NP-MRD: Showing NP-Card for Citronellyl pentanoate (NP0084544)

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Record Information

Version

2.0

Created at

2022-04-29 05:15:17 UTC

Updated at

2022-04-29 05:15:17 UTC

NP-MRD ID

NP0084544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citronellyl pentanoate

Description

Citronellyl pentanoate, also known as citronellyl valerate or E469, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl pentanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Citronellyl pentanoate is a herbal, honey, and rose tasting compound. Outside of the human body, Citronellyl pentanoate has been detected, but not quantified in, herbs and spices. Citronellyl pentanoate is found in Boronia citriodora and Curcuma longa. This could make citronellyl pentanoate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 44  0  0  0  0  0  0  0  0999 V2000
    4.2239    2.8127   -1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6295    1.3929   -2.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5643    0.7223   -2.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    0.5664   -2.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2634   -0.2318   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559   -0.7368   -0.5791 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1151   -0.4477   -0.1849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2547   -1.2244    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0676   -1.3788    1.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1169   -2.0232    0.9193 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6564   -3.4338    0.5059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766   -2.1330    1.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101   -0.9710    1.7308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5762   -0.0543    0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3235    1.2225    0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5849    2.1477   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8063    1.7838    1.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0002    3.2412   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0201    3.4531   -2.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031    2.6982   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5143    1.5298   -2.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9133    0.8653   -1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3889    1.3158   -3.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9526   -0.2660   -3.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354    1.5922   -1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5414    0.1345   -2.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -0.6667    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7311   -2.2018    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284   -1.9353    2.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263   -0.3701    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1438   -1.4849   -0.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171   -4.1394    1.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4360   -3.7615   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -3.4109   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0701   -2.7564    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4878   -2.8088    2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0208   -0.3832    2.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -1.3848    2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852   -0.4295   -0.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1887    1.7413   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0324    3.1154   -0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6756    2.3739   -0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7334    2.9103    1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4646    1.5612    2.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7660    1.4536    2.1624 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
M  END

  Mrv0541 05061309392D          

 17 16  0  0  0  0            999 V2000
    0.6336   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9217   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7783   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4927   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  8  2  0  0  0  0
 14  4  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 16 15  2  0  0  0  0
 17 12  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC(=O)OCCC(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H28O2/c1-5-6-10-15(16)17-12-11-14(4)9-7-8-13(2)3/h8,14H,5-7,9-12H2,1-4H3

> <INCHI_KEY>
PFOJEJPZUVQHEH-UHFFFAOYSA-N

> <FORMULA>
C15H28O2

> <MOLECULAR_WEIGHT>
240.3816

> <EXACT_MASS>
240.20893014

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.66155656877291

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyloct-6-en-1-yl pentanoate

> <ALOGPS_LOGP>
5.41

> <JCHEM_LOGP>
4.782853904666666

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.03274614863308

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
73.4665

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyloct-6-en-1-yl pentanoate

> <JCHEM_VEBER_RULE>
1

$$$$

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       1.183  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.521  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.187  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.852  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.519  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.853  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.186  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.518  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.185  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.187  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.852  -1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.517  -1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.517  -2.874   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.851  -0.564   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    1    6                                                       
CONECT    6    5   10                                                       
CONECT    7    8    9                                                       
CONECT    8    7   13                                                       
CONECT    9    7   14                                                       
CONECT   10    6   15                                                       
CONECT   11   12   14                                                       
CONECT   12   11   17                                                       
CONECT   13    2    3    8                                                  
CONECT   14    4    9   11                                                  
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
Citronellyl pentanoic acid	Generator
3,7-Dimethyl-6-octen-1-yl pentanoate	HMDB
3,7-Dimethyl-6-octen-1-yl valerate	HMDB
3,7-Dimethyloct-6-enyl valerate	HMDB
Citronellyl valerate	HMDB
e469	HMDB
FEMA 2317	HMDB
Pentanoic acid, 3,7-dimethyl-6-octen-1-yl ester	HMDB
Pentanoic acid, 3,7-dimethyl-6-octenyl ester	HMDB
Valeric acid, 3,7-dimethyl-6-octen-1-yl ester	HMDB

Chemical Formula

C₁₅H₂₈O₂

Average Mass

240.3816 Da

Monoisotopic Mass

240.20893 Da

IUPAC Name

3,7-dimethyloct-6-en-1-yl pentanoate

Traditional Name

3,7-dimethyloct-6-en-1-yl pentanoate

CAS Registry Number

Not Available

SMILES

CCCCC(=O)OCCC(C)CCC=C(C)C

InChI Identifier

InChI=1S/C15H28O2/c1-5-6-10-15(16)17-12-11-14(4)9-7-8-13(2)3/h8,14H,5-7,9-12H2,1-4H3

InChI Key

PFOJEJPZUVQHEH-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Boronia citriodora	Plant	KNApSAcK
Curcuma longa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Monoterpenoid
Acyclic monoterpenoid
Fatty acid ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	5.41	ALOGPS
logP	4.78	ChemAxon
logS	-4.7	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	10	ChemAxon
Refractivity	73.47 m³·mol⁻¹	ChemAxon
Polarizability	30.66 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037229

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016236

KNApSAcK ID

Not Available

Chemspider ID

55342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61416

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Citronellyl pentanoate (NP0084544)

MOL for NP0084544 (Citronellyl pentanoate)

3D MOL for NP0084544 (Citronellyl pentanoate)

3D SDF for NP0084544 (Citronellyl pentanoate)

3D-SDF for NP0084544 (Citronellyl pentanoate)

PDB for NP0084544 (Citronellyl pentanoate)

3D PDB for NP0084544 (Citronellyl pentanoate)

SMILES for NP0084544 (Citronellyl pentanoate)

INCHI for NP0084544 (Citronellyl pentanoate)

Structure for NP0084544 (Citronellyl pentanoate)

3D Structure for NP0084544 (Citronellyl pentanoate)