(2S,3S,4R)-2-Amino-3-methyl-4-hydroxyvaleric acid

Details

• Internal ID: b136746e-dc24-400a-8ecf-15951e993771
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Isoleucine and derivatives
• IUPAC Name: (2S,3S,4R)-2-amino-4-hydroxy-3-methylpentanoic acid
• SMILES (Canonical): CC(C(C)O)C(C(=O)O)N
• SMILES (Isomeric): C[C@H]([C@@H](C)O)[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4-,5+/m1/s1
• InChI Key: OSCCDBFHNMXNME-WDCZJNDASA-N
• Popularity: 7 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: -2.80
• Atomic LogP (AlogP): -0.58
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• SCHEMBL598327
• AKOS006337468
• 2-Amino-2,3,5-trideoxy-3-methyl-D-xylonic Acid
• (2S,3S,4R)-2-Amino-3-methyl-4-hydroxyvaleric acid
• (2S,3R,4S)-4-Hydroxyisoleucine Major Isomer and (2R,3R,4S)-4-Hydroxyisoleucine Minor Isomer

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9480	94.80%
Caco-2	-	0.9259	92.59%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Lysosomes	0.5000	50.00%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.9658	96.58%
OATP1B3 inhibitior	+	0.9561	95.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9388	93.88%
P-glycoprotein inhibitior	-	0.9832	98.32%
P-glycoprotein substrate	-	0.9793	97.93%
CYP3A4 substrate	-	0.7783	77.83%
CYP2C9 substrate	+	0.6045	60.45%
CYP2D6 substrate	-	0.8074	80.74%
CYP3A4 inhibition	-	0.9227	92.27%
CYP2C9 inhibition	-	0.9041	90.41%
CYP2C19 inhibition	-	0.9436	94.36%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.8645	86.45%
CYP2C8 inhibition	-	0.9941	99.41%
CYP inhibitory promiscuity	-	0.9853	98.53%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.6249	62.49%
Carcinogenicity (trinary)	Non-required	0.7302	73.02%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.9240	92.40%
Skin irritation	-	0.7597	75.97%
Skin corrosion	-	0.9165	91.65%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8836	88.36%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.9611	96.11%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	+	0.4565	45.65%
Acute Oral Toxicity (c)	III	0.7306	73.06%
Estrogen receptor binding	-	0.8915	89.15%
Androgen receptor binding	-	0.8572	85.72%
Thyroid receptor binding	-	0.8638	86.38%
Glucocorticoid receptor binding	-	0.8489	84.89%
Aromatase binding	-	0.8694	86.94%
PPAR gamma	-	0.8314	83.14%
Honey bee toxicity	-	0.9616	96.16%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.9700	97.00%
Fish aquatic toxicity	-	0.9191	91.91%

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	94.95%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.48%	96.09%
CHEMBL2581	P07339	Cathepsin D	86.00%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	85.35%	90.17%
CHEMBL284	P27487	Dipeptidyl peptidase IV	83.25%	95.69%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.02%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.00%	96.47%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.88%	93.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.11%	95.50%

Plants that contains it

• Croton megistocarpus
• Geranium sibiricum
• Lagerstroemia indica
• Machilus japonica
• Quararibea funebris
• Senecio isatideus
• Strobilanthes cusia
• Trigonella foenum-graecum

Cross-Links

• PubChem: 11194416
• NPASS: NPC56867
• LOTUS: LTS0132256
• wikiData: Q105198779