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Showing NP-Card for (5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one (NP0326973)

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Record Information
Version1.0
Created at2022-09-12 09:05:44 UTC
Updated at2022-09-12 09:05:45 UTC
NP-MRD IDNP0326973
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one
Description(5S,S)-5-methyl-3-(6-methyloctyl)furan-2(5H)-one belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. (5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one is found in Streptomyces avermitilis. Based on a literature review very few articles have been published on (5S,S)-5-methyl-3-(6-methyloctyl)furan-2(5H)-one.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0326973 ((5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one)


  Mrv1652309122211052D          

 16 16  0  0  1  0            999 V2000
    3.5108   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9398   -4.3205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9398   -5.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0832   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2266   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9803   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5323   -4.5980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3528   -4.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1198   -5.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3128   -5.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6997   -5.6930    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  1  0  0  0
  3  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
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3D MOL for NP0326973 ((5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one)

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3D SDF for NP0326973 ((5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one)

  Mrv1652309122211052D          

 16 16  0  0  1  0            999 V2000
    3.5108   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9398   -4.3205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9398   -5.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0832   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5121   -3.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2266   -4.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9803   -3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5323   -4.5980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3528   -4.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1198   -5.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3128   -5.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6997   -5.6930    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  1  0  0  0
  3  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0326973

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)CCCCCC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-4-11(2)8-6-5-7-9-13-10-12(3)16-14(13)15/h10-12H,4-9H2,1-3H3/t11-,12-/m0/s1

> <INCHI_KEY>
DIGSICVZYKFCTI-RYUDHWBXSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.344

> <EXACT_MASS>
224.177630013

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.568172128890897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-5-methyl-3-[(6S)-6-methyloctyl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
4.747740854

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.470827754848901

> <JCHEM_PKA_STRONGEST_BASIC>
-6.879887748932981

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
66.77890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-methyl-3-[(6S)-6-methyloctyl]-5H-furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0326973 ((5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one)
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PDB for NP0326973 ((5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-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  C   UNK     0       6.554  -8.065   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.887  -7.295   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.221  -8.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.221  -9.605   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.555  -7.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.888  -8.065   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.222  -7.295   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.556  -8.065   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.889  -7.295   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.223  -8.065   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.630  -7.439   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.660  -8.583   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.192  -8.422   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.890  -9.917   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      17.384  -9.597   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.239 -10.627   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   10   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 NP0326973 ((5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one)
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SMILES for NP0326973 ((5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one)
CC[C@H](C)CCCCCC1=C[C@H](C)OC1=O
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INCHI for NP0326973 ((5s)-5-methyl-3-[(6s)-6-methyloctyl]-5h-furan-2-one)
InChI=1S/C14H24O2/c1-4-11(2)8-6-5-7-9-13-10-12(3)16-14(13)15/h10-12H,4-9H2,1-3H3/t11-,12-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC14H24O2
Average Mass224.3440 Da
Monoisotopic Mass224.17763 Da
IUPAC Name(5S)-5-methyl-3-[(6S)-6-methyloctyl]-2,5-dihydrofuran-2-one
Traditional Name(5S)-5-methyl-3-[(6S)-6-methyloctyl]-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
CC[C@H](C)CCCCCC1=C[C@H](C)OC1=O
InChI Identifier
InChI=1S/C14H24O2/c1-4-11(2)8-6-5-7-9-13-10-12(3)16-14(13)15/h10-12H,4-9H2,1-3H3/t11-,12-/m0/s1
InChI KeyDIGSICVZYKFCTI-RYUDHWBXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces avermitilisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty alcohols  
Direct ParentAnnonaceous acetogenins  
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
    • 

  • 2-furanone
    • 

  • Dihydrofuran
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen 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
logP4.75ChemAxon
pKa (Strongest Acidic)13.47ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity66.78 m³·mol⁻¹ChemAxon
Polarizability27.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID17248843  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16090230  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]