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Showing NP-Card for 5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one (NP0306129)

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Record Information
Version2.0
Created at2022-09-10 22:25:06 UTC
Updated at2022-09-10 22:25:07 UTC
NP-MRD IDNP0306129
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one
DescriptionAkolactone A belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one is found in Lindera glauca and Litsea akoensis. 5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one was first documented in 2003 (PMID: 14730149). Based on a literature review a small amount of articles have been published on Akolactone A (PMID: 22728355) (PMID: 12919047).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0306129 (5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one)


  Mrv1652309112200252D          

 21 21  0  0  0  0            999 V2000
    6.6966   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4110   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1255   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8400   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5544   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2689   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9834   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4123   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1268   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5557   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2702   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9847   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6991   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4528   -6.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0049   -7.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8253   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924   -8.1810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7854   -8.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1723   -8.5615    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  0  0  0  0
  3  4  1  0  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  1  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
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3D MOL for NP0306129 (5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one)

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3D SDF for NP0306129 (5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one)

  Mrv1652309112200252D          

 21 21  0  0  0  0            999 V2000
    6.6966   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4110   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1255   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8400   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5544   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2689   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9834   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4123   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1268   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5557   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2702   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9847   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6991   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4528   -6.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0049   -7.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8253   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924   -8.1810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7854   -8.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1723   -8.5615    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  0  0  0  0
  3  4  1  0  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  1  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0306129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC\C=C\C1=CC(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16-17(2)21-19(18)20/h14-17H,3-13H2,1-2H3/b15-14+

> <INCHI_KEY>
OWNIRRPVQFRFNQ-CCEZHUSRSA-N

> <FORMULA>
C19H32O2

> <MOLECULAR_WEIGHT>
292.463

> <EXACT_MASS>
292.24023027

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.22171469023025

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-3-[(1E)-tetradec-1-en-1-yl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
6.766212091000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.663421379513103

> <JCHEM_PKA_STRONGEST_BASIC>
-6.946682899116453

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
90.9529

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-3-[(1E)-tetradec-1-en-1-yl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0306129 (5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one)
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PDB for NP0306129 (5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      12.500 -13.419   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.834 -12.649   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.168 -13.419   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.501 -12.649   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.835 -13.419   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.169 -12.649   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.502 -13.419   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.836 -12.649   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.170 -13.419   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.503 -12.649   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.837 -13.419   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.171 -12.649   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.504 -13.419   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.838 -12.649   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.172 -13.419   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.579 -12.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.609 -13.937   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.141 -13.776   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      32.839 -15.271   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      31.333 -14.951   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      30.188 -15.981   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

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3D PDB for NP0306129 (5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one)
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SMILES for NP0306129 (5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one)
CCCCCCCCCCCC\C=C\C1=CC(C)OC1=O
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INCHI for NP0306129 (5-methyl-3-[(1e)-tetradec-1-en-1-yl]-5h-furan-2-one)
InChI=1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16-17(2)21-19(18)20/h14-17H,3-13H2,1-2H3/b15-14+
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SynonymsNot Available
Chemical FormulaC19H32O2
Average Mass292.4630 Da
Monoisotopic Mass292.24023 Da
IUPAC Name5-methyl-3-[(1E)-tetradec-1-en-1-yl]-2,5-dihydrofuran-2-one
Traditional Name5-methyl-3-[(1E)-tetradec-1-en-1-yl]-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCC\C=C\C1=CC(C)OC1=O
InChI Identifier
InChI=1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16-17(2)21-19(18)20/h14-17H,3-13H2,1-2H3/b15-14+
InChI KeyOWNIRRPVQFRFNQ-CCEZHUSRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lindera glaucaLOTUS Database
Litsea akoensisLOTUS 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
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP6.77ChemAxon
pKa (Strongest Acidic)13.66ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity90.95 m³·mol⁻¹ChemAxon
Polarizability38.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00042204  
Chemspider ID8261283  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10085746  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yang CP, Huang GJ, Huang HC, Chen YC, Chang CI, Wang SY, Chen IS, Tseng YH, Chien SC, Kuo YH: A new butanolide compound from the aerial part of Lindera akoensis with anti-inflammatory activity. Molecules. 2012 May 31;17(6):6585-92. doi: 10.3390/molecules17066585. [PubMed:22728355  ] 
  2. Makabe H, Okajima M, Konno H, Kamo T, Hirota M: Efficient synthesis of akolactone A via Pd-catalyzed carbonylation. Biosci Biotechnol Biochem. 2003 Dec;67(12):2658-60. doi: 10.1271/bbb.67.2658. [PubMed:14730149  ] 
  3. Gallagher WP, Maleczka RE Jr: PMHS-mediated couplings of alkynes or benzothiazoles with various electrophiles: application to the synthesis of (-)-akolactone A. J Org Chem. 2003 Aug 22;68(17):6775-9. doi: 10.1021/jo034463+. [PubMed:12919047  ] 
  4. LOTUS database [Link]