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Showing NP-Card for (3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one (NP0146742)

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Record Information
Version2.0
Created at2022-09-02 02:12:18 UTC
Updated at2022-09-02 02:12:19 UTC
NP-MRD IDNP0146742
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one
DescriptionOxysporone belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one is found in Pestalotiopsis longiseta. (3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one was first documented in 2012 (PMID: 22805506). Based on a literature review a small amount of articles have been published on Oxysporone (PMID: 32603933) (PMID: 29193363) (PMID: 23427901) (PMID: 22326509).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0146742 ((3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one)


  Mrv1652309022204122D          

 11 12  0  0  1  0            999 V2000
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
  5 11  1  6  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0146742 ((3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one)

     RDKit          3D

 19 20  0  0  0  0  0  0  0  0999 V2000
    3.6285   -0.6915   -0.6679 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357   -0.1441   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585   -0.6328    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2537   -0.4691   -0.1850 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5188    0.7988   -0.9418 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2115    1.9006   -0.3927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5704    1.6569   -0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594    0.5143    0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257   -0.4567    0.7122 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4512   -1.7411    0.8816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9255    1.0094   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4715    0.0750    1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7178   -1.6723    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2139   -1.2924   -0.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2890    0.6968   -2.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3634    2.3437   -0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    0.2912    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5692   -0.1670    1.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0287   -2.0197    0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5 11  1  0
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  9  1  0
  4  5  1  0
 10 19  1  0
  9 18  1  1
  8 17  1  0
  7 16  1  0
  5 15  1  6
  3 12  1  0
  3 13  1  0
  4 14  1  6
M  END
Download

3D SDF for NP0146742 ((3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one)


  Mrv1652309022204122D          

 11 12  0  0  1  0            999 V2000
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
  5 11  1  6  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C=CO[C@H]2OC(=O)C[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O4/c8-5-1-2-10-7-4(5)3-6(9)11-7/h1-2,4-5,7-8H,3H2/t4-,5+,7-/m0/s1

> <INCHI_KEY>
RJIMODGWTUNSPV-BFHQHQDPSA-N

> <FORMULA>
C7H8O4

> <MOLECULAR_WEIGHT>
156.137

> <EXACT_MASS>
156.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.856848586123968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,4R,7aS)-4-hydroxy-2H,3H,3aH,4H,7aH-furo[2,3-b]pyran-2-one

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
-0.30764112800000026

> <ALOGPS_LOGS>
0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.301030726371483

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1045291602851135

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
34.733200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4R,7aS)-4-hydroxy-3H,3aH,4H,7aH-furo[2,3-b]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0146742 ((3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one)

Download
PDB for NP0146742 ((3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.530   0.237   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0146742 ((3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one)
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SMILES for NP0146742 ((3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one)
O[C@@H]1C=CO[C@H]2OC(=O)C[C@@H]12
Download
INCHI for NP0146742 ((3as,4r,7as)-4-hydroxy-3h,3ah,4h,7ah-furo[2,3-b]pyran-2-one)
InChI=1S/C7H8O4/c8-5-1-2-10-7-4(5)3-6(9)11-7/h1-2,4-5,7-8H,3H2/t4-,5+,7-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H8O4
Average Mass156.1370 Da
Monoisotopic Mass156.04226 Da
IUPAC Name(3aS,4R,7aS)-4-hydroxy-2H,3H,3aH,4H,7aH-furo[2,3-b]pyran-2-one
Traditional Name(3aS,4R,7aS)-4-hydroxy-3H,3aH,4H,7aH-furo[2,3-b]pyran-2-one
CAS Registry NumberNot Available
SMILES
O[C@@H]1C=CO[C@H]2OC(=O)C[C@@H]12
InChI Identifier
InChI=1S/C7H8O4/c8-5-1-2-10-7-4(5)3-6(9)11-7/h1-2,4-5,7-8H,3H2/t4-,5+,7-/m0/s1
InChI KeyRJIMODGWTUNSPV-BFHQHQDPSA-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
Pestalotiopsis longisetaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassFuropyrans  
Sub ClassNot Available
Direct ParentFuropyrans  
Alternative Parents
Substituents
  • Furopyran
    • 

  • Gamma butyrolactone
    • 

  • Pyran
    • 

  • Furan
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Acetal
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • 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
logP-0.46ALOGPS
logP-0.31ChemAxon
logS0.36ALOGPS
pKa (Strongest Acidic)14.3ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.73 m³·mol⁻¹ChemAxon
Polarizability13.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00023991  
Chemspider ID61604698  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14841096  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Luo du Q, Zhang L, Shi BZ, Song XM: Two new oxysporone derivatives from the fermentation broth of the endophytic plant fungus Pestalotiopsis karstenii isolated from stems of Camellia sasanqua. Molecules. 2012 Jul 17;17(7):8554-60. doi: 10.3390/molecules17078554. [PubMed:22805506  ] 
  2. Xie J, Wei JG, Wang KW, Luo J, Wu YJ, Luo JT, Yang XH, Yang XB: Three phytotoxins produced by Neopestalotiopsis clavispora, the causal agent of ring spot on Kadsura coccinea. Microbiol Res. 2020 Sep;238:126531. doi: 10.1016/j.micres.2020.126531. Epub 2020  Jun 24. [PubMed:32603933  ] 
  3. Nurunnabi TR, Nahar L, Al-Majmaie S, Rahman SMM, Sohrab MH, Billah MM, Ismail FMD, Rahman MM, Sharples GP, Sarker SD: Anti-MRSA activity of oxysporone and xylitol from the endophytic fungus Pestalotia sp. growing on the Sundarbans mangrove plant Heritiera fomes. Phytother Res. 2018 Feb;32(2):348-354. doi: 10.1002/ptr.5983. Epub 2017 Nov 29. [PubMed:29193363  ] 
  4. Mazzeo G, Santoro E, Andolfi A, Cimmino A, Troselj P, Petrovic AG, Superchi S, Evidente A, Berova N: Absolute configurations of fungal and plant metabolites by chiroptical methods. ORD, ECD, and VCD studies on phyllostin, scytolide, and oxysporone. J Nat Prod. 2013 Apr 26;76(4):588-99. doi: 10.1021/np300770s. Epub 2013 Feb 21. [PubMed:23427901  ] 
  5. Evidente A, Masi M, Linaldeddu BT, Franceschini A, Scanu B, Cimmino A, Andolfi A, Motta A, Maddau L: Afritoxinones A and B, dihydrofuropyran-2-ones produced by Diplodia africana the causal agent of branch dieback on Juniperus phoenicea. Phytochemistry. 2012 May;77:245-50. doi: 10.1016/j.phytochem.2012.01.011. Epub  2012 Feb 10. [PubMed:22326509  ] 
  6. LOTUS database [Link]