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Showing NP-Card for (5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one (NP0330415)

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Record Information
Version1.0
Created at2022-09-12 15:44:55 UTC
Updated at2022-09-12 15:44:55 UTC
NP-MRD IDNP0330415
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one
DescriptionAporpinone B belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one is found in Elmerina caryae. It was first documented in 2011 (PMID: 21477823). Based on a literature review very few articles have been published on Aporpinone B.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0330415 ((5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one)


  Mrv1652309122217442D          

 14 15  0  0  0  0            999 V2000
    1.0857    6.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062    6.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187    6.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    6.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    5.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    5.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    4.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    3.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3389    2.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5139    2.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6409    5.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3553    5.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4582    5.5064    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  3  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
  2 14  1  0  0  0  0
M  END
Download

3D MOL for NP0330415 ((5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one)

     RDKit          3D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -1.9187   -3.1878    1.8048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -2.1237    1.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -1.4192    0.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8276   -0.3453    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3678   -0.3115   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5762    0.5763   -0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8599    0.4066   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0552    0.2538   -0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.0561   -0.3815 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9893   -0.7683    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    0.6543    0.6834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1600    1.7418   -1.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132    2.9496   -0.7044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846   -1.4293    0.6739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2369   -1.6831    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4857    0.4006   -0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652   -0.0096   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584   -1.2683    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067   -1.1085    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2425    1.7492   -1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730    1.7804   -2.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631    3.0859    0.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12  6  1  0
  6  7  1  0
  7  8  3  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6  5  2  0
  5 14  1  0
 14  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
 11  9  1  0
  4  5  1  0
 13 22  1  0
 12 20  1  0
 12 21  1  0
  9 17  1  6
 10 18  1  0
 10 19  1  0
  3 15  1  0
  4 16  1  0
M  END
Download

3D SDF for NP0330415 ((5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one)


  Mrv1652309122217442D          

 14 15  0  0  0  0            999 V2000
    1.0857    6.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062    6.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3187    6.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1257    6.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119    5.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    5.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    4.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    3.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3389    2.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5139    2.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6409    5.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3553    5.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4582    5.5064    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  3  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330415

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC\C(C#CC1CO1)=C1\OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O4/c11-5-7(1-2-8-6-13-8)9-3-4-10(12)14-9/h3-4,8,11H,5-6H2/b9-7+

> <INCHI_KEY>
WYMTWRGLKSMOPA-VQHVLOKHSA-N

> <FORMULA>
C10H8O4

> <MOLECULAR_WEIGHT>
192.17

> <EXACT_MASS>
192.042258738

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.7663071952138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
-0.1695120113333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.612169960748332

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9684359676023444

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
50.5308

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0330415 ((5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one)

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PDB for NP0330415 ((5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       2.027  11.262   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.558  11.423   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.328  12.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.835  12.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.996  10.905   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.329  10.135   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.329   8.595   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.329   7.055   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.329   5.515   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.099   4.181   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.559   4.181   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.663  10.905   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.997  10.135   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.589  10.279   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   11                                                       
CONECT   11   10    9                                                       
CONECT   12    6   13                                                       
CONECT   13   12                                                            
CONECT   14    5    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0330415 ((5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one)
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SMILES for NP0330415 ((5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one)
OC\C(C#CC1CO1)=C1\OC(=O)C=C1
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INCHI for NP0330415 ((5e)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one)
InChI=1S/C10H8O4/c11-5-7(1-2-8-6-13-8)9-3-4-10(12)14-9/h3-4,8,11H,5-6H2/b9-7+
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H8O4
Average Mass192.1700 Da
Monoisotopic Mass192.04226 Da
IUPAC Name(5E)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]-2,5-dihydrofuran-2-one
Traditional Name(5E)-5-[1-hydroxy-4-(oxiran-2-yl)but-3-yn-2-ylidene]furan-2-one
CAS Registry NumberNot Available
SMILES
OC\C(C#CC1CO1)=C1\OC(=O)C=C1
InChI Identifier
InChI=1S/C10H8O4/c11-5-7(1-2-8-6-13-8)9-3-4-10(12)14-9/h3-4,8,11H,5-6H2/b9-7+
InChI KeyWYMTWRGLKSMOPA-VQHVLOKHSA-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
Elmerina caryaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDihydrofurans  
Sub ClassFuranones  
Direct ParentButenolides  
Alternative Parents
Substituents
  • 2-furanone
    • 

  • Enol ester
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • 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
logP-0.17ChemAxon
pKa (Strongest Acidic)14.61ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.53 m³·mol⁻¹ChemAxon
Polarizability18.77 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 IDC00035910  
Chemspider ID8279554  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10104027  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Jiang MY, Li Y, Wang F, Liu JK: Isoprenylated cyclohexanoids from the basidiomycete Hexagonia speciosa. Phytochemistry. 2011 Jun;72(9):923-8. doi: 10.1016/j.phytochem.2011.03.011. Epub  2011 Apr 7. [PubMed:21477823  ] 
  2. LOTUS database [Link]