L-Homoarginine

Identification

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Name
L-Homoarginine
Accession Number
DB03974  (EXPT01779)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC 27429 / NSC 88868
Categories
Not Available
UNII
JF751CK38I
CAS number
Not Available
Weight
Average: 188.2275
Monoisotopic: 188.127325776
Chemical Formula
C7H16N4O2
InChI Key
QUOGESRFPZDMMT-YFKPBYRVSA-N
InChI
InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1
IUPAC Name
(2S)-2-amino-6-carbamimidamidohexanoic acid
SMILES
N[C@@H](CCCCNC(N)=N)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, endothelialNot AvailableHumans
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
HMDB0000670
KEGG Compound
C01924
PubChem Compound
9085
PubChem Substance
46506308
ChemSpider
8732
BindingDB
50309588
ChEBI
27747
ChEMBL
CHEMBL589752
HET
HRG
PDB Entries
1dm7 / 2vdn / 3diq / 4m2e / 5ijr / 5vbl / 5vlk / 5vlp / 5wxf / 5wxo
show 3 more

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 Solubility1.58 mg/mLALOGPS
logP-3.7ALOGPS
logP-2.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)12.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area125.22 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity58.52 m3·mol-1ChemAxon
Polarizability20.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6941
Blood Brain Barrier+0.6076
Caco-2 permeable-0.7228
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.9889
P-glycoprotein inhibitor IINon-inhibitor0.8674
Renal organic cation transporterNon-inhibitor0.7721
CYP450 2C9 substrateNon-substrate0.787
CYP450 2D6 substrateNon-substrate0.704
CYP450 3A4 substrateNon-substrate0.8101
CYP450 1A2 substrateNon-inhibitor0.8129
CYP450 2C9 inhibitorNon-inhibitor0.9003
CYP450 2D6 inhibitorNon-inhibitor0.925
CYP450 2C19 inhibitorNon-inhibitor0.7873
CYP450 3A4 inhibitorNon-inhibitor0.9295
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9937
Ames testAMES toxic0.7175
CarcinogenicityNon-carcinogens0.9257
BiodegradationReady biodegradable0.9261
Rat acute toxicity1.7827 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.93
hERG inhibition (predictor II)Non-inhibitor0.9541
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-000i-1900000000-be624ee9b24e82eb0742
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-001i-9100000000-f4d4f5ac890116d181f0
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-053r-9000000000-4414ba2f5a6f7d2b30cc
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-0900000000-46385e830fe015de53ab
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0002-0900000000-c6d6b6435e521a93b453
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0002-0900000000-6e5c16a8db2bbd58844f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0002-6900000000-a844ac9257f1ef5a3b23
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-f496e2b96544aa9df21d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-000i-0900000000-860f0c1c052c981b2f3b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001c-1900000000-6ea950560557eb3afd98
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-001i-9300000000-d110eb7150669bcdc29c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-001i-9000000000-2f0ed2e02fdc77532125
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-001i-9000000000-d1b2d06e85c976b4efa5
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/MSsplash10-000i-0900000000-46385e830fe015de53ab
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-c6d6b6435e521a93b453
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-e278e373c633748b7f2a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-6900000000-2a53a55ea05925b3a0e7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-f496e2b96544aa9df21d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0900000000-860f0c1c052c981b2f3b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001c-1900000000-1dd352f7b9d2b7d3a725
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9300000000-f12f1e8092590e19aa5b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-a38a229535f2850ad836
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-f3a9a39d24ade83542ac
13C NMR Spectrum1D NMRNot Applicable
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
Medium-chain fatty acids / Amino fatty acids / Guanidines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 3 more
Substituents
L-alpha-amino acid / Medium-chain fatty acid / Amino fatty acid / Fatty acid / Fatty acyl / Guanidine / Amino acid / Carboximidamide / Monocarboxylic acid or derivatives / Carboxylic acid
show 13 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-lysine derivative, homoarginine (CHEBI:27747)

Targets

Kind
Protein
Organism
Humans
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 04, 2019 05:58