-glycoprotein inhibitior	+	0.7433	74.33%
P-glycoprotein substrate	+	0.8843	88.43%
CYP3A4 substrate	+	0.7363	73.63%
CYP2C9 substrate	-	0.7646	76.46%
CYP2D6 substrate	-	0.8398	83.98%
CYP3A4 inhibition	-	0.9062	90.62%
CYP2C9 inhibition	-	0.9039	90.39%
CYP2C19 inhibition	-	0.8759	87.59%
CYP2D6 inhibition	-	0.9160	91.60%
CYP1A2 inhibition	-	0.9368	93.68%
CYP2C8 inhibition	+	0.7354	73.54%
CYP inhibitory promiscuity	-	0.9735	97.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5822	58.22%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.7923	79.23%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7293	72.93%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	+	0.6894	68.94%
skin sensitisation	-	0.8866	88.66%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6183	61.83%
Acute Oral Toxicity (c)	III	0.6252	62.52%
Estrogen receptor binding	+	0.7245	72.45%
Androgen receptor binding	+	0.7403	74.03%
Thyroid receptor binding	+	0.5693	56.93%
Glucocorticoid receptor binding	+	0.7190	71.90%
Aromatase binding	+	0.7143	71.43%
PPAR gamma	+	0.7800	78.00%
Honey bee toxicity	-	0.6873	68.73%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.7204	72.04%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3837	P07711	Cathepsin L	99.92%	96.61%
CHEMBL2581	P07339	Cathepsin D	99.88%	98.95%
CHEMBL333	P08253	Matrix metalloproteinase-2	99.07%	96.31%
CHEMBL255	P29275	Adenosine A2b receptor	98.34%	98.59%
CHEMBL4801	P29466	Caspase-1	98.29%	96.85%
CHEMBL3468	P55210	Caspase-7	98.25%	95.68%
CHEMBL5103	Q969S8	Histone deacetylase 10	98.22%	90.08%
CHEMBL4588	P22894	Matrix metalloproteinase 8	97.57%	94.66%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.56%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.39%	97.09%
CHEMBL321	P14780	Matrix metalloproteinase 9	97.13%	92.12%
CHEMBL3359	P21462	Formyl peptide receptor 1	96.79%	93.56%
CHEMBL4072	P07858	Cathepsin B	96.61%	93.67%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	95.81%	98.33%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	94.94%	92.38%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	94.34%	97.64%
CHEMBL283	P08254	Matrix metalloproteinase 3	93.29%	97.29%
CHEMBL230	P35354	Cyclooxygenase-2	92.66%	89.63%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.62%	97.25%
CHEMBL332	P03956	Matrix metalloproteinase-1	91.62%	94.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.48%	90.71%
CHEMBL4073	P09237	Matrix metalloproteinase 7	91.16%	97.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.05%	93.03%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	90.84%	97.50%
CHEMBL2514	O95665	Neurotensin receptor 2	90.65%	100.00%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	90.46%	98.24%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.18%	91.11%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.01%	96.47%
CHEMBL5203	P33316	dUTP pyrophosphatase	89.88%	99.18%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.79%	99.23%
CHEMBL3691	Q13822	Autotaxin	89.63%	96.39%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.59%	97.14%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	88.35%	95.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.87%	100.00%
CHEMBL2094135	Q96BI3	Gamma-secretase	87.76%	98.05%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.66%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.54%	85.14%
CHEMBL217	P14416	Dopamine D2 receptor	86.73%	95.62%
CHEMBL3310	Q96DB2	Histone deacetylase 11	86.58%	88.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.44%	94.33%
CHEMBL228	P31645	Serotonin transporter	86.29%	95.51%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.21%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.12%	82.38%
CHEMBL237	P41145	Kappa opioid receptor	86.11%	98.10%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.01%	100.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.74%	90.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.44%	99.17%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	85.29%	88.42%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	85.24%	82.50%
CHEMBL4018	P49146	Neuropeptide Y receptor type 2	84.97%	98.94%
CHEMBL340	P08684	Cytochrome P450 3A4	84.48%	91.19%
CHEMBL226	P30542	Adenosine A1 receptor	84.45%	95.93%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.06%	93.10%
CHEMBL4123	P30989	Neurotensin receptor 1	83.47%	96.67%
CHEMBL221	P23219	Cyclooxygenase-1	83.24%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.16%	95.56%
CHEMBL259	P32245	Melanocortin receptor 4	82.50%	95.38%
CHEMBL3776	Q14790	Caspase-8	81.89%	97.06%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	81.13%	97.86%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.80%	89.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.42%	95.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	80.12%	95.71%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	80.11%	90.71%

Plants that contains it

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Cross-Links

• PubChem: 145720560
• LOTUS: LTS0159729
• wikiData: Q105233824