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Record Information
Version1.0
Created at2020-12-09 00:51:07 UTC
Updated at2021-07-15 16:47:02 UTC
NP-MRD IDNP0003661
Secondary Accession NumbersNone
Natural Product Identification
Common NameTryptoquivaline
Provided ByNPAtlasNPAtlas Logo
Description Tryptoquivaline is found in Aspergillus, Aspergillus clavatus, Aspergillus clavatus (NRRL5890) and Aspergillus fumigatus. It was first documented in 1975 (PMID: 1133368). Based on a literature review very few articles have been published on (1S)-1-{3-[(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxo-3,4-dihydroquinazolin-2-yl}-2-methylpropyl acetate.
Structure
Data?1624573870
Synonyms
ValueSource
(1S)-1-{3-[(4'r,9S,9as)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxo-3,4-dihydroquinazolin-2-yl}-2-methylpropyl acetic acidGenerator
Tryproquivaline m (2's-(2'alpha,9'alpha(4R*(s*)),9'abeta))-isomerMeSH
Tryproquivaline D (2's-(2'alpha,9'alpha(4R*(s*)),9'abeta))-isomerMeSH
Tryproquivaline L (9'r-(9'alpha(r*),9'abeta))-isomerMeSH
Tryproquivaline m (2's-(2'alpha,9'alpha(4S*(s*)),9'abeta))-isomerMeSH
Fumitremorgin CMeSH
Tryproquivaline L (9'r-(9'alpha(s*),9'abeta))-isomerMeSH
Tryproquivaline N (2's-(2'alpha,9'alpha(r*),9'abeta))-isomerMeSH
Chemical FormulaC29H30N4O7
Average Mass546.5800 Da
Monoisotopic Mass546.21145 Da
IUPAC Name(1S)-1-{3-[(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-1,2,3,9a-tetrahydrospiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxo-3,4-dihydroquinazolin-2-yl}-2-methylpropyl acetate
Traditional Name(1S)-1-{3-[(4'R,9S,9aS)-1-hydroxy-2,2-dimethyl-3,5'-dioxo-9aH-spiro[imidazo[1,2-a]indole-9,2'-oxolane]-4'-yl]-4-oxoquinazolin-2-yl}-2-methylpropyl acetate
CAS Registry NumberNot Available
SMILES
CC(C)[C@H](OC(C)=O)C1=NC2=CC=CC=C2C(=O)N1[C@@H]1C[C@@]2(OC1=O)[C@@H]1N(O)C(C)(C)C(=O)N1C1=CC=CC=C21
InChI Identifier
InChI=1S/C29H30N4O7/c1-15(2)22(39-16(3)34)23-30-19-12-8-6-10-17(19)24(35)31(23)21-14-29(40-25(21)36)18-11-7-9-13-20(18)32-26(29)33(38)28(4,5)27(32)37/h6-13,15,21-22,26,38H,14H2,1-5H3/t21-,22+,26+,29+/m1/s1
InChI KeyCYNVLFGDEQQUPE-LDWWEUSWSA-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
Aspergillus-
Aspergillus clavatusNPAtlas
Aspergillus clavatus (NRRL5890)Fungi
Aspergillus fumigatusFungi
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
logP2.44ALOGPS
logP2.72ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)1.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area129.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity142.18 m³·mol⁻¹ChemAxon
Polarizability56.65 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA015403
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID97176
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound108075
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Clardy J, Springer JP, Buchi G, Matsuo K, Wightman R: Letter: Tryptoquivaline and tryptoquivalone, two tremorgenic metabolites of aspergillus clavatus. J Am Chem Soc. 1975 Feb 5;97(3):663-5. doi: 10.1021/ja00836a045. [PubMed:1133368 ]