(2S)-2,5-diaminopentanoic acid

• ChemBase ID: 15
• Molecular Formular: C5H12N2O2
• Molecular Mass: 132.16098
• Monoisotopic Mass: 132.08987763
• SMILES: OC(=O)[C@@H](N)CCCN
• Canonical SMILES: N[C@H](C(=O)O)CCCN
• InChI: InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
• InChIKey: AHLPHDHHMVZTML-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2,5-diaminopentanoic acid
• IUPAC Traditional name: L-ornithine; ornithine
• Brand Name: OKG (Nature's Bounty)
• Synonyms: 2,5-Diaminopentanoate; 2,5-Diaminopentanoic acid; 2,5-Diaminovaleric acid; Ornithine; L-Ornithine; (+)-(S)-2,5-Diaminovaleric acid; (+)-(S)-2,5-Diaminopentanoic acid; Ornithine; (2S)-2,5-diaminopentanoic acid; (S)-2,6-Diaminohexanoic acid monohydrate; H-Lys-OH.H2O; L-Lysine monohydrate; L-赖氨酸单水合物

Database IDs

• CAS Number: 39665-12-8; 70-26-8
• EC Number: 200-294-2; 200-731-7
• MDL Number: MFCD00242584; MFCD00151035
• Beilstein Number: 1722531
• Merck Index: 145636
• PubChem SID: 160963478; 46505239
• PubChem CID: 6262
• CHEBI ID: 15729
• CHEMBL: 446143
• Chemspider ID: 6026
• DrugBank ID: DB00129
• KEGG ID: D08302
• MeSH Name: Ornithine
• Unique Ingredient Identifier: E524N2IXA3
• Wikipedia Title: Ornithine

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.6664226
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -6.399376
• LogD (pH = 7.4): -5.4160175
• Log P: -3.6582875
• Molar Refractivity: 33.2085 cm^3
• Polarizability: 13.533871 Å^3
• Polar Surface Area: 89.34 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.64
• LOG S: 0.11
• Solubility (Water): 1.72e+02 g/l

PROPERTIES

Physical Property

• Solubility: Appreciable; soluble in water
• Melting Point: 140 °C; 210°C dec.
• Optical Rotation: +11.5 (H₂O, c = 6.5); +22.5 (c=2 in 6M HCl)
• Hydrophobicity(logP): -3.3; -3.953

Safety Information

• RTECS: OL5540000
• TSCA Listed: 是

Product Information

• Purity: 95%; 98+%

DETAILS

DrugBank - DB00129

• Drug Groups: approved; nutraceutical
• Description: Ornithine is an amino acid produced in the urea cycle by the splitting off of urea from arginine. It is a central part of the urea cycle, which allows for the disposal of excess nitrogen. L-Ornithine is a precursor of citrulline and arginine.
• Indication: Used for nutritional supplementation, also for treating dietary shortage or imbalance. It has been claimed that ornithine improves athletic performance, has anabolic effects, has wound-healing effects, and is immuno-enhancing.
• Pharmacology: A non-essential and nonprotein amino acid, ornithine is critical for the production of the body's proteins, enzymes and muscle tissue. Ornithine plays a central role in the urea cycle and is important for the disposal of excess nitrogen (ammonia). Ornithine is the starting point for the synthesis of many polyamines such as putrescine and spermine. Ornithine supplements are claimed to enhance the release of growth hormone and to burn excess body fat. Ornithine is necessary for proper immune function and good liver function.
• Toxicity: Oral, rat LD₅₀ = 10000 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Ornithine undergoes extensive metabolism in the liver to L-arginine, polyamines, and proline, and several other metabolites.
• Absorption: Absorbed from the small intestine via a sodium-dependent active transport process
• External Links: Wikipedia; PDRhealth