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Record Information
Version1.0
Created at2020-12-09 00:10:33 UTC
Updated at2021-07-15 16:45:27 UTC
NP-MRD IDNP0003077
Secondary Accession NumbersNone
Natural Product Identification
Common NameVerrucine A
Provided ByNPAtlasNPAtlas Logo
Description Verrucine A is found in Penicillium verrucosum. It was first documented in 1999 (PMID: 10579880). Based on a literature review very few articles have been published on 3-[(1S,4S)-1-benzyl-3-hydroxy-6-oxo-1H,4H,6H-pyrazino[2,1-b]quinazolin-4-yl]propanimidic acid.
Structure
Data?1624573718
Synonyms
ValueSource
3-[(1S,4S)-1-Benzyl-3-hydroxy-6-oxo-1H,4H,6H-pyrazino[2,1-b]quinazolin-4-yl]propanimidateGenerator
Chemical FormulaC21H20N4O3
Average Mass376.4160 Da
Monoisotopic Mass376.15354 Da
IUPAC Name3-[(1S,4S)-1-benzyl-3,6-dioxo-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazolin-4-yl]propanamide
Traditional Name3-[(1S,4S)-1-benzyl-3,6-dioxo-1H,2H,4H-pyrazino[2,1-b]quinazolin-4-yl]propanamide
CAS Registry NumberNot Available
SMILES
NC(=O)CC[C@@H]1N2C(=O)C3=CC=CC=C3N=C2[C@H](CC2=CC=CC=C2)NC1=O
InChI Identifier
InChI=1S/C21H20N4O3/c22-18(26)11-10-17-20(27)24-16(12-13-6-2-1-3-7-13)19-23-15-9-5-4-8-14(15)21(28)25(17)19/h1-9,16-17H,10-12H2,(H2,22,26)(H,24,27)/t16-,17-/m0/s1
InChI KeyLISCNUCDEMJKLE-IRXDYDNUSA-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
Penicillium verrucosumNPAtlas
Chemical Taxonomy
ClassificationNot classified
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
logP1.06ALOGPS
logP1.23ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.21ChemAxon
pKa (Strongest Basic)2.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.86 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity104.75 m³·mol⁻¹ChemAxon
Polarizability39.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA019031
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8984833
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10809528
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Larsen TO, Franzyk H, Jensen SR: UV-Guided isolation of verrucines A and B, novel quinazolines from penicillium verrucosum structurally related to anacine from penicilliumaurantiogriseum J Nat Prod. 1999 Nov;62(11):1578-80. doi: 10.1021/np990251p. [PubMed:10579880 ]