Actinonin

Details

• Internal ID: b964cf81-1d4e-476a-b45f-b04237ccea39
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > N-acyl-alpha amino acids and derivatives
• IUPAC Name: (2R)-N'-hydroxy-N-[(2S)-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-pentylbutanediamide
• InChI: InChI=1S/C19H35N3O5/c1-4-5-6-8-14(11-16(24)21-27)18(25)20-17(13(2)3)19(26)22-10-7-9-15(22)12-23/h13-15,17,23,27H,4-12H2,1-3H3,(H,20,25)(H,21,24)/t14-,15+,17+/m1/s1
• InChI Key: XJLATMLVMSFZBN-VYDXJSESSA-N
• Popularity: 404 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₅N₃O₅
• Molecular Weight: 385.50 g/mol
• Exact Mass: 385.25767123 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.20
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• Actinonine
• 13434-13-4
• P18SPA8N0K
• CHEMBL308333
• (R)-N4-hydroxy-N1-((S)-1-((S)-2-(hydroxymethyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-pentylsuccinamide
• Octanohydroxamic acid, 3-((1-((2-(hydroxymethyl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)carbamoyl)-
• (-)-actinonin
• BB2
• SR-01000075681
• UNII-P18SPA8N0K
• 3g5k
• 3m6p
• 3m6q
• 3m6r
• 3pn4
• 4dr9
• 4je7
• Spectrum2_000628
• Spectrum3_000680
• Spectrum4_001932
• Spectrum5_000728
• Lopac0_000010
• BSPBio_002379
• KBioGR_002305
• DivK1c_001024
• SCHEMBL279450
• SPBio_000596
• HMS503M09
• KBio1_001024
• KBio3_001599
• DTXSID70928580
• NINDS_001024
• HMS3260A21
• (2R)-2-[2-(hydroxyamino)-2-oxo-ethyl]-N-[(1S)-1-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-2-methyl-propyl]heptanamide
• N*4*-Hydroxy-N*1*-[1-(2-hydroxymethyl-pyrrolidine-1-carbonyl)-2-methyl-propyl]-2-pentyl-succinamide
• Tox21_500010
• BDBM50089194
• CCG-38543
• HB3737
• AKOS015894413
• DB04310
• LP00010
• SDCCGSBI-0049999.P004
• IDI1_001024
• NCGC00093535-01
• NCGC00093535-02
• NCGC00093535-03
• NCGC00093535-04
• NCGC00093535-07
• NCGC00260695-01
• (2R)-N'-hydroxy-N-[(2S)-1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-pentylbutanediamide
• 2-[(FORMYL-HYDROXY-AMINO)-METHYL]-HEPTANOIC ACID [1-(2-HYDROXYMETHYL-PYRROLIDINE-1-CARBONYL)-2-METHYL-PROPYL]-AMIDE
• Butanediamide, N4-hydroxy-N1-(1-((2-(hydroxymethyl)-1-pyrrolidinyl)carbonyl)-2-methylpropyl)-2-pentyl-, stereoisomer
• HY-113952
• CS-0064758
• EU-0100010
• A 6671
• F82262
• Q4676979
• SR-01000075681-1
• SR-01000075681-5
• Actinonin in combination with isoniazid and rifampicin
• BRD-K24621118-001-02-5
• BRD-K24621118-001-03-3
• (2R)-N~4~-hydroxy-N~1~-[(1S)-1-{[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]carbonyl}-2-methylpropyl]-2-pentylbutanediamide
• (2R)-N4-HYDROXY-N1-((2S)-1-((2S)-2-(HYDROXYMETHYL)PYRROLIDIN-1-YL)-3-METHYL-1-OXOBUTAN-2-YL)-2-PENTYLBUTANEDIAMIDE
• (R)-N*4*-Hydroxy-N*1*-[(S)-1-((S)-2-hydroxymethyl-pyrrolidine-1-carbonyl)-2-methyl-propyl]-2-pentyl-succinamide
• N*4*-Hydroxy-N*1*-[(S)-1-((S)-2-hydroxymethyl-pyrrolidine-1-carbonyl)-2-methyl-propyl]-2-(R)-pentyl-succinamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8810	88.10%
Caco-2	-	0.7482	74.82%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4753	47.53%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.9107	91.07%
OATP1B3 inhibitior	+	0.9340	93.40%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8495	84.95%
P-glycoprotein inhibitior	-	0.8033	80.33%
P-glycoprotein substrate	+	0.7001	70.01%
CYP3A4 substrate	+	0.5901	59.01%
CYP2C9 substrate	-	0.7919	79.19%
CYP2D6 substrate	-	0.8479	84.79%
CYP3A4 inhibition	-	0.8308	83.08%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8657	86.57%
CYP inhibitory promiscuity	-	0.9856	98.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6100	61.00%
Carcinogenicity (trinary)	Non-required	0.5374	53.74%
Eye corrosion	-	0.9793	97.93%
Eye irritation	-	0.9828	98.28%
Skin irritation	-	0.7709	77.09%
Skin corrosion	-	0.9114	91.14%
Ames mutagenesis	-	0.7037	70.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.7945	79.45%
Micronuclear	+	0.6400	64.00%
Hepatotoxicity	+	0.6513	65.13%
skin sensitisation	-	0.8608	86.08%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6905	69.05%
Acute Oral Toxicity (c)	III	0.6369	63.69%
Estrogen receptor binding	+	0.5907	59.07%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.4879	48.79%
Glucocorticoid receptor binding	+	0.6231	62.31%
Aromatase binding	-	0.4836	48.36%
