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Showing NP-Card for (5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one (NP0299732)

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Record Information
Version2.0
Created at2022-09-10 11:43:46 UTC
Updated at2022-09-10 11:43:46 UTC
NP-MRD IDNP0299732
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one
Description5(S)-[1-(1(S)-hydroxybut-2-enyl)]-furan-2-one belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one is found in Nigrospora sacchari, Hypomyces chrysospermus and Streptomyces griseoviridis. Based on a literature review very few articles have been published on 5(S)-[1-(1(S)-hydroxybut-2-enyl)]-furan-2-one.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0299732 ((5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one)


  Mrv1652309102213432D          

 11 11  0  0  1  0            999 V2000
    2.7112    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  4  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
Download

3D MOL for NP0299732 ((5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
    3.5520   -0.2515    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297   -0.0615   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1071   -0.0289   -0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    0.1661   -1.0391 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2220    1.2288   -1.9240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2876    0.5691   -0.2689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8035   -0.5136    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0033   -0.9094    0.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757   -0.1160   -0.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4275   -0.1464   -1.6628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330    0.7526   -1.2053 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2434    0.6032    0.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2956   -0.1500    1.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686   -1.1928    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553    0.0566   -1.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1449    0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2240   -0.7714   -1.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3117    2.0349   -1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.5149    0.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3011   -0.9570    1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6399   -1.6828    0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  4 17  1  6
  5 18  1  0
  6 19  1  1
  8 21  1  0
  7 20  1  0
M  END
Download

3D SDF for NP0299732 ((5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one)


  Mrv1652309102213432D          

 11 11  0  0  1  0            999 V2000
    2.7112    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  4  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299732

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O3/c1-2-3-6(9)7-4-5-8(10)11-7/h2-7,9H,1H3/b3-2+/t6-,7-/m0/s1

> <INCHI_KEY>
SMKPKIFBQCUYGS-VHJVCUAWSA-N

> <FORMULA>
C8H10O3

> <MOLECULAR_WEIGHT>
154.165

> <EXACT_MASS>
154.062994182

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.495821497274529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-[(1S,2E)-1-hydroxybut-2-en-1-yl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
1.0839325346666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.441456187223693

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.130197696823216

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3447196677559745

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
41.716300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-[(1S,2E)-1-hydroxybut-2-en-1-yl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0299732 ((5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one)

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PDB for NP0299732 ((5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.061   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.727   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0299732 ((5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one)
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SMILES for NP0299732 ((5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one)
C\C=C\[C@H](O)[C@H]1OC(=O)C=C1
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INCHI for NP0299732 ((5s)-5-[(1s,2e)-1-hydroxybut-2-en-1-yl]-5h-furan-2-one)
InChI=1S/C8H10O3/c1-2-3-6(9)7-4-5-8(10)11-7/h2-7,9H,1H3/b3-2+/t6-,7-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H10O3
Average Mass154.1650 Da
Monoisotopic Mass154.06299 Da
IUPAC Name(5S)-5-[(1S,2E)-1-hydroxybut-2-en-1-yl]-2,5-dihydrofuran-2-one
Traditional Name(5S)-5-[(1S,2E)-1-hydroxybut-2-en-1-yl]-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
C\C=C\[C@H](O)[C@H]1OC(=O)C=C1
InChI Identifier
InChI=1S/C8H10O3/c1-2-3-6(9)7-4-5-8(10)11-7/h2-7,9H,1H3/b3-2+/t6-,7-/m0/s1
InChI KeySMKPKIFBQCUYGS-VHJVCUAWSA-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
Nigrospora sacchariLOTUS Database
Sepedonium chrysospermumLOTUS Database
Streptomyces griseoviridisLOTUS 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
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • 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
logP1.08ChemAxon
pKa (Strongest Acidic)6.13ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.72 m³·mol⁻¹ChemAxon
Polarizability15.5 ųChemAxon
Number of Rings1ChemAxon
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 IDNot Available
Chemspider ID8996070  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10820768  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]