Np mrd loader

Record Information
Version2.0
Created at2022-09-08 23:10:03 UTC
Updated at2022-09-08 23:10:03 UTC
NP-MRD IDNP0275427
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2r,5s,6r)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
DescriptionAsperpentyn belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). (1s,2r,5s,6r)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol is found in Aspergillus duricaulis and Rhizophora apiculata. (1s,2r,5s,6r)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol was first documented in 2009 (PMID: 19115846). Based on a literature review a small amount of articles have been published on Asperpentyn (PMID: 35628710) (PMID: 32343875) (PMID: 32174195) (PMID: 26270650).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H12O3
Average Mass192.2140 Da
Monoisotopic Mass192.07864 Da
IUPAC Name(1S,2R,5S,6R)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
Traditional Name(1S,2R,5S,6R)-3-(3-methylbut-3-en-1-yn-1-yl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
CAS Registry NumberNot Available
SMILES
CC(=C)C#CC1=C[C@H](O)[C@H]2O[C@H]2[C@@H]1O
InChI Identifier
InChI=1S/C11H12O3/c1-6(2)3-4-7-5-8(12)10-11(14-10)9(7)13/h5,8-13H,1H2,2H3/t8-,9+,10+,11-/m0/s1
InChI KeyKPEYCTJGQFOOBS-ZDCRXTMVSA-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
Aspergillus duricaulisLOTUS Database
Rhizophora apiculataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentSecondary alcohols
Alternative Parents
Substituents
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP0.27ChemAxon
pKa (Strongest Acidic)13.04ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.43 m³·mol⁻¹ChemAxon
Polarizability20.23 ųChemAxon
Number of Rings2ChemAxon
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 ID9655773
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11480953
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Li J, Park S, Miller RL, Lee D: Tandem enyne metathesis-metallotropic [1,3]-shift for a concise total syntheses of (+)-asperpentyn, (-)-harveynone, and (-)-tricholomenyn A. Org Lett. 2009 Feb 5;11(3):571-4. doi: 10.1021/ol802675j. [PubMed:19115846 ]
  2. Zhuravleva OI, Oleinikova GK, Antonov AS, Kirichuk NN, Pelageev DN, Rasin AB, Menshov AS, Popov RS, Kim NY, Chingizova EA, Chingizov AR, Volchkova OO, von Amsberg G, Dyshlovoy SA, Yurchenko EA, Guzhova IV, Yurchenko AN: New Antibacterial Chloro-Containing Polyketides from the Alga-Derived Fungus Asteromyces cruciatus KMM 4696. J Fungi (Basel). 2022 Apr 27;8(5):454. doi: 10.3390/jof8050454. [PubMed:35628710 ]
  3. Chen YR, Naresh A, Liang SY, Lin CH, Chein RJ, Lin HC: Discovery of a Dual Function Cytochrome P450 that Catalyzes Enyne Formation in Cyclohexanoid Terpenoid Biosynthesis. Angew Chem Int Ed Engl. 2020 Aug 3;59(32):13537-13541. doi: 10.1002/anie.202004435. Epub 2020 Jun 2. [PubMed:32343875 ]
  4. Polli AD, Ribeiro MADS, Garcia A, Polonio JC, Santos CM, Silva AA, Orlandelli RC, Castro JC, Abreu-Filho BA, Cabral MRP, Sarragiotto MH, Pamphile JA, Azevedo JL: Secondary metabolites of Curvularia sp. G6-32, an endophyte of Sapindus saponaria, with antioxidant and anticholinesterasic properties. Nat Prod Res. 2021 Nov;35(21):4148-4153. doi: 10.1080/14786419.2020.1739681. Epub 2020 Mar 16. [PubMed:32174195 ]
  5. Lan P, White LE, Taher ES, Guest PE, Banwell MG, Willis AC: Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A. J Nat Prod. 2015 Aug 28;78(8):1963-8. doi: 10.1021/acs.jnatprod.5b00304. Epub 2015 Aug 13. [PubMed:26270650 ]
  6. LOTUS database [Link]