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Record Information
Version1.0
Created at2020-09-23 01:59:07 UTC
Updated at2021-08-10 02:55:48 UTC
NP-MRD IDNP0001625
Secondary Accession NumbersNone
Natural Product Identification
Common NameDemethylasterriquinone B1
Provided ByNPAtlasNPAtlas Logo
DescriptionDemethylasterriquinone B1, also known as DMAQB-1, belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. Demethylasterriquinone B1 is found in Pseudomassaria and Pseudomassaria sp.. It was first documented in 1999 (PMID: 10320380). Based on a literature review a significant number of articles have been published on Demethylasterriquinone B1 (PMID: 30574832) (PMID: 29526571) (PMID: 17595071) (PMID: 17240464).
Structure
Data?1628564147
Synonyms
ValueSource
DMAQB-1HMDB
Demethyl-asterriquinone b1HMDB
Demethylasterriquinone b-1HMDB
Chemical FormulaC32H30N2O4
Average Mass506.6020 Da
Monoisotopic Mass506.22056 Da
IUPAC Name2,5-dihydroxy-3-[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]-6-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione
Traditional Name2,5-dihydroxy-3-[7-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]-6-[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
[H]OC1=C(C2=C([H])N([H])C3=C(C([H])=C([H])C([H])=C23)C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C(=O)C(O[H])=C(C2=C(N([H])C3=C([H])C([H])=C([H])C([H])=C23)C(C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=O
InChI Identifier
InChI=1S/C32H30N2O4/c1-6-32(4,5)31-23(20-11-7-8-13-22(20)34-31)25-29(37)27(35)24(28(36)30(25)38)21-16-33-26-18(15-14-17(2)3)10-9-12-19(21)26/h6-14,16,33-35,38H,1,15H2,2-5H3
InChI KeyXMGNJVXBPZAETK-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
PseudomassariaNPAtlas
Pseudomassaria sp.Fungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPrenylquinones
Alternative Parents
Substituents
  • Prenylbenzoquinone
  • Indole
  • Indole or derivatives
  • P-benzoquinone
  • Quinone
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Vinylogous acid
  • Ketone
  • Cyclic ketone
  • Azacycle
  • Enol
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • 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
logP4.67ALOGPS
logP6.85ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)5.42ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.18 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity153.47 m³·mol⁻¹ChemAxon
Polarizability57.31 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA000525
HMDB IDHMDB0250991
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00027037
Chemspider ID2281897
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3013166
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zhang B, Salituro G, Szalkowski D, Li Z, Zhang Y, Royo I, Vilella D, Diez MT, Pelaez F, Ruby C, Kendall RL, Mao X, Griffin P, Calaycay J, Zierath JR, Heck JV, Smith RG, Moller DE: Discovery of a small molecule insulin mimetic with antidiabetic activity in mice. Science. 1999 May 7;284(5416):974-7. doi: 10.1126/science.284.5416.974. [PubMed:10320380 ]
  2. Beard RS Jr, Hoettels BA, Meegan JE, Wertz TS, Cha BJ, Yang X, Oxford JT, Wu MH, Yuan SY: AKT2 maintains brain endothelial claudin-5 expression and selective activation of IR/AKT2/FOXO1-signaling reverses barrier dysfunction. J Cereb Blood Flow Metab. 2020 Feb;40(2):374-391. doi: 10.1177/0271678X18817512. Epub 2018 Dec 21. [PubMed:30574832 ]
  3. Deng T, Zhang Y, Wu Y, Ma P, Duan J, Qin W, Yang X, Chen M: Dibutyl phthalate exposure aggravates type 2 diabetes by disrupting the insulin-mediated PI3K/AKT signaling pathway. Toxicol Lett. 2018 Jun 15;290:1-9. doi: 10.1016/j.toxlet.2018.03.004. Epub 2018 Mar 8. [PubMed:29526571 ]
  4. Kim H, Deng L, Xiong X, Hunter WD, Long MC, Pirrung MC: Glyceraldehyde 3-phosphate dehydrogenase is a cellular target of the insulin mimic demethylasterriquinone B1. J Med Chem. 2007 Jul 26;50(15):3423-6. doi: 10.1021/jm070437i. Epub 2007 Jun 27. [PubMed:17595071 ]
  5. Shah DI, Singh M: Effect of demethylasterriquinone b1 in hypertension associated vascular endothelial dysfunction. Int J Cardiol. 2007 Sep 3;120(3):317-24. doi: 10.1016/j.ijcard.2006.10.006. Epub 2007 Jan 22. [PubMed:17240464 ]