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Showing NP-Card for (5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one (NP0284771)

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Record Information
Version2.0
Created at2022-09-09 12:38:33 UTC
Updated at2022-09-09 12:38:33 UTC
NP-MRD IDNP0284771
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one
Description(5Z)-5-[(2R,3R)-2,3-dihydroxybutylidene]-3-[(2R)-2-hydroxypropyl]-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Based on a literature review very few articles have been published on (5Z)-5-[(2R,3R)-2,3-dihydroxybutylidene]-3-[(2R)-2-hydroxypropyl]-2,5-dihydrofuran-2-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0284771 ((5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one)


  Mrv1652309092214382D          

 16 16  0  0  1  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  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
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091   -1.6626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0264   -2.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1758   -0.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
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3D MOL for NP0284771 ((5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one)

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3D SDF for NP0284771 ((5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one)

  Mrv1652309092214382D          

 16 16  0  0  1  0            999 V2000
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  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
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6145   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3091   -1.6626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0264   -2.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1758   -0.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0284771

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)CC1=C\C(OC1=O)=C\[C@@H](O)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O5/c1-6(12)3-8-4-9(16-11(8)15)5-10(14)7(2)13/h4-7,10,12-14H,3H2,1-2H3/b9-5-/t6-,7-,10-/m1/s1

> <INCHI_KEY>
BMCSEOVSJWNEJA-VNVWBWAJSA-N

> <FORMULA>
C11H16O5

> <MOLECULAR_WEIGHT>
228.244

> <EXACT_MASS>
228.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.799659559372266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z)-5-[(2R,3R)-2,3-dihydroxybutylidene]-3-[(2R)-2-hydroxypropyl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
-0.531059106333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.175172534113376

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.640291170481792

> <JCHEM_PKA_STRONGEST_BASIC>
-2.544208468474248

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
59.14520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-5-[(2R,3R)-2,3-dihydroxybutylidene]-3-[(2R)-2-hydroxypropyl]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0284771 ((5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one)
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PDB for NP0284771 ((5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.109  -2.943   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.014  -4.188   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.577  -3.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.049  -4.510   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.328  -1.858   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7   15                                                       
CONECT   15   14    5   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0284771 ((5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one)
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SMILES for NP0284771 ((5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one)
C[C@@H](O)CC1=C\C(OC1=O)=C\[C@@H](O)[C@@H](C)O
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INCHI for NP0284771 ((5z)-5-[(2r,3r)-2,3-dihydroxybutylidene]-3-[(2r)-2-hydroxypropyl]furan-2-one)
InChI=1S/C11H16O5/c1-6(12)3-8-4-9(16-11(8)15)5-10(14)7(2)13/h4-7,10,12-14H,3H2,1-2H3/b9-5-/t6-,7-,10-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H16O5
Average Mass228.2440 Da
Monoisotopic Mass228.09977 Da
IUPAC Name(5Z)-5-[(2R,3R)-2,3-dihydroxybutylidene]-3-[(2R)-2-hydroxypropyl]-2,5-dihydrofuran-2-one
Traditional Name(5Z)-5-[(2R,3R)-2,3-dihydroxybutylidene]-3-[(2R)-2-hydroxypropyl]furan-2-one
CAS Registry NumberNot Available
SMILES
C[C@@H](O)CC1=C\C(OC1=O)=C\[C@@H](O)[C@@H](C)O
InChI Identifier
InChI=1S/C11H16O5/c1-6(12)3-8-4-9(16-11(8)15)5-10(14)7(2)13/h4-7,10,12-14H,3H2,1-2H3/b9-5-/t6-,7-,10-/m1/s1
InChI KeyBMCSEOVSJWNEJA-VNVWBWAJSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • Enol ester
    • 

  • Secondary alcohol
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • 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-0.53ChemAxon
pKa (Strongest Acidic)13.64ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.15 m³·mol⁻¹ChemAxon
Polarizability23.8 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163017781  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]