L-Homocitrulline

Details

• Internal ID: dea78907-1ce8-4d67-89d8-62eb715b8f09
• 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-(carbamoylamino)hexanoic acid
• SMILES (Canonical): C(CCNC(=O)N)CC(C(=O)O)N
• SMILES (Isomeric): C(CCNC(=O)N)C[C@@H](C(=O)O)N
• InChI: InChI=1S/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1
• InChI Key: XIGSAGMEBXLVJJ-YFKPBYRVSA-N
• Popularity: 405 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₅N₃O₃
• Molecular Weight: 189.21 g/mol
• Exact Mass: 189.11134135 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -0.76
• H-Bond Acceptor: 3
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• 1190-49-4
• Homocitrulline
• (S)-2-Amino-6-ureidohexanoic acid
• Homo-L-citrulline
• (2S)-2-amino-6-(carbamoylamino)hexanoic acid
• L-Lysine, N6-(aminocarbonyl)-
• N(6)-carbamoyl-L-lysine
• DL-Homocitrulline
• N6-carbamoyl-L-Lysine
• N(6)-(aminocarbonyl)-L-lysine
• 133T7A0Y5K
• L-Lysine, N(6)-(aminocarbonyl)-
• (2S)-2-azaniumyl-6-(carbamoylamino)hexanoate
• Homocitrulline, L-
• H-HOMOCIT-OH
• (S)-2-Amino-6-ureidocaproic acid
• UNII-133T7A0Y5K
• MFCD00038143
• NSC-27428
• EINECS 214-722-0
• n6-carbamoyl-lysine
• NSC 27428
• N-e-Carbamyl-L-lysine
• N~6~-carbamoyl-L-lysine
• bmse000442
• N-epsilon-Carbamyl-L-lysine
• SCHEMBL56915
• LYSINE, N6-CARBAMOYL-
• CHEBI:17443
• XIGSAGMEBXLVJJ-YFKPBYRVSA-
• DTXSID301317386
• AMY22717
• LYSINE, N6-CARBAMOYL-, L-
• s6128
• AKOS006272047
• N-.EPSILON.-CARBAMYL-L-LYSINE
• 2-amino-6-carbamoylamino-hexanoic acid
• CS-W018790
• HY-W018004
• DS-15012
• C02427
• A892674
• J-004062
• Q18207833
• InChI=1/C7H15N3O3/c8-5(6(11)12)3-1-2-4-10-7(9)13/h5H,1-4,8H2,(H,11,12)(H3,9,10,13)/t5-/m0/s1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7991	79.91%
Caco-2	-	0.8561	85.61%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6789	67.89%
OATP2B1 inhibitior	-	0.8465	84.65%
OATP1B1 inhibitior	+	0.9747	97.47%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9677	96.77%
P-glycoprotein inhibitior	-	0.9835	98.35%
P-glycoprotein substrate	-	0.7577	75.77%
CYP3A4 substrate	-	0.6890	68.90%
CYP2C9 substrate	+	0.7874	78.74%
CYP2D6 substrate	-	0.7842	78.42%
CYP3A4 inhibition	-	0.8394	83.94%
CYP2C9 inhibition	-	0.9182	91.82%
CYP2C19 inhibition	-	0.9053	90.53%
CYP2D6 inhibition	-	0.9691	96.91%
CYP1A2 inhibition	-	0.9354	93.54%
CYP2C8 inhibition	-	0.9888	98.88%
CYP inhibitory promiscuity	-	0.9869	98.69%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9794	97.94%
Skin irritation	-	0.8267	82.67%
Skin corrosion	-	0.9283	92.83%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6264	62.64%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9207	92.07%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.6970	69.70%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8165	81.65%
Acute Oral Toxicity (c)	III	0.4744	47.44%
Estrogen receptor binding	-	0.8735	87.35%
Androgen receptor binding	-	0.7464	74.64%
Thyroid receptor binding	-	0.7924	79.24%
Glucocorticoid receptor binding	-	0.7634	76.34%
Aromatase binding	-	0.8765	87.65%
PPAR gamma	-	0.7206	72.06%
Honey bee toxicity	-	0.9721	97.21%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	-	0.8258	82.58%

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	99.11%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.05%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.07%	99.17%
CHEMBL2581	P07339	Cathepsin D	89.82%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.39%	91.11%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	89.07%	92.29%
CHEMBL233	P35372	Mu opioid receptor	88.44%	97.93%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	88.37%	97.29%
CHEMBL2514	O95665	Neurotensin receptor 2	88.31%	100.00%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	88.04%	93.56%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.70%	97.21%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.21%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.88%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	85.70%	90.20%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.35%	96.95%
CHEMBL221	P23219	Cyclooxygenase-1	82.97%	90.17%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.81%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.93%	94.33%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	80.69%	94.01%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.16%	93.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 65072
• LOTUS: LTS0110114
• wikiData: Q18207833