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Record Information
Version1.0
Created at2021-01-06 07:00:33 UTC
Updated at2021-07-15 17:37:08 UTC
NP-MRD IDNP0021734
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcrylamidine
Provided ByNPAtlasNPAtlas Logo
DescriptionAcrylamidine belongs to the class of organic compounds known as carboxamidines. These are carboxylic acid derivatives containing the amidine group. Acrylamidine is found in Streptomyces sp. It was first documented in 1968 (PMID: 5751268). Based on a literature review very few articles have been published on acrylamidine (PMID: 28783355) (PMID: 23642149) (PMID: 16307887) (PMID: 15493957).
Structure
Data?1624506921
SynonymsNot Available
Chemical FormulaC3H6N2
Average Mass70.0950 Da
Monoisotopic Mass70.05310 Da
IUPAC Nameprop-2-enimidamide
Traditional Nameprop-2-enimidamide
CAS Registry NumberNot Available
SMILES
NC(=N)C=C
InChI Identifier
InChI=1S/C3H6N2/c1-2-3(4)5/h2H,1H2,(H3,4,5)
InChI KeyAXPUQAAUHKSVKR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces sp.NPAtlas
Species Where Detected
Species NameSourceReference
Streptomyces sp. D274-2KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboxamidines. These are carboxylic acid derivatives containing the amidine group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmidines
Direct ParentCarboxamidines
Alternative Parents
Substituents
  • Carboximidamide
  • Carboxylic acid amidine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP-0.71ALOGPS
logP-0.2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)12.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.87 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.71 m³·mol⁻¹ChemAxon
Polarizability7.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA016478
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00018751
Chemspider ID2722428
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3481477
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yagishita K, Utahara R, Maeda K, Hamada M, Umezawa H: Acrylamidine, an anti-fungal substance produced by a Streptomyces. J Antibiot (Tokyo). 1968 Jul;21(7):444-50. doi: 10.7164/antibiotics.21.444. [PubMed:5751268 ]
  2. Prasad SS, Senthilkumar S, Srivastava A, Baskaran S: Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars. Org Lett. 2017 Aug 18;19(16):4403-4406. doi: 10.1021/acs.orglett.7b02175. Epub 2017 Aug 7. [PubMed:28783355 ]
  3. Yan X, Liao J, Lu Y, Liu J, Zeng Y, Cai Q: Pd-catalyzed one-pot synthesis of polysubstituted acrylamidines from isocyanides, diazo compounds, and imines. Org Lett. 2013 May 17;15(10):2478-81. doi: 10.1021/ol4009552. Epub 2013 May 3. [PubMed:23642149 ]
  4. Thominiaux C, de Bruin B, Bramoulle Y, Hinnen F, Demphel S, Valette H, Bottlaender M, Besret L, Kassiou M, Dolle F: Radiosynthesis of (E)-N-(2-[11C]methoxybenzyl)-3-phenyl-acrylamidine, a novel subnanomolar NR2B subtype-selective NMDA receptor antagonist. Appl Radiat Isot. 2006 Mar;64(3):348-54. doi: 10.1016/j.apradiso.2005.08.005. Epub 2005 Nov 22. [PubMed:16307887 ]
  5. Celewicz L, Mayer M, Shetlar MD: The photochemistry of thymidylyl-(3'-5')-5-methyl-2'-deoxycytidine in aqueous solution. Photochem Photobiol. 2005 Mar-Apr;81(2):404-18. doi: 10.1562/2004-06-15-ra-201.1. [PubMed:15493957 ]