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Record Information
Version2.0
Created at2022-09-02 05:51:45 UTC
Updated at2022-09-02 05:51:45 UTC
NP-MRD IDNP0149900
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-{[3-(aminomethyl)phenyl]methyl}ethanimidamide
DescriptionN-[3-(aminomethyl)benzyl]acetamidine, also known as 1400 W or W1400, belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. N-[3-(aminomethyl)benzyl]acetamidine is a very strong basic compound (based on its pKa). n-{[3-(aminomethyl)phenyl]methyl}ethanimidamide is found in Crotalaria pallida. n-{[3-(aminomethyl)phenyl]methyl}ethanimidamide was first documented in 2001 (PMID: 11459438). An aralkylamine that is Nbenzylacetamidine substituted at position 3 on the benzene ring by an aminomethyl group (PMID: 25619924) (PMID: 26362773) (PMID: 26526764).
Structure
Thumb
Synonyms
ValueSource
1400 WChEBI
1400WChEBI
W1400ChEBI
1400W CPDMeSH
Chemical FormulaC10H15N3
Average Mass177.2462 Da
Monoisotopic Mass177.12660 Da
IUPAC NameN-{[3-(aminomethyl)phenyl]methyl}ethanimidamide
Traditional NameN-{[3-(aminomethyl)phenyl]methyl}ethanimidamide
CAS Registry NumberNot Available
SMILES
CC(=N)NCC1=CC=CC(CN)=C1
InChI Identifier
InChI=1S/C10H15N3/c1-8(12)13-7-10-4-2-3-9(5-10)6-11/h2-5H,6-7,11H2,1H3,(H2,12,13)
InChI KeyRODUKNYOEVZQPR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Crotalaria pallidaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Benzylamine
  • Phenylmethylamine
  • Aralkylamine
  • Amidine
  • Carboxylic acid amidine
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Primary amine
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.35ALOGPS
logP0.17ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)12.16ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.9 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.92 m³·mol⁻¹ChemAxon
Polarizability20.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB02044
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1433
PDB ID14W
ChEBI ID90721
Good Scents IDNot Available
References
General References
  1. Menchen LA, Colon AL, Moro MA, Leza JC, Lizasoain I, Menchen P, Alvarez E, Lorenzo P: N-(3-(aminomethyl)benzyl)acetamidine, an inducible nitric oxide synthase inhibitor, decreases colonic inflammation induced by trinitrobenzene sulphonic acid in rats. Life Sci. 2001 Jun 15;69(4):479-91. doi: 10.1016/s0024-3205(01)01139-0. [PubMed:11459438 ]
  2. Overso Hansen P, Kringelholt S, Simonsen U, Bek T: Hypoxia-induced relaxation of porcine retinal arterioles in vitro depends on inducible NO synthase and EP4 receptor stimulation in the perivascular retina. Acta Ophthalmol. 2015 Aug;93(5):457-63. doi: 10.1111/aos.12669. Epub 2015 Jan 25. [PubMed:25619924 ]
  3. Gautam M, Kumar R, Prasoon P, Ray SB: Antinociceptive effect of 1400 W, an inhibitor of inducible nitric oxide synthase, following hind paw incision in rats. Nitric Oxide. 2015 Nov 15;50:98-104. doi: 10.1016/j.niox.2015.09.003. Epub 2015 Sep 8. [PubMed:26362773 ]
  4. Guo C, Atochina-Vasserman E, Abramova H, George B, Manoj V, Scott P, Gow A: Role of NOS2 in pulmonary injury and repair in response to bleomycin. Free Radic Biol Med. 2016 Feb;91:293-301. doi: 10.1016/j.freeradbiomed.2015.10.417. Epub 2015 Oct 23. [PubMed:26526764 ]
  5. LOTUS database [Link]