| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:47:23 UTC |
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| Update Date | 2020-06-04 19:39:56 UTC |
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| BMDB ID | BMDB0001539 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Dimethyl-L-arginine |
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| Description | Asymmetric dimethylarginine, also known as N(g),N(g)-dimethylarginine or guanidino-N,N-dimethylarginine, belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Asymmetric dimethylarginine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Asymmetric dimethylarginine exists in all eukaryotes, ranging from yeast to humans. Asymmetric dimethylarginine is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| ADMA | ChEBI | | Guanidino-N,N-dimethylarginine | ChEBI | | N,N-Dimethylarginine | ChEBI | | N(5)-((Dimethylamino)iminomethyl)-L-ornithine | ChEBI | | NG,NG-Dimethyl-L-arginine | ChEBI | | N(g),N(g)-Dimethylarginine | ChEBI | | N(g)-Dimethylarginine | ChEBI | | N(g1),N(g1)-Dimethylarginine | ChEBI | | Nomega,nomega-dimethyl-L-arginine | Kegg | | 2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoate | HMDB | | 2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acid | HMDB | | Dimethyl-L-arginine | HMDB | | N(Omega),N(omega)-dimethyl-L-arginine | HMDB | | NG,NG-Dimethylarginine | HMDB | | NG-Dimethylarginine | HMDB | | Nomega,nomega'-dimethyl-L-arginine | HMDB | | Asymmetric dimethylarginine | ChEBI |
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| Chemical Formula | C8H18N4O2 |
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| Average Molecular Weight | 202.2541 |
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| Monoisotopic Molecular Weight | 202.14297584 |
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| IUPAC Name | (2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid |
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| Traditional Name | asymmetric dimethylarginine |
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| CAS Registry Number | 30315-93-6 |
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| SMILES | N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O |
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| InChI Identifier | InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1 |
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| InChI Key | YDGMGEXADBMOMJ-LURJTMIESA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Arginine and derivatives |
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| Alternative Parents | |
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| Substituents | - Arginine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Fatty acid
- Guanidine
- Amino acid
- Carboximidamide
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Hydrocarbon derivative
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Imine
- Carbonyl group
- Amine
- Organic nitrogen compound
- Organic oxide
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Blood | Detected and Quantified | 1.1 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 1.3-2.1 uM | Not Specified | Not Specified | Normal | | details | | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 1 +/- 1 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 0.8 +/- 0.2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.08 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.09 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.1 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 0.10 +/- 0.01 uM | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 4 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 0.33 +/- 0.14 uM | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 0.9 +/- 0.2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 0.8 +/- 0.2 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
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