Np mrd loader

Showing NP-Card for Aspyrone (NP0140949)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2022-06-29 22:00:00 UTC
Updated at2022-06-29 22:00:00 UTC
NP-MRD IDNP0140949
Secondary Accession NumbersNone
Natural Product Identification
Common NameAspyrone
DescriptionAspyrone belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Aspyrone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Aspyrone is found in Aspergillus melleus, Aspergillus ochraceus and Aspergillus westerdijkiae. It was first documented in 1995 (PMID: 8534985). Based on a literature review a small amount of articles have been published on aspyrone (PMID: 18661951) (PMID: 31284571) (PMID: 19589392) (PMID: 28958507).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0140949 (Aspyrone)


  Mrv1652306302200002D          

 13 14  0  0  1  0            999 V2000
    0.7145    6.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.4901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    5.0776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    4.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.0151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270    2.3007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    2.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  9  5  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  6  0  0  0
  3 13  1  1  0  0  0
M  END
Download

3D MOL for NP0140949 (Aspyrone)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
   -3.9039    0.0523    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492   -0.5859   -0.2991 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1761   -1.7586    0.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -0.6396    0.7268 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2056   -0.2565    0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    0.7717    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263    1.2231    0.2112 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5785    2.3372   -0.6196 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4688    0.0987   -0.4946 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9156   -0.8889    0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6247   -0.5820   -1.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3889   -0.9909   -0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2113   -1.9987   -1.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    0.7965   -0.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7101    0.6599    1.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7154   -0.6458    0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3979   -0.4554   -1.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327   -0.3563    1.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    1.3405    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2988    1.5663    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6766    3.1919   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3509    0.5327   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6405   -0.3803    1.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024   -1.7431    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0384   -1.2888    1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
  4  2  1  0
 12  5  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  6
  4 18  1  1
  6 19  1  0
  7 20  1  1
  8 21  1  0
  9 22  1  6
 10 23  1  0
 10 24  1  0
 10 25  1  0
M  END
Download

3D SDF for NP0140949 (Aspyrone)


  Mrv1652306302200002D          

 13 14  0  0  1  0            999 V2000
    0.7145    6.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.4901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    5.0776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    4.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.8401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.0151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270    2.3007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    2.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  9  5  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  6  0  0  0
  3 13  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@H]1C1=C[C@H](O)[C@@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O4/c1-4-7(10)3-6(9(11)13-4)8-5(2)12-8/h3-5,7-8,10H,1-2H3/t4-,5+,7+,8-/m1/s1

> <INCHI_KEY>
RCAULRNMJFUWRP-HETMPLHPSA-N

> <FORMULA>
C9H12O4

> <MOLECULAR_WEIGHT>
184.191

> <EXACT_MASS>
184.073558866

$$$$
Download

3D-SDF for NP0140949 (Aspyrone)

Download
PDB for NP0140949 (Aspyrone)
HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334  11.788   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  10.248   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   9.478   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   7.938   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   7.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   7.938   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   7.168   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.000   9.478   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334   5.628   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104   4.295   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.564   4.295   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.437   3.525   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  10.248   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2                                                       
CONECT    9    5   10   11                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    9                                                       
CONECT   12   10                                                            
CONECT   13    3                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Download
3D PDB for NP0140949 (Aspyrone)
Download
SMILES for NP0140949 (Aspyrone)
C[C@@H]1O[C@H]1C1=C[C@H](O)[C@@H](C)OC1=O
Download
INCHI for NP0140949 (Aspyrone)
InChI=1S/C9H12O4/c1-4-7(10)3-6(9(11)13-4)8-5(2)12-8/h3-5,7-8,10H,1-2H3/t4-,5+,7+,8-/m1/s1
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC9H12O4
Average Mass184.1910 Da
Monoisotopic Mass184.07356 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C[C@@H]1O[C@H]1C1=C[C@H](O)[C@@H](C)OC1=O
InChI Identifier
InChI=1S/C9H12O4/c1-4-7(10)3-6(9(11)13-4)8-5(2)12-8/h3-5,7-8,10H,1-2H3/t4-,5+,7+,8-/m1/s1
InChI KeyRCAULRNMJFUWRP-HETMPLHPSA-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 melleusLOTUS Database
Aspergillus ochraceusLOTUS Database
Aspergillus westerdijkiaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentDihydropyranones  
Alternative Parents
Substituents
  • Dihydropyranone
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00014978  
Chemspider ID146667  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound167653  
PDB IDNot Available
ChEBI ID156387  
Good Scents IDNot Available
References
General References
  1. Zhang D, Yang X, Kang JS, Choi HD, Son BW: Chlorohydroaspyrones A and B, antibacterial aspyrone derivatives from the marine-derived fungus Exophiala sp. J Nat Prod. 2008 Aug;71(8):1458-60. doi: 10.1021/np800107c. Epub 2008 Jul 29. [PubMed:18661951  ] 
  2. Fan Y, Zhou Y, Du Y, Wang Y, Fu P, Zhu W: Circumdatin-Aspyrone Conjugates from the Coral-Associated Aspergillus ochraceus LCJ11-102. Mar Drugs. 2019 Jul 6;17(7). pii: md17070400. doi: 10.3390/md17070400. [PubMed:31284571  ] 
  3. Bacha N, Dao HP, Atoui A, Mathieu F, O'Callaghan J, Puel O, Liboz T, Dobson AD, Lebrihi A: Cloning and characterization of novel methylsalicylic acid synthase gene involved in the biosynthesis of isoasperlactone and asperlactone in Aspergillus westerdijkiae. Fungal Genet Biol. 2009 Oct;46(10):742-9. doi: 10.1016/j.fgb.2009.07.002. Epub  2009 Jul 7. [PubMed:19589392  ] 
  4. Saldan NC, Almeida RTR, Avincola A, Porto C, Galuch MB, Magon TFS, Pilau EJ, Svidzinski TIE, Oliveira CC: Development of an analytical method for identification of Aspergillus flavus based on chemical markers using HPLC-MS. Food Chem. 2018 Feb 15;241:113-121. doi: 10.1016/j.foodchem.2017.08.065. Epub  2017 Aug 24. [PubMed:28958507  ] 
  5. Sugiyama T, Murayama T, Yamashita K, Oritani T: Synthesis of chiral aspyrone, a multi-functional dihydropyranone antibiotic. Biosci Biotechnol Biochem. 1995 Oct;59(10):1921-4. doi: 10.1271/bbb.59.1921. [PubMed:8534985  ]