NP-MRD: Showing NP-Card for citronellyl isobutyrate (NP0232383)

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Record Information

Version

2.0

Created at

2022-09-06 13:36:20 UTC

Updated at

2022-09-06 13:36:20 UTC

NP-MRD ID

NP0232383

Secondary Accession Numbers

None

Natural Product Identification

Common Name

citronellyl isobutyrate

Description

Citronellyl isobutyrate, also known as fema 2313, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl isobutyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Citronellyl isobutyrate is a sweet, floral, and fruity tasting compound. Outside of the human body, Citronellyl isobutyrate has been detected, but not quantified in, herbs and spices. This could make citronellyl isobutyrate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
   -4.8029   -0.8346   -0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4619    0.5920   -0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4861    1.6315   -0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2471    0.9386    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2087   -0.1195    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161    0.0895   -0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0176   -0.9616   -0.2535 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5591   -2.3595   -0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706   -0.8728    1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1339    0.4712    1.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1683    0.7850    0.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3238    0.0737    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154   -0.9483    1.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573    0.4777   -0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5380   -0.4459   -0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7205    1.9080   -0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0743   -1.2863   -1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6494   -1.3879    0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8263   -0.9154   -0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2354    2.1002   -1.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4936    1.1837   -0.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4222    2.3812    0.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9514    1.9680    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6252   -1.1173    0.3095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8375    0.0994    1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6687    1.1255   -0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3896    0.0394   -1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8457   -0.8562   -0.9963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507   -3.0320   -0.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671   -2.3351   -1.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -2.7915    0.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3244   -1.6892    1.3337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496   -1.0803    1.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3519    1.2416    1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4957    0.5753    2.4651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9352    0.4556   -1.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4029    0.1177   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8084   -0.8120    0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3387   -1.2773   -1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0807    2.3993   -1.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7898    2.4523   -0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4962    2.0163    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  7 28  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
  6 26  1  0
  6 27  1  0
  5 24  1  0
  5 25  1  0
  4 23  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
M  END


  Mrv0541 05061309392D          

 16 15  0  0  0  0            999 V2000
   -5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6184    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232383

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCOC(=O)C(C)C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O2/c1-11(2)7-6-8-13(5)9-10-16-14(15)12(3)4/h7,12-13H,6,8-10H2,1-5H3

> <INCHI_KEY>
ZGPPERKMXSGYRK-UHFFFAOYSA-N

> <FORMULA>
C14H26O2

> <MOLECULAR_WEIGHT>
226.355

> <EXACT_MASS>
226.193280076

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.353838863953712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyloct-6-en-1-yl 2-methylpropanoate

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
4.436702852999998

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.065525336092086

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
68.839

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyloct-6-en-1-yl 2-methylpropanoate

> <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      -9.955   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.621   4.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.716   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.382   1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.286   4.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.954   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.287   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.620   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.953   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.619   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.621   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.382   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.286   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.048   3.437   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.048   4.977   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.715   2.667   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6    7    8                                                       
CONECT    7    6   11                                                       
CONECT    8    6   13                                                       
CONECT    9   10   13                                                       
CONECT   10    9   16                                                       
CONECT   11    1    2    7                                                  
CONECT   12    3    4   14                                                  
CONECT   13    5    8    9                                                  
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
Citronellyl isobutyric acid	Generator
3,7-Dimethyl-6-octen-1-yl 2-methylpropanoate	HMDB
3,7-Dimethyl-6-octen-1-yl isobutyrate	HMDB
3,7-Dimethyl-6-octenyl 2-methylpropanoate	HMDB
3,7-Dimethyl-6-octenyl isobutyrate	HMDB
3,7-Dimethyl-6-octenyl methylpropionate	HMDB
3,7-Dimethyloct-6-enyl isobutyrate	HMDB
Citronellyl 2-methylpropanoate	HMDB
Citronellyl isobutanoate	HMDB
FEMA 2313	HMDB
Isobutyric acid, 3,7-dimethyl-6-octenyl ester	HMDB
Isobutyric acid, 3,7-dimethyl-6-octenyl ester (8ci)	HMDB
Propanoic acid, 2-methyl-, 3,7-dimethyl-6-octen-1-yl ester	HMDB
Propanoic acid, 2-methyl-, 3,7-dimethyl-6-octenyl	HMDB
Propanoic acid, 2-methyl-, 3,7-dimethyl-6-octenyl ester	HMDB

Chemical Formula

C₁₄H₂₆O₂

Average Mass

226.3550 Da

Monoisotopic Mass

226.19328 Da

IUPAC Name

3,7-dimethyloct-6-en-1-yl 2-methylpropanoate

Traditional Name

3,7-dimethyloct-6-en-1-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(CCOC(=O)C(C)C)CCC=C(C)C

InChI Identifier

InChI=1S/C14H26O2/c1-11(2)7-6-8-13(5)9-10-16-14(15)12(3)4/h7,12-13H,6,8-10H2,1-5H3

InChI Key

ZGPPERKMXSGYRK-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 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
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	4.86	ALOGPS
logP	4.44	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-7.1	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	8	ChemAxon
Refractivity	68.84 m³·mol⁻¹	ChemAxon
Polarizability	28.35 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

HMDB0037228

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016235

KNApSAcK ID

Not Available

Chemspider ID

54946

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60985

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for citronellyl isobutyrate (NP0232383)

MOL for NP0232383 (citronellyl isobutyrate)

3D MOL for NP0232383 (citronellyl isobutyrate)

3D SDF for NP0232383 (citronellyl isobutyrate)

3D-SDF for NP0232383 (citronellyl isobutyrate)

PDB for NP0232383 (citronellyl isobutyrate)

3D PDB for NP0232383 (citronellyl isobutyrate)

SMILES for NP0232383 (citronellyl isobutyrate)

INCHI for NP0232383 (citronellyl isobutyrate)

Structure for NP0232383 (citronellyl isobutyrate)

3D Structure for NP0232383 (citronellyl isobutyrate)