Showing NP-Card for 5-Dodecanolide (NP0048882)

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Record Information
Version2.0
Created at2022-03-17 21:03:41 UTC
Updated at2022-03-17 21:03:41 UTC
NP-MRD IDNP0048882
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Dodecanolide
DescriptionXi-5-Dodecanolide, also known as 5-dodecalactone or dodecan-5-olide, belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Thus, XI-5-dodecanolide is considered to be a fatty ester lipid molecule. Xi-5-Dodecanolide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Xi-5-Dodecanolide is a sweet, buttery, and coconut tasting compound. Outside of the human body, xi-5-Dodecanolide is found, on average, in the highest concentration within peppermints. Xi-5-Dodecanolide has also been detected, but not quantified in, coconuts and evergreen blackberries. This could make XI-5-dodecanolide a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048882 (5-Dodecanolide)

  Mrv0541 02241208152D          

 14 14  0  0  0  0            999 V2000
   -2.4985    1.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132   -0.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985   -1.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -0.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    0.0014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 14  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
  6 14  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
M  END
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3D MOL for NP0048882 (5-Dodecanolide)

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3D SDF for NP0048882 (5-Dodecanolide)
  Mrv0541 02241208152D          

 14 14  0  0  0  0            999 V2000
   -2.4985    1.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2132   -0.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4985   -1.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -0.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7853   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132   -1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853    0.0014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 14  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
  6 14  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
M  END
> <DATABASE_ID>
NP0048882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC1CCCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h11H,2-10H2,1H3

> <INCHI_KEY>
QRPLZGZHJABGRS-UHFFFAOYSA-N

> <FORMULA>
C12H22O2

> <MOLECULAR_WEIGHT>
198.3019

> <EXACT_MASS>
198.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
24.5851839887846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-heptyloxan-2-one

> <ALOGPS_LOGP>
4.34

> <JCHEM_LOGP>
3.756060715333333

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.041514923717076

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
56.856899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
delta-dodecalactone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048882 (5-Dodecanolide)
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PDB for NP0048882 (5-Dodecanolide)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -4.664   2.309   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.664   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.998   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.998  -1.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.664  -2.306   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.333  -1.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.998  -2.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.667  -1.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.667  -2.309   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.001  -1.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.333  -2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.666  -1.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.998  -2.309   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.333   0.003   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
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                                                            
CONECT   14    2    6                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0048882 (5-Dodecanolide)
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SMILES for NP0048882 (5-Dodecanolide)
CCCCCCCC1CCCC(=O)O1
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INCHI for NP0048882 (5-Dodecanolide)
InChI=1S/C12H22O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h11H,2-10H2,1H3
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View in JSmol
Synonyms
ValueSource
(+/-)-5-dodecanolideHMDB
(+/-)-6-heptyltetrahydro-2H-pyran-2-oneHMDB
(+/-)-delta-heptyl-delta-valerolactoneHMDB
5-DodecalactoneHMDB
5-Hydroxydodecanoic acid delta-lactoneHMDB
5-Hydroxydodecanoic acid lactoneHMDB
6-Heptyltetrahydro-2H-pyran-2-oneHMDB
delta-DodecalactoneHMDB
delta-DodecanolactoneHMDB
delta-Heptyl-delta-valerolactoneHMDB
Dodecan-5-olideHMDB
Dodecanoic acid, 5-hydroxy-, delta-lactoneHMDB
Dodecanolide-1,5HMDB
N-Heptyl-delta-valerolactoneHMDB
Δ-dodecalactoneGenerator
Chemical FormulaC12H22O2
Average Mass198.3019 Da
Monoisotopic Mass198.16198 Da
IUPAC Name6-heptyloxan-2-one
Traditional Namedelta-dodecalactone
CAS Registry Number3051-22-7
SMILES
CCCCCCCC1CCCC(=O)O1
InChI Identifier
InChI=1S/C12H22O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h11H,2-10H2,1H3
InChI KeyQRPLZGZHJABGRS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cocos nuciferaFooDB
Mentha x piperitaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassDelta valerolactones  
Direct ParentDelta valerolactones  
Alternative Parents
Substituents
  • Delta_valerolactone
    • 

  • Delta valerolactone
    • 

  • Oxane
    • 

  • 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 Descriptors
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
logP4.34ALOGPS
logP3.76ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.86 m³·mol⁻¹ChemAxon
Polarizability24.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037742  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016873  
KNApSAcK IDNot Available
Chemspider ID12314  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12844  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available