Input interpretation
![L-arginine](../image_source/5d1a29719cb6fd8d9419768c78d42834.png)
L-arginine
Chemical names and formulas
![formula | H_2NC(=NH)NH(CH_2)_3CH(NH_2)CO_2H Hill formula | C_6H_14N_4O_2 name | L-arginine IUPAC name | (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid alternate names | (S)-2-amino-5-guanidinopentanoic acid mass fractions | C (carbon) 41.4% | H (hydrogen) 8.1% | N (nitrogen) 32.2% | O (oxygen) 18.4%](../image_source/f56b806ca5a50ad63916175455a54e0a.png)
formula | H_2NC(=NH)NH(CH_2)_3CH(NH_2)CO_2H Hill formula | C_6H_14N_4O_2 name | L-arginine IUPAC name | (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid alternate names | (S)-2-amino-5-guanidinopentanoic acid mass fractions | C (carbon) 41.4% | H (hydrogen) 8.1% | N (nitrogen) 32.2% | O (oxygen) 18.4%
Lewis structure
![Draw the Lewis structure of L-arginine. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), and oxygen (n_O, val = 6) atoms: 6 n_C, val + 14 n_H, val + 4 n_N, val + 2 n_O, val = 70 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), and oxygen (n_O, full = 8): 6 n_C, full + 14 n_H, full + 4 n_N, full + 2 n_O, full = 124 Subtracting these two numbers shows that 124 - 70 = 54 bonding electrons are needed. Each bond has two electrons, so in addition to the 25 bonds already present in the diagram add 2 bonds. To minimize formal charge carbon wants 4 bonds, nitrogen wants 3 bonds, and oxygen wants 2 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 2 bonds by pairing electrons between adjacent highlighted atoms: Answer: | |](../image_source/304ff3d0f8a56c054932fd1e0b8aad6d.png)
Draw the Lewis structure of L-arginine. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the carbon (n_C, val = 4), hydrogen (n_H, val = 1), nitrogen (n_N, val = 5), and oxygen (n_O, val = 6) atoms: 6 n_C, val + 14 n_H, val + 4 n_N, val + 2 n_O, val = 70 Calculate the number of electrons needed to completely fill the valence shells for carbon (n_C, full = 8), hydrogen (n_H, full = 2), nitrogen (n_N, full = 8), and oxygen (n_O, full = 8): 6 n_C, full + 14 n_H, full + 4 n_N, full + 2 n_O, full = 124 Subtracting these two numbers shows that 124 - 70 = 54 bonding electrons are needed. Each bond has two electrons, so in addition to the 25 bonds already present in the diagram add 2 bonds. To minimize formal charge carbon wants 4 bonds, nitrogen wants 3 bonds, and oxygen wants 2 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 2 bonds by pairing electrons between adjacent highlighted atoms: Answer: | |
3D structure
![3D structure](../image_source/9dd59432868cf60a335cf70b859b7dab.png)
3D structure
Basic properties
![molar mass | 174.2 g/mol phase | solid (at STP) melting point | 222 °C boiling point | 368 °C density | 1.3 g/cm^3](../image_source/a6063d5286407645cd80ddcc26c91c84.png)
molar mass | 174.2 g/mol phase | solid (at STP) melting point | 222 °C boiling point | 368 °C density | 1.3 g/cm^3
Units
Hydrophobicity and permeability properties
![experimental LogP hydrophobicity | -3.6 predicted LogP hydrophobicity | -3.86 predicted LogS | -1.36](../image_source/8659f7f1daed83114be2e4cb6c6da38b.png)
experimental LogP hydrophobicity | -3.6 predicted LogP hydrophobicity | -3.86 predicted LogS | -1.36
Basic drug properties
![approval status | approved | nutraceutical | small molecule drug categories | conditionally essential amino acid | dietary supplement | micronutrient dosage forms | intravenous: liquid](../image_source/dc8aa6cedbaab3bccd3b871b5648d2b1.png)
approval status | approved | nutraceutical | small molecule drug categories | conditionally essential amino acid | dietary supplement | micronutrient dosage forms | intravenous: liquid
![brand names | argamine | argivene | detoxargin | levargin | minophagen A | R-gene 10 (pharmacia corp.)](../image_source/507870b392a37057d9c1a03eab84837f.png)
brand names | argamine | argivene | detoxargin | levargin | minophagen A | R-gene 10 (pharmacia corp.)
