NP-MRD: Showing NP-Card for (r)-citronellol acetate (NP0172862)

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Record Information

Version

2.0

Created at

2022-09-03 09:53:06 UTC

Updated at

2022-09-03 09:53:06 UTC

NP-MRD ID

NP0172862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(r)-citronellol acetate

Description

Citronellyl acetate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl acetate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Citronellyl acetate is a dust and rose tasting compound. Outside of the human body, Citronellyl acetate has been detected, but not quantified in, celery stalks. (r)-citronellol acetate is found in Citrus sinensis and Leptospermum scoparium. This could make citronellyl acetate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
    5.3369    1.3242   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3391    0.5703   -1.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261    0.3900   -2.2634 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2016    0.0559   -0.4478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -0.6641   -1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1199   -1.0690   -0.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565    0.1047    0.4561 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4879    0.9089    1.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5703   -0.3653    1.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6644   -1.1847    0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3408   -0.3575   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6414   -0.0928   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -0.6396    0.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3144    0.7400   -1.1864 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7003    2.2024   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8451    1.7941    0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    0.6732    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.0904   -1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -1.6205   -1.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4893   -1.7869    0.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3665   -1.6211   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0085    0.7573   -0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9397    1.4259    2.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8928    1.6858    0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2445    0.2425    1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0075    0.5226    1.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375   -0.9744    2.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3890   -1.4825    1.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2812   -2.0894    0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7594    0.0393   -1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4790   -0.3483    0.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3452   -1.7469    1.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349   -0.1483    1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    1.7543   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476    0.8244   -2.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2907    0.2658   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  7 22  1  6
  6 20  1  0
  6 21  1  0
  5 18  1  0
  5 19  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8679.6588679.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8680.9948678.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8682.3268679.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8683.6628678.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8684.9948679.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8686.3298678.522   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8684.9948680.831   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8678.3248678.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8676.9898679.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8675.6558678.522   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8674.3208679.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8672.9868678.522   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8674.3208680.831   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8679.6588680.831   0.000  0.00  0.00           C+0
CONECT    1    2    8   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
Citronellyl acetic acid	Generator
(+)-beta-Citronellol acetate	HMDB
(+)-R-Citronellol acetate	HMDB
(R)-(+)-beta-Citronellol acetate	HMDB
(R)-3,7-Dimethyloct-6-enyl acetate	HMDB
3,7-Dimethyl-acetate(R)-6-octen-1-ol	HMDB
R)-(+)-Citronellol acetate	PhytoBank
(R)-(+)-Citronellyl acetate	PhytoBank
(R)-Citronellol acetate	PhytoBank
(±)-Citronellyl acetate	PhytoBank
1-Acetoxy-3,7-dimethyloct-6-ene	PhytoBank
3,7-Dimethyl-6-octen-1-yl acetate	PhytoBank
8-Acetoxy-2,6-dimethyl-2-octene	PhytoBank
Cephrol acetate	PhytoBank
Citronellyl acetate	PhytoBank
dl-Citronellol acetate	PhytoBank
beta-Citronellol acetate	PhytoBank
β-Citronellol acetate	PhytoBank
beta-Citronellyl acetate	PhytoBank
β-Citronellyl acetate	PhytoBank

Chemical Formula

C₁₂H₂₂O₂

Average Mass

198.3019 Da

Monoisotopic Mass

198.16198 Da

IUPAC Name

(3R)-3,7-dimethyloct-6-en-1-yl acetate

Traditional Name

(3R)-3,7-dimethyloct-6-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H](CCOC(C)=O)CCC=C(C)C

InChI Identifier

InChI=1S/C12H22O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,11H,5,7-9H2,1-4H3/t11-/m1/s1

InChI Key

JOZKFWLRHCDGJA-LLVKDONJSA-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
Citrus sinensis	LOTUS Database	35616633
Leptospermum scoparium	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
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	4.13	ALOGPS
logP	3.19	ChemAxon
logS	-3.5	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	7	ChemAxon
Refractivity	59.64 m³·mol⁻¹	ChemAxon
Polarizability	24.41 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

HMDB0034844

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013410

KNApSAcK ID

Not Available

Chemspider ID

5140836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6708682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (r)-citronellol acetate (NP0172862)

MOL for NP0172862 ((r)-citronellol acetate)

3D MOL for NP0172862 ((r)-citronellol acetate)

3D SDF for NP0172862 ((r)-citronellol acetate)

3D-SDF for NP0172862 ((r)-citronellol acetate)

PDB for NP0172862 ((r)-citronellol acetate)

3D PDB for NP0172862 ((r)-citronellol acetate)

SMILES for NP0172862 ((r)-citronellol acetate)

INCHI for NP0172862 ((r)-citronellol acetate)

Structure for NP0172862 ((r)-citronellol acetate)

3D Structure for NP0172862 ((r)-citronellol acetate)