(2S,3R)-2-amino-3-hydroxy-4-methylpentanoic acid

Details

• Internal ID: be509d49-42bd-4612-9fae-9b390ea55aa8
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Leucine and derivatives
• IUPAC Name: (2S,3R)-2-amino-3-hydroxy-4-methylpentanoic acid
• SMILES (Canonical): CC(C)C(C(C(=O)O)N)O
• SMILES (Isomeric): CC(C)[C@H]([C@@H](C(=O)O)N)O
• InChI: InChI=1S/C6H13NO3/c1-3(2)5(8)4(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t4-,5+/m0/s1
• InChI Key: ZAYJDMWJYCTABM-CRCLSJGQSA-N
• Popularity: 11 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 147.17 g/mol
• Exact Mass: 147.08954328 g/mol
• Topological Polar Surface Area (TPSA): 83.60 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -0.58
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• (2S,3R)-2-amino-3-hydroxy-4-methylpentanoic acid
• (2S,3R)-(+)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID
• L-Leucine, 3-hydroxy-, (3R)-
• beta-Hydroxyleucine
• (2S,3R)-2-Amino-3-hydroxy-4-methyl-pentanoic acid
• L(+)-threo-3-Hydroxyleucine
• MFCD00142983
• (2s,3r)-beta-hydroxyleucine
• SCHEMBL2032146
• ZAYJDMWJYCTABM-CRCLSJGQSA-N
• AKOS006342683
• AKOS015841478
• AM84304
• AS-59491
• (2S,3R)-2-amino-3-hydroxy-4-methylpentanoicacid
• A897147
• Q27461121
• (2S*,3R*)-2-amino-3-hydroxy-4-methyl-pentanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9579	95.79%
Caco-2	-	0.9383	93.83%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Lysosomes	0.5134	51.34%
OATP2B1 inhibitior	-	0.8455	84.55%
OATP1B1 inhibitior	+	0.9723	97.23%
OATP1B3 inhibitior	+	0.9590	95.90%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9399	93.99%
P-glycoprotein inhibitior	-	0.9744	97.44%
P-glycoprotein substrate	-	0.9809	98.09%
CYP3A4 substrate	-	0.7858	78.58%
CYP2C9 substrate	+	0.6040	60.40%
CYP2D6 substrate	-	0.7882	78.82%
CYP3A4 inhibition	-	0.8547	85.47%
CYP2C9 inhibition	-	0.9036	90.36%
CYP2C19 inhibition	-	0.9109	91.09%
CYP2D6 inhibition	-	0.9378	93.78%
CYP1A2 inhibition	-	0.7866	78.66%
CYP2C8 inhibition	-	0.9963	99.63%
CYP inhibitory promiscuity	-	0.9766	97.66%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6249	62.49%
Carcinogenicity (trinary)	Non-required	0.7347	73.47%
Eye corrosion	-	0.9798	97.98%
Eye irritation	-	0.7079	70.79%
Skin irritation	-	0.7593	75.93%
Skin corrosion	-	0.8959	89.59%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8764	87.64%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.9726	97.26%
Respiratory toxicity	-	0.7889	78.89%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	-	0.5774	57.74%
Acute Oral Toxicity (c)	III	0.6824	68.24%
Estrogen receptor binding	-	0.9057	90.57%
Androgen receptor binding	-	0.8898	88.98%
Thyroid receptor binding	-	0.7946	79.46%
Glucocorticoid receptor binding	-	0.8661	86.61%
Aromatase binding	-	0.9000	90.00%
PPAR gamma	-	0.6809	68.09%
Honey bee toxicity	-	0.9695	96.95%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.9900	99.00%
Fish aquatic toxicity	-	0.8857	88.57%

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	97.12%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.46%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.30%	98.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.42%	93.56%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.05%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.64%	85.14%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	81.62%	95.58%

Plants that contains it

• Chaenomeles sinensis

Cross-Links

• PubChem: 6994743
• NPASS: NPC168081