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Record Information
Version1.0
Created at2022-09-02 15:18:52 UTC
Updated at2022-09-02 15:18:52 UTC
NP-MRD IDNP0157829
Secondary Accession NumbersNone
Natural Product Identification
Common Name{3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate
Description2-(Acetoxyamino)-3-methylimidazo[4,5-f]quinoline, also known as N-acetoxy-iq, belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. 2-(Acetoxyamino)-3-methylimidazo[4,5-f]quinoline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. {3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate is found in Apis cerana. It was first documented in 1994 (PMID: 7696529). Based on a literature review a significant number of articles have been published on 2-(acetoxyamino)-3-methylimidazo[4,5-f]quinoline (PMID: 36055769) (PMID: 36055768) (PMID: 36055767) (PMID: 36055766) (PMID: 36055765) (PMID: 36055763).
Structure
Thumb
Synonyms
ValueSource
N-Acetoxy-iqChEBI
Chemical FormulaC13H12N4O2
Average Mass256.2650 Da
Monoisotopic Mass256.09603 Da
IUPAC Name{3-methyl-3H-imidazo[4,5-f]quinolin-2-yl}amino acetate
Traditional Name{3-methylimidazo[4,5-f]quinolin-2-yl}amino acetate
CAS Registry NumberNot Available
SMILES
CN1C(NOC(C)=O)=NC2=C1C=CC1=NC=CC=C21
InChI Identifier
InChI=1S/C13H12N4O2/c1-8(18)19-16-13-15-12-9-4-3-7-14-10(9)5-6-11(12)17(13)2/h3-7H,1-2H3,(H,15,16)
InChI KeyZNLLBBZONQYLII-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
Apis ceranaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassNot Available
Direct ParentQuinolines and derivatives
Alternative Parents
Substituents
  • Quinoline
  • N-acetoxyarylamine
  • Benzimidazole
  • N-substituted imidazole
  • Pyridine
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Acetate salt
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic salt
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP1.87ALOGPS
logP1.98ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)13.13ChemAxon
pKa (Strongest Basic)4.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.04 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity69.4 m³·mol⁻¹ChemAxon
Polarizability26.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID129282
KEGG Compound IDC20290
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound146575
PDB IDNot Available
ChEBI ID133918
Good Scents IDNot Available
References
General References
  1. Pays E, Radwanska M, Magez S: The Pathogenesis of African Trypanosomiasis. Annu Rev Pathol. 2022 Sep 2. doi: 10.1146/annurev-pathmechdis-031621-025153. [PubMed:36055769 ]
  2. Khan K, Van Aken O: The colonisation of land was a likely driving force for the evolution of mitochondrial retrograde signalling in plants. J Exp Bot. 2022 Sep 3. pii: 6687801. doi: 10.1093/jxb/erac351. [PubMed:36055768 ]
  3. Authors unspecified: Erratum. Br J Dermatol. 2022 Sep;187(3):451. doi: 10.1111/bjd.21748. [PubMed:36055767 ]
  4. Authors unspecified: BAD and BPG guidelines for narrowband ultraviolet B phototherapy 2022. Br J Dermatol. 2022 Sep;187(3):vi. doi: 10.1111/bjd.21734. [PubMed:36055766 ]
  5. Sprecher E: What do rare and common have in common? Br J Dermatol. 2022 Sep;187(3):279-280. doi: 10.1111/bjd.21632. [PubMed:36055765 ]
  6. Dias BGC, Santos FAP, Meschiatti M, Brixner BM, Almeida AA, Queiroz O, Cappellozza BI: Effects of feeding different probiotic types on metabolic, performance, and carcass responses of Bos indicus feedlot cattle offered a high-concentrate diet. J Anim Sci. 2022 Oct 1;100(10). pii: 6687795. doi: 10.1093/jas/skac289. [PubMed:36055763 ]
  7. Authors unspecified: Revolutionizing Atopic Dermatitis, 9-11 April 2022. Br J Dermatol. 2022 Sep;187(3):e80-e155. doi: 10.1111/bjd.21666. [PubMed:36055764 ]
  8. Wang B, Lv R, Zhang Z, Yang C, Xun H, Liu B, Gong L: Homoeologous exchange enables rapid evolution of tolerance to salinity and hyper-osmotic stresses in a synthetic allotetraploid wheat. J Exp Bot. 2022 Dec 8;73(22):7488-7502. doi: 10.1093/jxb/erac355. [PubMed:36055762 ]
  9. Horwitz JK, Kaldas FM: CAQ Corner: Technical considerations in liver transplantation (101 for hepatologists). Liver Transpl. 2023 Feb 1;29(2):217-225. doi: 10.1002/lt.26556. Epub 2023 Jan 17. [PubMed:36055761 ]
  10. Turesky RJ, Markovic J: DNA adduct formation of the food carcinogen 2-amino-3-methylimidazo[4,5- f]quinoline at the C-8 and N2 atoms of guanine. Chem Res Toxicol. 1994 Nov-Dec;7(6):752-61. doi: 10.1021/tx00042a007. [PubMed:7696529 ]
  11. LOTUS database [Link]