Input interpretation
![L-arginine](../image_source/601dff753ce2652e0071ca6ddbcd594d.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/eae5b4229c274564892cb2fb01b5e857.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/c2121d8dbb9872f289ffab0952625544.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/62938f39cf42481fd8806e66e39c5018.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/7c0ea93cc129a0de847cd35c4f1bb4fe.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/d7543cdbbc5cf95551e6b3c7be5c62d2.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/6e13e6aade9cbef3bc09ba87f4f9f3cd.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/47c5433feeb425a7fdfd307f128a7914.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/1580b8900426e2c0a163576860a3f41c.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/21baf434e50f5efc3d6ddaaa4fc54911.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/aad95e04640d4e7133033161dd0719e5.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/0bfa8a9b7a87677d4cae40de93924254.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/39431cba77a0b124d0ab18ca672cc32a.png)
NFPA label
![NFPA health rating | 1 NFPA fire rating | 0 NFPA reactivity rating | 0](../image_source/67bd5838b1e87a6b424da3237019f2ac.png)
NFPA health rating | 1 NFPA fire rating | 0 NFPA reactivity rating | 0
Safety properties
![flash point | 176 °C](../image_source/b5ad6f889f9d7850e5f323ed68637ee7.png)
flash point | 176 °C
Toxicity properties
![RTECS classes | mutagen](../image_source/f6557897449998d316fcc9dc98f2910c.png)
RTECS classes | mutagen