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Record Information
Version1.0
Created at2020-04-17 19:09:49 UTC
Updated at2022-12-13 23:36:25 UTC
CannabisDB IDCDB005105
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameOrnithine
DescriptionOrnithine, also known as (S)-ornithine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Ornithine is a drug which is 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. Ornithine is a very strong basic compound (based on its pKa). Ornithine exists in all living species, ranging from bacteria to humans. Within humans, ornithine participates in a number of enzymatic reactions. In particular, carbamoyl phosphate and ornithine can be converted into citrulline; which is mediated by the enzyme ornithine carbamoyltransferase, mitochondrial. In addition, ornithine and urea can be biosynthesized from L-arginine; which is mediated by the enzyme arginase-1. In humans, ornithine is involved in the metabolic disorder called argininemia. Outside of the human body, Ornithine has been detected, but not quantified in, several different foods, such as lemon thymes, black elderberries, tronchuda cabbages, black mulberries, and bilberries. This could make ornithine a potential biomarker for the consumption of these foods. Ornithine is a potentially toxic compound. Ornithine, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, myopathy, lactic acidosis, and sideroblastic anemia 1, and perillyl alcohol administration for cancer treatment; ornithine has also been linked to several inborn metabolic disorders including hyperdibasic aminoaciduria I and ornithine transcarbamylase deficiency. An optically active form of ornithine having L-configuration. Ornithine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
Chemical FormulaC5H12N2O2
Average Molecular Weight132.16
Monoisotopic Molecular Weight132.0899
IUPAC Name(2S)-2,5-diaminopentanoic acid
Traditional Nameornithine
CAS Registry Number25104-12-5
SMILES
NCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
InChI KeyAHLPHDHHMVZTML-BYPYZUCNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility620 mg/mLNot Available
logP-4.22SANGSTER (1994)
Predicted Properties
PropertyValueSource
logP-3.6ALOGPS
logP-3.7ChemAxon
logS0.11ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.21 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Cationic amino acid transporter 4SLC7A422q11.21O43246 details
Mitochondrial ornithine transporter 1SLC25A1513q14Q9Y619 details
Mitochondrial ornithine transporter 2SLC25A25q31Q9BXI2 details
Cationic amino acid transporter 3SLC7A3Q8WY07 details
High affinity cationic amino acid transporter 1SLC7A113q12-q14P30825 details
Low affinity cationic amino acid transporter 2SLC7A28p22-p21.3P52569 details
Y+L amino acid transporter 2SLC7A616q22.1Q92536 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Arginase-1ARG16q23P05089 details
Aminoacylase-1ACY13p21.1Q03154 details
Arginase-2, mitochondrialARG214q24.1P78540 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0936 mg/g dry wt
    • David S. Wishart,...
details
GabriolaDetected and Quantified0.0107 mg/g dry wt
    • David S. Wishart,...
details
Island HoneyDetected and Quantified0.0351 mg/g dry wt
    • David S. Wishart,...
details
QuadraDetected and Quantified0.0155 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified0.00585 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified0.0374 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0000214
DrugBank IDDB00129
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030969
KNApSAcK IDC00001384
Chemspider ID6026
KEGG Compound IDC00077
BioCyc IDL-ORNITHINE
BiGG ID37976
Wikipedia LinkOrnithine
METLIN ID27
PubChem Compound6262
PDB IDNot Available
ChEBI ID15729
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 27 proteins in total.

Enzymes

General function:
Involved in arginase activity
Specific function:
Not Available
Gene Name:
ARG1
Uniprot ID:
P05089
Molecular weight:
34734.655
General function:
Involved in transaminase activity
Specific function:
Not Available
Gene Name:
OAT
Uniprot ID:
P04181
Molecular weight:
48534.39
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development. May be involved in the response to heart failure by elevating local creatine synthesis.
Gene Name:
GATM
Uniprot ID:
P50440
Molecular weight:
48455.01
General function:
Involved in metallopeptidase activity
Specific function:
Involved in the hydrolysis of N-acylated or N-acetylated amino acids (except L-aspartate).
Gene Name:
ACY1
Uniprot ID:
Q03154
Molecular weight:
45884.705
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme that converts glutamate to glutamate 5-semialdehyde, an intermediate in the biosynthesis of proline, ornithine and arginine.
Gene Name:
ALDH18A1
Uniprot ID:
P54886
Molecular weight:
87088.29
General function:
Involved in carboxyl- or carbamoyltransferase activity
Specific function:
Not Available
Gene Name:
OTC
Uniprot ID:
P00480
Molecular weight:
39934.775
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ODC1
Uniprot ID:
P11926
Molecular weight:
51147.73
General function:
Involved in arginase activity
Specific function:
May play a role in the regulation of extra-urea cycle arginine metabolism and also in down-regulation of nitric oxide synthesis. Extrahepatic arginase functions to regulate L-arginine bioavailability to NO synthase. Since NO synthase is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase II plays a role in both male and female sexual arousal. It is therefore a potential target for the treatment of male and female sexual arousal disorders.
Gene Name:
ARG2
Uniprot ID:
P78540
Molecular weight:
38577.515
General function:
Involved in transport
Specific function:
Involved in the transport of the cationic amino acids (arginine, lysine and ornithine)
Gene Name:
SLC7A4
Uniprot ID:
O43246
Molecular weight:
68267.2
General function:
Involved in transporter activity
Specific function:
Ornithine transport across inner mitochondrial membrane, from the cytoplasm to the matrix.
Gene Name:
SLC25A15
Uniprot ID:
Q9Y619
Molecular weight:
32735.96

Transporters

General function:
Involved in transport
Specific function:
Involved in the transport of the cationic amino acids (arginine, lysine and ornithine)
Gene Name:
SLC7A4
Uniprot ID:
O43246
Molecular weight:
68267.2
General function:
Involved in transporter activity
Specific function:
Ornithine transport across inner mitochondrial membrane, from the cytoplasm to the matrix.
Gene Name:
SLC25A15
Uniprot ID:
Q9Y619
Molecular weight:
32735.96
General function:
Involved in transporter activity
Specific function:
Ornithine transport across inner mitochondrial membrane, from the cytoplasm to the matrix.
Gene Name:
SLC25A2
Uniprot ID:
Q9BXI2
Molecular weight:
32580.07
General function:
Involved in transport
Specific function:
Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner
Gene Name:
SLC7A3
Uniprot ID:
Q8WY07
Molecular weight:
67168.3
General function:
Involved in transport
Specific function:
High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor
Gene Name:
SLC7A1
Uniprot ID:
P30825
Molecular weight:
67637.6
General function:
Involved in transport
Specific function:
Low-affinity, high capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine). Plays a regulatory role in classical or alternative activation of macrophages
Gene Name:
SLC7A2
Uniprot ID:
P52569
Molecular weight:
71672.2
General function:
Involved in transport
Specific function:
Involved in the sodium-independent uptake of dibasic amino acids and sodium-dependent uptake of some neutral amino acids. Requires co-expression with SLC3A2/4F2hc to mediate the uptake of arginine, leucine and glutamine. Also acts as an arginine/glutamine exchanger, following an antiport mechanism for amino acid transport, influencing arginine release in exchange for extracellular amino acids. Plays a role in nitric oxide synthesis in human umbilical vein endothelial cells (HUVECs) via transport of L-arginine. Involved in the transport of L-arginine in monocytes. Reduces uptake of ornithine in retinal pigment epithelial (RPE) cells
Gene Name:
SLC7A6
Uniprot ID:
Q92536
Molecular weight:
56826.9

Only showing the first 10 proteins. There are 27 proteins in total.