L-2-Amino-4-(Guanidinooxy)Butyric Acid

Identification

Name
L-2-Amino-4-(Guanidinooxy)Butyric Acid
Accession Number
DB01833  (EXPT01587)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
3HZV514J4B
CAS number
Not Available
Weight
Average: 176.1738
Monoisotopic: 176.09094027
Chemical Formula
C5H12N4O3
InChI Key
FSBIGDSBMBYOPN-VKHMYHEASA-N
InChI
InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1
IUPAC Name
(2S)-2-amino-4-(carbamimidamidooxy)butanoic acid
SMILES
N[C@@H](CCONC(N)=N)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, endothelialNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0002706
KEGG Compound
C00308
PubChem Compound
439202
PubChem Substance
46507101
ChemSpider
388342
BindingDB
50370459
ChEBI
609827
ChEMBL
CHEMBL443732
HET
GGB
PDB Entries
3lap / 3u88 / 4m2f / 4q2x / 4y4g / 5n3k / 5uti / 6nse

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.77 mg/mLALOGPS
logP-3.9ALOGPS
logP-3.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.1ChemAxon
pKa (Strongest Basic)10.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area134.45 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity61.24 m3·mol-1ChemAxon
Polarizability17.02 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6949
Blood Brain Barrier+0.776
Caco-2 permeable-0.6707
P-glycoprotein substrateNon-substrate0.6462
P-glycoprotein inhibitor INon-inhibitor0.9281
P-glycoprotein inhibitor IINon-inhibitor0.9795
Renal organic cation transporterNon-inhibitor0.8358
CYP450 2C9 substrateNon-substrate0.8185
CYP450 2D6 substrateNon-substrate0.7847
CYP450 3A4 substrateNon-substrate0.7424
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.909
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9033
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9785
Ames testAMES toxic0.7585
CarcinogenicityNon-carcinogens0.9017
BiodegradationReady biodegradable0.7581
Rat acute toxicity2.1576 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.947
hERG inhibition (predictor II)Non-inhibitor0.9137
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0uk9-2930000000-f0b7791e84a9692c9896
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0uk9-2930000000-f0b7791e84a9692c9896
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-004i-0900000000-1bb8236fdf1b58516604
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-01b9-4900000000-bb3b6e4a69d652b8ca9f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-06di-9400000000-d5093b67a7ae4861da94
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4i-9100000000-c152969360d44d895d0f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0k96-9000000000-277b39712e9095e29987
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-004i-0900000000-ba76dc7ddbe1f642142a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-004i-7900000000-e4399ab6ff268986734e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00b9-9100000000-fa6508b89d97cec98552
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-05di-9000000000-3dadb3257235bbed4b41
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0ab9-9000000000-c1e347b18ad0b5e0667e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0900000000-1bb8236fdf1b58516604
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-01b9-4900000000-6273e4c764e53645e523
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-06di-9400000000-d5093b67a7ae4861da94
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9100000000-c152969360d44d895d0f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0k96-9000000000-277b39712e9095e29987
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-0900000000-ba76dc7ddbe1f642142a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-004i-7900000000-e4399ab6ff268986734e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00b9-9100000000-e6d11248bff03dbe3f4e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05di-9000000000-444161e8e39f43477d96
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ab9-9000000000-c1e347b18ad0b5e0667e
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Fatty acids and conjugates / Guanidines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
L-alpha-amino acid / Fatty acid / Guanidine / Amino acid / Monocarboxylic acid or derivatives / Carboxylic acid / Amine / Hydrocarbon derivative / Organic oxygen compound / Organic nitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid (CHEBI:609827)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
Molecular Weight
133287.62 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 06:54