PPAR gamma	-	0.5124	51.24%
Honey bee toxicity	-	0.9452	94.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5376	53.76%
Fish aquatic toxicity	+	0.7349	73.49%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	1 nM	Potency	via Super-PRED
CHEMBL4588	P22894	Matrix metalloproteinase 8	190 nM	Ki	via Super-PRED
CHEMBL321	P14780	Matrix metalloproteinase 9	330 nM	Ki	via Super-PRED
CHEMBL332	P03956	Matrix metalloproteinase-1	300 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL283	P08254	Matrix metalloproteinase 3	99.82%	97.29%
CHEMBL2581	P07339	Cathepsin D	99.50%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.48%	97.25%
CHEMBL333	P08253	Matrix metalloproteinase-2	99.46%	96.31%
CHEMBL4073	P09237	Matrix metalloproteinase 7	97.97%	97.56%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	95.70%	98.33%
CHEMBL4801	P29466	Caspase-1	95.54%	96.85%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.45%	96.47%
CHEMBL4393	P39900	Matrix metalloproteinase 12	94.54%	92.22%
CHEMBL3359	P21462	Formyl peptide receptor 1	94.45%	93.56%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	93.92%	92.86%
CHEMBL1865	Q9UBN7	Histone deacetylase 6	93.82%	97.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.58%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.56%	96.09%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	93.40%	91.81%
CHEMBL4072	P07858	Cathepsin B	93.05%	93.67%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.62%	96.61%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.51%	90.08%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	91.94%	100.00%
CHEMBL237	P41145	Kappa opioid receptor	91.71%	98.10%
CHEMBL2514	O95665	Neurotensin receptor 2	91.55%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	91.46%	97.47%
CHEMBL3437	Q16853	Amine oxidase, copper containing	90.69%	94.00%
CHEMBL3468	P55210	Caspase-7	90.61%	95.68%
CHEMBL340	P08684	Cytochrome P450 3A4	90.60%	91.19%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	90.58%	95.50%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	90.58%	96.03%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.13%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.84%	99.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.59%	97.29%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.68%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.36%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.18%	90.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.77%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.76%	94.33%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	87.51%	97.50%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	87.23%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	86.95%	92.50%
CHEMBL3691	Q13822	Autotaxin	86.82%	96.39%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	86.19%	95.52%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	85.83%	97.86%
CHEMBL3776	Q14790	Caspase-8	85.41%	97.06%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.13%	91.24%
CHEMBL1978	P11511	Cytochrome P450 19A1	85.13%	91.76%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.57%	100.00%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	84.54%	95.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.48%	97.21%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	84.05%	97.64%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.94%	96.90%
CHEMBL4040	P28482	MAP kinase ERK2	82.92%	83.82%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	82.77%	96.00%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	82.15%	98.24%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.62%	89.50%
CHEMBL5203	P33316	dUTP pyrophosphatase	81.55%	99.18%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.25%	96.38%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.11%	90.24%
CHEMBL221	P23219	Cyclooxygenase-1	80.66%	90.17%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.54%	92.88%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	80.46%	90.24%
CHEMBL3837	P07711	Cathepsin L	80.28%	96.61%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.01%	93.03%

Plants that contains it

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Cross-Links

• PubChem: 443600
• LOTUS: LTS0062692
• wikiData: Q4676979