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Identification
NameN-{(4s)-4-Amino-5-[(2-Aminoethyl)Amino]Pentyl}-N'-Nitroguanidine
Accession NumberDB02027  (EXPT01253)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 247.298
Monoisotopic: 247.175672951
Chemical FormulaC8H21N7O2
InChI KeyRMSWBHUVFNFNIZ-ZETCQYMHSA-N
InChI
InChI=1S/C8H21N7O2/c9-3-5-12-6-7(10)2-1-4-13-8(11)14-15(16)17/h7,12H,1-6,9-10H2,(H3,11,13,14)/t7-/m0/s1
IUPAC Name
3-[(4S)-4-amino-5-[(2-aminoethyl)amino]pentyl]-1-nitroguanidine
SMILES
NCCNC[C@@H](N)CCCNC(=N)N[N+]([O-])=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Nitric oxide synthase, endothelialProteinunknownNot AvailableHumanP29474 details
Nitric oxide synthase, brainProteinunknownNot AvailableHumanP29475 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7614
Blood Brain Barrier+0.7658
Caco-2 permeable-0.5863
P-glycoprotein substrateSubstrate0.5366
P-glycoprotein inhibitor INon-inhibitor0.9295
P-glycoprotein inhibitor IINon-inhibitor0.9405
Renal organic cation transporterNon-inhibitor0.7153
CYP450 2C9 substrateNon-substrate0.8917
CYP450 2D6 substrateNon-substrate0.7677
CYP450 3A4 substrateNon-substrate0.7287
CYP450 1A2 substrateNon-inhibitor0.838
CYP450 2C9 inhibitorNon-inhibitor0.8482
CYP450 2D6 inhibitorNon-inhibitor0.9005
CYP450 2C19 inhibitorNon-inhibitor0.8375
CYP450 3A4 inhibitorNon-inhibitor0.9418
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9763
Ames testAMES toxic0.858
CarcinogenicityNon-carcinogens0.6753
BiodegradationNot ready biodegradable0.586
Rat acute toxicity2.4278 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8309
hERG inhibition (predictor II)Non-inhibitor0.8151
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.338 mg/mLALOGPS
logP-1.4ALOGPS
logP-2.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)10.3ChemAxon
pKa (Strongest Basic)9.72ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area157.8 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity75.42 m3·mol-1ChemAxon
Polarizability25.98 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as nitramines. These are organyl derivatives of nitramide with the general formula RNHO2 (R = organyl group).
KingdomOrganic compounds
Super ClassOrganic 1,3-dipolar compounds
ClassAllyl-type 1,3-dipolar organic compounds
Sub ClassOrganic nitro compounds
Direct ParentNitramines
Alternative Parents
Substituents
  • Nitramine
  • Guanidine
  • Carboximidamide
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organic salt
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Imine
  • Amine
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available

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)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by ...
Gene Name:
NOS3
Uniprot ID:
P29474
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Tetrahydrobiopterin binding
Specific Function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR.
Gene Name:
NOS1
Uniprot ID:
P29475
Molecular Weight:
160969.095 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23