Amino acid properties
![three-letter code | Arg one-letter code | R isoelectric point | 10.76 pK_a (α-COOH, (α-NH_3)^+) | 1.82 | 8.99 pK_a of side-chain | 12.48 polarity | basic polar codons | CGU | CGC | CGA | CGG | AGA | AGG occurrence in human proteins | 5.86%](../image_source/2bea05cbe181912030c29b4084e81983.png)
three-letter code | Arg one-letter code | R isoelectric point | 10.76 pK_a (α-COOH, (α-NH_3)^+) | 1.82 | 8.99 pK_a of side-chain | 12.48 polarity | basic polar codons | CGU | CGC | CGA | CGG | AGA | AGG occurrence in human proteins | 5.86%
Solid properties (at STP)
![density | 1.3 g/cm^3 vapor pressure | 2.1×10^-6 mmHg (at 25 °C)](../image_source/b07619b0c647623479366e9c19e07a51.png)
density | 1.3 g/cm^3 vapor pressure | 2.1×10^-6 mmHg (at 25 °C)
Units
Thermodynamic properties
![molar heat of vaporization | 67.5 kJ/mol specific heat of vaporization | 0.387 kJ/g molar heat of combustion | 3737 kJ/mol specific heat of combustion | 21.45 kJ/g (at STP)](../image_source/603d99b574cdd38287d3a8c3053ef89f.png)
molar heat of vaporization | 67.5 kJ/mol specific heat of vaporization | 0.387 kJ/g molar heat of combustion | 3737 kJ/mol specific heat of combustion | 21.45 kJ/g (at STP)
Chemical identifiers
![CAS number | 74-79-3 Beilstein number | 1725413 PubChem CID number | 6322 PubChem SID number | 17397138 SMILES identifier | NC(CCCN=C(N)N)C(O)=O InChI identifier | InChI=1/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H, 1-3, 7H2, (H, 11, 12)(H4, 8, 9, 10)/t4-/m0/s1/f/h11H, 8-9H2 InChI key | ODKSFYDXXFIFQN-SMLZDNMQDI RTECS number | CF1934200 MDL number | MFCD00002635](../image_source/5ec1466672dc7c7e375224c93bb06ee0.png)
CAS number | 74-79-3 Beilstein number | 1725413 PubChem CID number | 6322 PubChem SID number | 17397138 SMILES identifier | NC(CCCN=C(N)N)C(O)=O InChI identifier | InChI=1/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H, 1-3, 7H2, (H, 11, 12)(H4, 8, 9, 10)/t4-/m0/s1/f/h11H, 8-9H2 InChI key | ODKSFYDXXFIFQN-SMLZDNMQDI RTECS number | CF1934200 MDL number | MFCD00002635
NFPA label
![NFPA label](../image_source/255fc4ec46aa68549871d8fb4ebcc06f.png)
NFPA label
![NFPA health rating | 1 NFPA fire rating | 0 NFPA reactivity rating | 0](../image_source/4e2561c7d501f5ad0fc1a5e7a5d0cfee.png)
NFPA health rating | 1 NFPA fire rating | 0 NFPA reactivity rating | 0
Safety properties
![flash point | 176 °C](../image_source/9132b2068c9a7f3c75f38cb2b6785c0e.png)
flash point | 176 °C
Toxicity properties
![RTECS classes | mutagen](../image_source/1e2d396ec12335a6c0a04c734f9d52b3.png)
RTECS classes | mutagen