Ubenimex

Details

• Internal ID: d709a322-71d2-47b6-977d-9e3b118491b5
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid
• InChI: InChI=1S/C16H24N2O4/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22)/t12-,13+,14+/m1/s1
• InChI Key: VGGGPCQERPFHOB-RDBSUJKOSA-N
• Popularity: 2,689 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄N₂O₄
• Molecular Weight: 308.37 g/mol
• Exact Mass: 308.17360725 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): 0.53
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

• Ubenimex
• 58970-76-6
• (S)-2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoic acid
• NK-421
• (-)-bestatin
• Ubenimex (Bestatin)
• N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine
• (2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid
• CHEMBL29292
• N-[(2S,3R)-3-Amino-2-hydroxy-1-oxo-4-phenylbutyl]-L-leucine
• 58970-76-6 (free base)
• I0J33N5627
• NSC-265489
• ((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)-L-leucine
• L-Leucine, N-[(2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-
• MFCD00083262
• 2-(3-AMINO-2-HYDROXY-4-PHENYL-BUTYRYLAMINO)-4-METHYL-PENTANOIC ACID
• Ubenimexum [Latin]
• Ubenimexum
• Ubenimex [INN:JAN]
• SMR000059165
• (2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid
• EINECS 261-529-2
• NK 421
• NSC 265489
• BRN 4704312
• Ubestatin
• Ubenimex, solid
• L-LEUCINE, N-((2S,3R)-3-AMINO-2-HYDROXY-1-OXO-4-PHENYLBUTYL)-
• UNII-I0J33N5627
• 1txr
• Ubenimex- Bio-X
• Ubenimex(Bestatin)
• Ubenimex, Bestatin
• Ubenimex,(S)
• 3-(R)-Amino-2-(S)-hydroxy-4-phenylbutanoyl-(S)-leucine
• UBENIMEX [INN]
• UBENIMEX [JAN]
• UBENIMEX [MI]
• UBENIMEX [MART.]
• UBENIMEX [WHO-DD]
• SCHEMBL7944
• (3-Amino-2-hydroxy-4-phenylbutanoyl)-L-leucine
• Lopac0_000214
• BSPBio_001553
• KBioGR_000273
• KBioSS_000273
• MLS000028649
• MLS001424177
• MLS006010137
• BCBcMAP01_000178
• BDBM23971
• KBio2_000273
• KBio2_002841
• KBio2_005409
• KBio3_000545
• KBio3_000546
• VGGGPCQERPFHOB-RDBSUJKOSA-N
• Bio2_000273
• Bio2_000753
• HMS1361N15
• HMS1791N15
• HMS1989N15
• HMS2052A03
• HMS2232H13
• HMS3268O06
• HMS3402N15
• HMS3412N16
• HMS3676N16
• HMS3715B20
• (-)-N-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl)-L-leucine
• (S-(R*,S*))-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucine
• EX-A1292
• HY-B0134
• BDBM50367209
• NSC779839
• s1591
• AKOS016339610
• L-Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-, (S-(R*,S*))-
• CCG-101071
• CS-1910
• DB03424
• KS-5207
• NC00321
• NSC-779839
• SDCCGSBI-0050202.P003
• IDI1_034023
• SMP1_000030
• NCGC00025323-01
• NCGC00025323-02
• NCGC00025323-03
• NCGC00025323-04
• NCGC00025323-05
• NCGC00025323-06
• NCGC00025323-08
• NCGC00025323-14
• BU164499
• BCP0726000308
• U0111
• AB00698345_05
• EN300-7388593
• A832093
• SR-01000075724-3
• W-105351
• [(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-Leu
• BRD-K59574735-001-02-7
• BRD-K59574735-001-05-0
• Q10909912
• Z2242062173
• N-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine
• N-((2S,3R)-3-AMINO-2-HYDROXY-4-PHENYLBUTANOYL)-LEUCINE
• N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine, 97%
• (2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic acid
• (S)-2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoicacid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5802	58.02%
Caco-2	-	0.7687	76.87%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6785	67.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9216	92.16%
OATP1B3 inhibitior	+	0.9380	93.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.7647	76.47%
P-glycoprotein inhibitior	-	0.8801	88.01%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	-	0.5674	56.74%
CYP2C9 substrate	+	0.5844	58.44%
CYP2D6 substrate	-	0.7251	72.51%
CYP3A4 inhibition	-	0.8869	88.69%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	-	0.9068	90.68%
CYP2C8 inhibition	-	0.9399	93.99%
CYP inhibitory promiscuity	-	0.9469	94.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7418	74.18%
Carcinogenicity (trinary)	Non-required	0.7534	75.34%
Eye corrosion	-	0.9954	99.54%
Eye irritation	-	0.9866	98.66%
Skin irritation	-	0.8502	85.02%
Skin corrosion	-	0.9658	96.58%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5194	51.94%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.5661	56.61%
skin sensitisation	-	0.8988	89.88%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7960	79.60%
Acute Oral Toxicity (c)	III	0.5882	58.82%
Estrogen receptor binding	+	0.5584	55.84%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.7185	71.85%
Glucocorticoid receptor binding	+	0.8971	89.71%
Aromatase binding	+	0.5483	54.83%
PPAR gamma	-	0.6452	64.52%
Honey bee toxicity	-	0.9517	95.17%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.7016	70.16%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4618	P09960	Leukotriene A4 hydrolase	266 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.51%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	99.41%	90.17%
CHEMBL3837	P07711	Cathepsin L	94.36%	96.61%
CHEMBL1255126	O15151	Protein Mdm4	93.96%	90.20%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.72%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.04%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.85%	93.56%
CHEMBL4040	P28482	MAP kinase ERK2	91.60%	83.82%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.38%	99.17%
CHEMBL2095164	P49354	Geranylgeranyl transferase type I	88.94%	92.80%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.99%	100.00%
CHEMBL1907	P15144	Aminopeptidase N	87.53%	93.31%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.70%	95.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.90%	91.11%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.24%	100.00%
CHEMBL5028	O14672	ADAM10	81.01%	97.50%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.57%	98.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 72172
• LOTUS: LTS0225160
• wikiData: Q104984225