L-Norleucine

Details

• Internal ID: 778bc515-7af5-4c77-b5b0-55cad5b072a0
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids > L-alpha-amino acids
• IUPAC Name: (2S)-2-aminohexanoic acid
• SMILES (Canonical): CCCCC(C(=O)O)N
• SMILES (Isomeric): CCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m0/s1
• InChI Key: LRQKBLKVPFOOQJ-YFKPBYRVSA-N
• Popularity: 3,517 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17 g/mol
• Exact Mass: 131.094628657 g/mol
• Topological Polar Surface Area (TPSA): 63.30 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): 0.59
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• NORLEUCINE
• 327-57-1
• (S)-2-Aminohexanoic acid
• H-Nle-OH
• L-(+)-Norleucine
• (2S)-2-aminohexanoic acid
• L-2-Aminohexanoate
• Glycoleucine
• Caprine
• L-2-Aminohexanoic acid
• 2-Aminocaproic acid
• Hexanoic acid, 2-amino-, (S)-
• alpha-Aminocaproic acid
• (S)-Norleucine
• (S)-(+)-2-Aminohexanoic acid
• L-Aminohexanoate
• 2S-amino-hexanoic acid
• (S)-2-Aminocaproic acid
• Norleucine, L-
• L(+)-Norleucine
• NSC 10378
• L-Aminohexanoic acid
• (S)-2-amino-Hexanoic acid
• CHEBI:18347
• 832C8OV84S
• NSC-10378
• NLE
• (S)-2-aminohexanoate
• Norleucine (VAN)
• MFCD00064423
• 2-amino-hexanoic acid
• 496-90-2
• .alpha.-Aminocaproic acid
• EINECS 206-321-4
• BRN 1721750
• UNII-832C8OV84S
• 2-Aminocaproate
• 2-Aminohexanoate
• (S)-Aminohexanoate
• (S)-Aminohexanoic acid
• NORLEUCINE [MI]
• H-Nle-OH L-Norleucine
• (S)-2-amino-Hexanoate
• (S)-2-aminohexanoicacid
• bmse000411
• SCHEMBL8393
• n-C4H9CH(NH2)COOH
• 4-04-00-02686 (Beilstein Handbook Reference)
• N6877_SIGMA
• CHEMBL292439
• (S)-()-2-Aminohexanoic acid
• DTXSID70883362
• L-Norleucine, >=98% (TLC)
• HY-Y0017
• FD3031
• LMFA01100042
• AKOS006240047
• AM82584
• CS-W020710
• DB15458
• AC-22372
• AS-13136
• N0303
• C01933
• EN300-134822
• M03242
• N-8800
• A827805
• Q415428
• J-300345
• B9CD20C9-2708-47D2-BEF1-0BA8BB0628AC
• Z1203162297
• L-Norleucine, suitable for amino acid analysis, BioReagent

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	-	0.7185	71.85%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Lysosomes	0.6787	67.87%
OATP2B1 inhibitior	-	0.8402	84.02%
OATP1B1 inhibitior	+	0.9502	95.02%
OATP1B3 inhibitior	+	0.9335	93.35%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9395	93.95%
P-glycoprotein inhibitior	-	0.9892	98.92%
P-glycoprotein substrate	-	0.9568	95.68%
CYP3A4 substrate	-	0.7602	76.02%
CYP2C9 substrate	-	0.5862	58.62%
CYP2D6 substrate	-	0.7981	79.81%
CYP3A4 inhibition	-	0.9346	93.46%
CYP2C9 inhibition	-	0.9087	90.87%
CYP2C19 inhibition	-	0.9187	91.87%
CYP2D6 inhibition	-	0.9056	90.56%
CYP1A2 inhibition	-	0.5715	57.15%
CYP2C8 inhibition	-	0.9896	98.96%
CYP inhibitory promiscuity	-	0.9660	96.60%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6700	67.00%
Carcinogenicity (trinary)	Non-required	0.6918	69.18%
Eye corrosion	-	0.9047	90.47%
Eye irritation	-	0.5060	50.60%
Skin irritation	-	0.6691	66.91%
Skin corrosion	+	0.9039	90.39%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7583	75.83%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.6552	65.52%
skin sensitisation	-	0.8615	86.15%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	-	0.5950	59.50%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6965	69.65%
Acute Oral Toxicity (c)	III	0.5612	56.12%
Estrogen receptor binding	-	0.9121	91.21%
Androgen receptor binding	-	0.7859	78.59%
Thyroid receptor binding	-	0.8746	87.46%
Glucocorticoid receptor binding	-	0.8747	87.47%
Aromatase binding	-	0.9297	92.97%
PPAR gamma	-	0.8589	85.89%
Honey bee toxicity	-	0.9975	99.75%
Biodegradation	+	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.6476	64.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.67%	96.09%
CHEMBL1907	P15144	Aminopeptidase N	94.41%	93.31%
CHEMBL2581	P07339	Cathepsin D	94.28%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.89%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.39%	96.95%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	91.05%	92.29%
CHEMBL236	P41143	Delta opioid receptor	90.77%	99.35%
CHEMBL3359	P21462	Formyl peptide receptor 1	90.40%	93.56%
CHEMBL221	P23219	Cyclooxygenase-1	90.31%	90.17%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	89.67%	97.29%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.23%	97.21%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.11%	96.47%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.08%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.75%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	80.53%	83.82%
CHEMBL2514	O95665	Neurotensin receptor 2	80.49%	100.00%

Plants that contains it

• Arabidopsis thaliana
• Astragalus hamosus
• Pogostemon cablin

Cross-Links

• PubChem: 21236
• LOTUS: LTS0132632
• wikiData: Q415428