L-homoarginine

Identification

Generic Name
L-homoarginine
DrugBank Accession Number
DB03974
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 188.2275
Monoisotopic: 188.127325776
Chemical Formula
C7H16N4O2
Synonyms
  • Homo-L-arginine
  • Homoarginine
  • N6-(Aminoiminomethyl)-L-lysine
  • N6-amidino-L-Lysine
  • N6-amidino-Lysine
External IDs
  • NSC 27429
  • NSC 88868

Pharmacology

Indication

Not Available

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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Carbonyl group / Carboximidamide / Carboxylic acid / Fatty acid / Fatty acyl / Guanidine
show 13 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-lysine derivative, homoarginine (CHEBI:27747)
Affected organisms
Not Available

Chemical Identifiers

UNII
JF751CK38I
CAS number
156-86-5
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

References

General References
Not Available
Human Metabolome Database
HMDB0000670
KEGG Compound
C01924
PubChem Compound
9085
PubChem Substance
46506308
ChemSpider
8732
BindingDB
50309588
ChEBI
27747
ChEMBL
CHEMBL589752
ZINC
ZINC000001529320
PDBe Ligand
HRG
PDB Entries
1dm7 / 2vdn / 3diq / 4m2e / 5ijr / 5vbl / 5vlk / 5vlp / 5wxf / 5wxo
show 12 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-00dl-9200000000-4b838fa08e1357002dbf
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0019-1900000000-a0bd99b370cbc5693d92
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-89db0e55d28695530dfd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-9400000000-5e55b3170bbcb8c6f447
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-2900000000-54b26891c52491c33529
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-fb3b2f3e7035583d844b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-9000000000-1dab69230a72471187b2
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-152.2251149
predicted
DarkChem Lite v0.1.0
[M-H]-152.3503149
predicted
DarkChem Lite v0.1.0
[M-H]-137.66222
predicted
DeepCCS 1.0 (2019)
[M+H]+152.5343149
predicted
DarkChem Lite v0.1.0
[M+H]+152.7294149
predicted
DarkChem Lite v0.1.0
[M+H]+141.01003
predicted
DeepCCS 1.0 (2019)
[M+Na]+152.4737149
predicted
DarkChem Lite v0.1.0
[M+Na]+152.4139149
predicted
DarkChem Lite v0.1.0
[M+Na]+150.47005
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52