NP-MRD: Showing NP-Card for (s)-(-)-citronellal (NP0253931)

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Record Information

Version

2.0

Created at

2022-09-07 17:57:02 UTC

Updated at

2022-09-07 17:57:02 UTC

NP-MRD ID

NP0253931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(s)-(-)-citronellal

Description

(S)-Citronellal belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. (s)-(-)-citronellal is found in Citrus hystrix and Melissa officinalis. Thus, (S)-citronellal is considered to be an isoprenoid lipid molecule (S)-Citronellal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.0238    0.3097    0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8024   -0.1983   -0.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9402   -0.7668   -1.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5843   -0.1293   -1.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4578    0.4372   -0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6655   -0.5642   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488    0.1266    0.4193 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2918    1.3366   -0.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8712   -0.8257    0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8746   -0.1527    1.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8826   -0.7757    1.9290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0508    0.0693    0.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8408    1.4117    0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440   -0.2175    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3605   -0.0335   -2.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6609   -1.6798   -2.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7518   -1.0402   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4324   -0.5048   -2.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817    0.7915    0.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    1.3109   -1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2754   -1.3979    0.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -0.8975   -1.3301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3508    0.4891    1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7370    2.2496   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362    1.2189   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    1.4652   -0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3789   -1.1680   -0.2102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5320   -1.7287    1.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325    0.8644    1.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  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
  7  9  1  0
  9 10  1  0
 10 11  2  0
  7 23  1  1
  8 24  1  0
  8 25  1  0
  8 26  1  0
  6 21  1  0
  6 22  1  0
  5 19  1  0
  5 20  1  0
  4 18  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
M  END

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0      -4.977   4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.310   4.414   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.357  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.976   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.691   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.025   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.644   3.644   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.357   1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.358   2.104   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      -0.976   0.564   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    6                                                       
CONECT    5    4    9                                                       
CONECT    6    4   10                                                       
CONECT    7    8   10                                                       
CONECT    8    7   11                                                       
CONECT    9    1    2    5                                                  
CONECT   10    3    6    7   12                                             
CONECT   11    8                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol

Synonyms

Value	Source
(3S)-(-)-Citronellal	ChEBI
(3S)-3,7-Dimethyl-6-octenal	ChEBI
(S)-3,7-Dimethyl-6-octenal	ChEBI
(S)-3,7-Dimethyloct-6-enal	ChEBI

Chemical Formula

C₁₀H₁₈O

Average Mass

154.2530 Da

Monoisotopic Mass

154.13577 Da

IUPAC Name

(3S)-3,7-dimethyloct-6-enal

Traditional Name

(S)-(-)-citronellal

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m0/s1

InChI Key

NEHNMFOYXAPHSD-JTQLQIEISA-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 hystrix	LOTUS Database	35616633
Melissa officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Medium-chain aldehyde
Alpha-hydrogen aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

citronellal (CHEBI:368 )
Acyclic monoterpenoids (C11384 )
Linear monoterpenes (C11384 )
Acyclic monoterpenoids (LMPR0102010011 )

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	2.71	ChemAxon
pKa (Strongest Acidic)	18.32	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	49.3 m³·mol⁻¹	ChemAxon
Polarizability	19.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014618

KNApSAcK ID

C00010309

Chemspider ID

Not Available

KEGG Compound ID

C11384

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443157

PDB ID

Not Available

ChEBI ID

368

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (s)-(-)-citronellal (NP0253931)

MOL for NP0253931 ((s)-(-)-citronellal)

3D MOL for NP0253931 ((s)-(-)-citronellal)

3D SDF for NP0253931 ((s)-(-)-citronellal)

3D-SDF for NP0253931 ((s)-(-)-citronellal)

PDB for NP0253931 ((s)-(-)-citronellal)

3D PDB for NP0253931 ((s)-(-)-citronellal)

SMILES for NP0253931 ((s)-(-)-citronellal)

INCHI for NP0253931 ((s)-(-)-citronellal)

Structure for NP0253931 ((s)-(-)-citronellal)

3D Structure for NP0253931 ((s)-(-)-citronellal)