NP-MRD: Showing NP-Card for 5-methyl-3-(6-methyloctyl)-5h-furan-2-one (NP0234822)

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Record Information

Version

2.0

Created at

2022-09-06 17:06:21 UTC

Updated at

2022-09-06 17:06:21 UTC

NP-MRD ID

NP0234822

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methyl-3-(6-methyloctyl)-5h-furan-2-one

Description

SCHEMBL17867001 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. 5-methyl-3-(6-methyloctyl)-5h-furan-2-one is found in Streptomyces avermitilis. Based on a literature review very few articles have been published on SCHEMBL17867001.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
   -5.1869    0.1275    1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9845    0.7909    0.6290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489   -0.2644    0.2145 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6145   -1.1656   -0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824    0.5067   -0.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6754   -0.3772   -0.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276    0.5179   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515    1.4760   -0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5205    0.8007    0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -0.0222    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -0.2398   -0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -1.1644   -0.1417 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8327   -0.4744   -0.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4178   -1.4616    1.2117 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3243   -0.7956    1.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -0.7997    2.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3260   -0.9145    0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0779    0.7213    0.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1105    0.1746    2.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5662    1.4990    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2863    1.3905   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -0.8506    1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8586   -2.1704   -0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6219   -0.7766   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0342   -1.2833   -1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061    1.1373    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376    1.1280   -1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0123   -1.0137   -1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2557   -1.0416   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1082    1.1753   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1315   -0.0513   -1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465    2.1464   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572    2.2200   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6864    1.6011    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6976    0.1727    1.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2915    0.1598   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -2.0426   -0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057    0.4381    0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7019   -1.1291   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7727   -0.1453   -1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  1
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 11 36  1  0
 12 37  1  6
 13 38  1  0
 13 39  1  0
 13 40  1  0
M  END


  Mrv1652309062219062D          

 16 16  0  0  0  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  0  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  0  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  0  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  0  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>
NP0234822

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)CCCCCC1=CC(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

> <INCHI_KEY>
DIGSICVZYKFCTI-UHFFFAOYSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.344

> <EXACT_MASS>
224.177630013

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.557162189880025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methyl-3-(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>
66.7789

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₄O₂

Average Mass

224.3440 Da

Monoisotopic Mass

224.17763 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC(C)CCCCCC1=CC(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

InChI Key

DIGSICVZYKFCTI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces avermitilis	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73240312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-methyl-3-(6-methyloctyl)-5h-furan-2-one (NP0234822)

MOL for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

3D MOL for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

3D SDF for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

3D-SDF for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

PDB for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

3D PDB for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

SMILES for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

INCHI for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

Structure for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)

3D Structure for NP0234822 (5-methyl-3-(6-methyloctyl)-5h-furan-2-one)