NP-MRD: Showing NP-Card for 5-dodecyloxolan-2-one (NP0216609)

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Record Information

Version

2.0

Created at

2022-09-05 16:38:47 UTC

Updated at

2022-09-05 16:38:47 UTC

NP-MRD ID

NP0216609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-dodecyloxolan-2-one

Description

5-Dodecyldihydro-2(3H)-furanone, also known as 4-dodecyl-g-butyrolactone or 4-hexadecanolide, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 5-Dodecyldihydro-2(3H)-furanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Dodecyldihydro-2(3H)-furanone has been detected, but not quantified in, a few different foods, such as fruits, parsnips, and root vegetables. This could make 5-dodecyldihydro-2(3H)-furanone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 48  0  0  0  0  0  0  0  0999 V2000
    6.5570   -0.3273    0.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8644   -1.3897   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7769   -0.7242   -1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -0.0866   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7183    0.5715   -0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6933    1.2377   -0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0360    0.2297    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3419   -0.8466    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7309   -0.3235   -0.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8210    0.4090   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8195    0.8699   -1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9802    1.6232   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418    0.9127    0.4824 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4681   -0.3488   -0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9714   -1.0058    1.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8050   -0.7166    2.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4256   -1.3965    3.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2229    0.4585    1.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4412    0.6738    0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6484   -0.5480    0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0825   -0.2757    1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4067   -2.1734    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5743   -1.8412   -0.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716    0.0764   -1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1842   -1.4217   -1.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3134   -0.9056    0.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2884    0.6391    0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678   -0.1741   -1.5569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1611    1.3562   -1.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937    2.0232    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9038    1.7484   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670    0.7613    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550   -0.2135    1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0494   -1.4265   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545   -1.6084    0.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2763    0.3627   -1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364   -1.1863   -1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4484    1.2822    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2403   -0.3143    0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2515    1.5910   -1.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005    0.0383   -1.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5682    2.5257    0.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6001    2.0002   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7049    1.5887    0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2773   -0.1622   -0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6745   -1.0270   -0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8401   -0.4527    1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1320   -2.0831    1.0813 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
  4  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  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  1
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
M  END


  Mrv0541 05061305452D          

 18 18  0  0  0  0            999 V2000
   -8.4875    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7730    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0585    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3441    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6296    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9151    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2007    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    2.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794    0.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3919    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2124    1.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8398    1.9798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 15  1  0  0  0  0
 18 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0216609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCC1CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-15-13-14-16(17)18-15/h15H,2-14H2,1H3

> <INCHI_KEY>
SRIFJCOBFTWCTM-UHFFFAOYSA-N

> <FORMULA>
C16H30O2

> <MOLECULAR_WEIGHT>
254.4082

> <EXACT_MASS>
254.224580204

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
33.094813054315935

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-dodecyloxolan-2-one

> <ALOGPS_LOGP>
6.39

> <JCHEM_LOGP>
5.534335375333333

> <ALOGPS_LOGS>
-6.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.042552424468885

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
75.26089999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.30e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-dodecyloxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0     -15.843   3.069   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -14.510   3.839   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.176   3.069   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.842   3.839   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.509   3.069   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.175   3.839   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.841   3.069   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.508   3.839   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.174   3.069   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.840   3.839   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.507   3.069   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.173   3.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.322   1.538   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.828   1.217   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.161   3.069   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.598   2.551   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.130   2.712   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.568   3.696   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   15                                                       
CONECT   13   14   15                                                       
CONECT   14   13   16                                                       
CONECT   15   12   13   18                                                  
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
2(3H)-Furanone, 5-dodecyldihydro- (9ci)	HMDB
4-Dodecyl-g-butyrolactone	HMDB
4-Hexadecanolide	HMDB
g-Palmitolactone	HMDB
gamma-Hydroxypalmitic acid lactone	HMDB
gamma-Palmitolactone	HMDB
Hexadeca-1,4-lactone	HMDB
Hexadecanoic acid, 4-hydroxy-, gamma-lactone (8ci)	HMDB
Hexadecanoic acid, 4-hydroxy-, laquo gammaraquo -lactone	HMDB
Laquo gammaraquo -hexadecalactone	HMDB
Laquo gammaraquo -palmitolactone	HMDB
Palmito-laquo gammaraquo -lactone	HMDB
4-Dodecyl-γ-butyrolactone	Generator

Chemical Formula

C₁₆H₃₀O₂

Average Mass

254.4082 Da

Monoisotopic Mass

254.22458 Da

IUPAC Name

5-dodecyloxolan-2-one

Traditional Name

5-dodecyloxolan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCC1CCC(=O)O1

InChI Identifier

InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-15-13-14-16(17)18-15/h15H,2-14H2,1H3

InChI Key

SRIFJCOBFTWCTM-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
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 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
logP	6.39	ALOGPS
logP	5.53	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	75.26 m³·mol⁻¹	ChemAxon
Polarizability	33.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031145

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003157

KNApSAcK ID

Not Available

Chemspider ID

88223

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97747

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-dodecyloxolan-2-one (NP0216609)

MOL for NP0216609 (5-dodecyloxolan-2-one)

3D MOL for NP0216609 (5-dodecyloxolan-2-one)

3D SDF for NP0216609 (5-dodecyloxolan-2-one)

3D-SDF for NP0216609 (5-dodecyloxolan-2-one)

PDB for NP0216609 (5-dodecyloxolan-2-one)

3D PDB for NP0216609 (5-dodecyloxolan-2-one)

SMILES for NP0216609 (5-dodecyloxolan-2-one)

INCHI for NP0216609 (5-dodecyloxolan-2-one)

Structure for NP0216609 (5-dodecyloxolan-2-one)

3D Structure for NP0216609 (5-dodecyloxolan-2-one)