DL-Citrulline

Details

• Internal ID: 25d53ad8-b9e8-4950-a51a-c08292ab35ec
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids
• IUPAC Name: 2-amino-5-(carbamoylamino)pentanoic acid
• SMILES (Canonical): C(CC(C(=O)O)N)CNC(=O)N
• SMILES (Isomeric): C(CC(C(=O)O)N)CNC(=O)N
• InChI: InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)
• InChI Key: RHGKLRLOHDJJDR-UHFFFAOYSA-N
• Popularity: 1,073 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₃N₃O₃
• Molecular Weight: 175.19 g/mol
• Exact Mass: 175.09569129 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: -4.30
• Atomic LogP (AlogP): -1.15
• H-Bond Acceptor: 3
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 627-77-0
• 2-Amino-5-ureidopentanoic acid
• Citrullin
• 2-amino-5-(carbamoylamino)pentanoic acid
• DL-2-Amino-5-ureidovaleric acid
• citrulina
• CITRULLINE, (DL)
• CHEBI:18211
• Ornithine, N5-carbamoyl-, DL-
• DL-Ornithine, N5-(aminocarbonyl)-
• H-D-Orn(carbamoyl)-OH
• Citrulline, (+/-)-
• 1OYO2NV4NM
• DL-Ornithine, N(5)-(aminocarbonyl)-
• N(5)-carbamoyl-DL-ornithine
• N(5)-(aminocarbonyl)ornithine
• NSC27425
• NSC46711
• N(5)-(aminocarbonyl)-DL-ornithine
• NSC-46711
• L-citrullin
• C6H13N3O3
• N(5)-carbamoylornithine
• N~5~-carbamoyl-L-ornithine
• 2-Amino-5-uredovaleric acid
• H-Orn(carbamoyl)-OH;L-Citrulline
• MFCD00216469
• Citrulline,(l)
• EINECS 211-012-2
• citrulline (DL-form)
• Spectrum_000037
• .delta.-Ureidonorvaline
• CITRULLINE, DL-
• SpecPlus_000523
• L(+)CITRULLINE
• Spectrum2_001371
• Spectrum3_001045
• Spectrum4_001185
• Spectrum5_001792
• UNII-1OYO2NV4NM
• N.delta.-Carbamylornithine
• bmse000209
• Epitope ID:141797
• SCHEMBL20587
• BSPBio_002570
• KBioGR_001849
• KBioSS_000397
• N(.delta.)-Carbamylornithine
• DivK1c_006619
• SPBio_001322
• CHEMBL187855
• SGCUT00061
• DL-2-amino-5-ureidovalericacid
• SCHEMBL13282334
• KBio1_001563
• KBio2_000397
• KBio2_002965
• KBio2_005533
• KBio3_001790
• DTXSID40861910
• RHGKLRLOHDJJDR-UHFFFAOYSA-N
• to_000034
• CCG-38847
• MFCD00007955
• NSC 46711
• NSC206276
• s5124
• AKOS005622468
• L-(+)-2-Amino-5-ureidovaleric acid
• L-CITRULLINE (1.12117)
• CS-W017450
• HY-W016734
• PB48354
• SDCCGMLS-0066976.P001
• NCGC00178596-01
• .alpha.-Amino-.delta.-ureidovaleric acid
• AS-60168
• SY023288
• SY032853
• FT-0625451
• FT-0627745
• FT-0659369
• NORVALINE, 5-((AMINOCARBONYL)AMINO)-
• C-6150
• D89239
• EN300-1168657
• A833990
• L000975
• SR-05000002410
• 1,2,2,6,6-PENTAMETHYLPIPERIDINED-TARTRATE
• SR-05000002410-1
• Q27102910

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8283	82.83%
Caco-2	-	0.9364	93.64%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6272	62.72%
OATP2B1 inhibitior	-	0.8460	84.60%
OATP1B1 inhibitior	+	0.9718	97.18%
OATP1B3 inhibitior	+	0.9538	95.38%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9708	97.08%
P-glycoprotein inhibitior	-	0.9881	98.81%
P-glycoprotein substrate	-	0.7987	79.87%
CYP3A4 substrate	-	0.7167	71.67%
CYP2C9 substrate	+	0.7874	78.74%
CYP2D6 substrate	-	0.7842	78.42%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9149	91.49%
CYP2C19 inhibition	-	0.9018	90.18%
CYP2D6 inhibition	-	0.9700	97.00%
CYP1A2 inhibition	-	0.9415	94.15%
CYP2C8 inhibition	-	0.9897	98.97%
CYP inhibitory promiscuity	-	0.9896	98.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.7143	71.43%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9686	96.86%
Skin irritation	-	0.8302	83.02%
Skin corrosion	-	0.9085	90.85%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7117	71.17%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.9208	92.08%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8102	81.02%
Acute Oral Toxicity (c)	IV	0.5275	52.75%
Estrogen receptor binding	-	0.9131	91.31%
Androgen receptor binding	-	0.7813	78.13%
Thyroid receptor binding	-	0.8292	82.92%
Glucocorticoid receptor binding	-	0.8897	88.97%
Aromatase binding	-	0.9141	91.41%
PPAR gamma	-	0.7813	78.13%
Honey bee toxicity	-	0.9713	97.13%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.9000	90.00%
Fish aquatic toxicity	-	0.9243	92.43%

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	98.09%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.88%	99.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	90.15%	92.29%
CHEMBL233	P35372	Mu opioid receptor	89.55%	97.93%
CHEMBL2581	P07339	Cathepsin D	88.77%	98.95%
CHEMBL2514	O95665	Neurotensin receptor 2	88.68%	100.00%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	88.63%	93.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.58%	91.11%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	88.39%	97.29%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.74%	97.21%
CHEMBL221	P23219	Cyclooxygenase-1	85.56%	90.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.94%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.38%	96.95%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.21%	85.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.76%	95.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.72%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	83.54%	90.20%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.21%	94.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.08%	96.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.93%	94.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.65%	93.56%
CHEMBL2185	Q96GD4	Serine/threonine-protein kinase Aurora-B	80.64%	96.80%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	80.44%	94.01%

Plants that contains it

• Cycas revoluta

Cross-Links

• PubChem: 833
• LOTUS: LTS0031418
• wikiData: Q27102910