L-Homoarginine

Details

• Internal ID: f3995d9b-3270-4c1d-a393-312157746422
• 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-amino-6-(diaminomethylideneamino)hexanoic acid
• SMILES (Canonical): C(CCN=C(N)N)CC(C(=O)O)N
• SMILES (Isomeric): C(CCN=C(N)N)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1
• InChI Key: QUOGESRFPZDMMT-YFKPBYRVSA-N
• Popularity: 1,097 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₆N₄O₂
• Molecular Weight: 188.23 g/mol
• Exact Mass: 188.12732577 g/mol
• Topological Polar Surface Area (TPSA): 128.00 Ų
• XlogP: -3.70
• Atomic LogP (AlogP): -1.16
• H-Bond Acceptor: 3
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• homoarginine
• 156-86-5
• H-HoArg-OH
• homo-l-arginine
• n6-amidino-lysine
• (S)-2-Amino-6-guanidinohexanoic acid
• L-N(sup 6)-Amidinolysine
• L-Lysine, N6-(aminoiminomethyl)-
• N6-amidino-L-Lysine
• N6-(Aminoiminomethyl)-L-lysine
• H-HomoArg-OH
• Homoarginine, L-
• L-Lysine, N(sup 6)-(aminoiminomethyl)-
• NSC 27429
• UNII-JF751CK38I
• LYSINE, N(sup 6)-AMIDINO-, L-
• CHEMBL589752
• JF751CK38I
• CHEBI:27747
• 13094-78-5
• N6-carbamimidoyl-L-lysine
• h-Homoarginine
• MFCD00237108
• NSC-27429
• NSC-88868
• HRG
• L-HomoArg-OH
• L-Lysine, N(6)-(aminoiminomethyl)-
• L-N(6)-amidinolysine
• N~6~-Carbamimidoyllysine
• bmse000745
• D0F8VS
• SCHEMBL43287
• LYSINE, N6-AMIDINO-
• (2S)-2-amino-6-(diaminomethylideneamino)hexanoic acid
• SCHEMBL21802133
• DTXSID70926980
• LYSINE, N6-AMIDINO-, L-
• AMY22584
• AC2507
• BDBM50309588
• s6109
• AKOS006282043
• AKOS015894481
• CS-W008385
• DB03974
• HY-W008385
• DS-15039
• LS-88422
• L-Lysine, N6-(aminoiminomethyl)- (9CI)
• (2S)-2-amino-6-carbamimidamidohexanoic acid
• C01924
• A809778
• Q-201303
• (S)-2-Amino-6-guanidinohexanoic acid (H-L-hArg-OH)
• Q57828472

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9048	90.48%
Caco-2	-	0.8055	80.55%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6641	66.41%
OATP2B1 inhibitior	-	0.8480	84.80%
OATP1B1 inhibitior	+	0.9535	95.35%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9603	96.03%
P-glycoprotein inhibitior	-	0.9841	98.41%
P-glycoprotein substrate	-	0.9270	92.70%
CYP3A4 substrate	-	0.6921	69.21%
CYP2C9 substrate	-	0.5960	59.60%
CYP2D6 substrate	-	0.7636	76.36%
CYP3A4 inhibition	-	0.8968	89.68%
CYP2C9 inhibition	-	0.9266	92.66%
CYP2C19 inhibition	-	0.9014	90.14%
CYP2D6 inhibition	-	0.9355	93.55%
CYP1A2 inhibition	-	0.7414	74.14%
CYP2C8 inhibition	-	0.9795	97.95%
CYP inhibitory promiscuity	-	0.9942	99.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.6062	60.62%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8718	87.18%
Skin irritation	-	0.7424	74.24%
Skin corrosion	-	0.8168	81.68%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7084	70.84%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8514	85.14%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	-	0.6414	64.14%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.5846	58.46%
Acute Oral Toxicity (c)	IV	0.5561	55.61%
Estrogen receptor binding	-	0.8029	80.29%
Androgen receptor binding	-	0.8187	81.87%
Thyroid receptor binding	-	0.7611	76.11%
Glucocorticoid receptor binding	-	0.6974	69.74%
Aromatase binding	-	0.6901	69.01%
PPAR gamma	-	0.7325	73.25%
Honey bee toxicity	-	0.9593	95.93%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.9000	90.00%
Fish aquatic toxicity	-	0.8686	86.86%

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	97.76%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.72%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.33%	99.17%
CHEMBL233	P35372	Mu opioid receptor	87.65%	97.93%
CHEMBL236	P41143	Delta opioid receptor	87.35%	99.35%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.02%	96.95%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	86.72%	93.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.56%	91.11%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	84.98%	92.29%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.52%	94.45%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.36%	97.88%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.86%	100.00%
CHEMBL2514	O95665	Neurotensin receptor 2	83.51%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.04%	97.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.02%	90.71%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.60%	97.29%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.05%	93.56%
CHEMBL1255126	O15151	Protein Mdm4	80.71%	90.20%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.02%	96.47%

Plants that contains it

• Capparis masaikai
• Kopsia singapurensis
• Lathyrus sativus
• Lathyrus tingitanus
• Nectandra pichurim
• Pityrogramma ebenea
• Teucrium bidentatum
• Teucrium pernyi

Cross-Links

• PubChem: 9085
• NPASS: NPC278881
• LOTUS: LTS0201302
• wikiData: Q104993546