NP-MRD: Showing NP-Card for hexyl cinnamic aldehyde (NP0255811)

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Record Information

Version

2.0

Created at

2022-09-07 20:26:16 UTC

Updated at

2022-09-07 20:26:16 UTC

NP-MRD ID

NP0255811

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hexyl cinnamic aldehyde

Description

2-Hexyl-3-phenyl-2-propenal, also known as alpha-hexylcinnamic aldehyde or 2-(phenylmethylene)octanal, belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. 2-Hexyl-3-phenyl-2-propenal is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Hexyl-3-phenyl-2-propenal is a floral, fresh, and green tasting compound. hexyl cinnamic aldehyde is found in Plectranthus glabratus. hexyl cinnamic aldehyde was first documented in 2012 (PMID: 22302311). Outside of the human body,.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
    4.5342   -0.0654   -1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6513   -0.2456    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7165    0.9349    0.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.8706    1.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -0.3792    1.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -0.3774   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -1.5886   -0.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1589   -2.9458   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0821   -3.0254   -0.0166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0638   -1.4416   -0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8259   -0.2139   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560    0.7972   -1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4341    1.9284   -0.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3784    2.0429    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5707    1.0466    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7894   -0.0805    0.8610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2055   -0.9420   -1.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0955    0.8868   -1.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8599   -0.0503   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1206   -1.2010   -0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3073   -0.2631    0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1563    0.9655   -0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3024    1.8995    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0947    1.7622    1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3507    0.9499    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927   -1.2633    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2583   -0.4417    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4735    0.5462   -0.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8247   -0.5330   -0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7702   -3.8183   -0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6285   -2.4004   -0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    0.6849   -1.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2740    2.7008   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9870    2.9369    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3209    1.1847    1.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9427   -0.8612    1.5966 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
M  END


  Mrv0541 05061306062D          

 16 16  0  0  0  0            999 V2000
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  6  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0255811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC\C(C=O)=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O/c1-2-3-4-6-11-15(13-16)12-14-9-7-5-8-10-14/h5,7-10,12-13H,2-4,6,11H2,1H3/b15-12+

> <INCHI_KEY>
GUUHFMWKWLOQMM-NTCAYCPXSA-N

> <FORMULA>
C15H20O

> <MOLECULAR_WEIGHT>
216.3187

> <EXACT_MASS>
216.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.347885094617652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-(phenylmethylidene)octanal

> <ALOGPS_LOGP>
4.44

> <JCHEM_LOGP>
4.595863822

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.494007019978051

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
69.4966

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexyl cinnamic aldehyde

> <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      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    7    8                                                       
CONECT    6    4   11                                                       
CONECT    7    5    9                                                       
CONECT    8    5   10                                                       
CONECT    9    7   14                                                       
CONECT   10    8   14                                                       
CONECT   11    6   15                                                       
CONECT   12   14   15                                                       
CONECT   13   15   16                                                       
CONECT   14    9   10   12                                                  
CONECT   15   11   12   13                                                  
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
2-(Phenylmethylene)octanal	ChEBI
2-[(e)-Benzylidene]octanal	ChEBI
2-Benzylideneoctanal	ChEBI
2-Hexylcinnamaldehyde	ChEBI
alpha-Hexyl-beta-phenylacrolein	ChEBI
alpha-Hexylcinnamic aldehyde	ChEBI
alpha-Hexylcinnamyl aldehyde	ChEBI
alpha-N-Hexyl-beta-phenylacrolein	ChEBI
Hexyl cinnamic aldehyde	ChEBI
a-Hexyl-b-phenylacrolein	Generator
Α-hexyl-β-phenylacrolein	Generator
a-Hexylcinnamic aldehyde	Generator
Α-hexylcinnamic aldehyde	Generator
a-Hexylcinnamyl aldehyde	Generator
Α-hexylcinnamyl aldehyde	Generator
a-N-Hexyl-b-phenylacrolein	Generator
Α-N-hexyl-β-phenylacrolein	Generator
(2Z)-2-Hexyl-3-phenyl-2-propenal	HMDB
-Hexyl-3-phenyl-propenal	HMDB
2-(Phenylmethylene)-octanal	HMDB
2-(Phenylmethylene)octanal, 9ci	HMDB
2-Hexenyl cynnamaldehyde	HMDB
2-Hexyl-3-phenyl-propenal	HMDB
3-Phenyl-2-propenal dimethyl acetal	HMDB
a-Hexylcinnamaldehyde, 8ci	HMDB
alpha -Hexylcinnamaldehyde	HMDB
alpha -Hexylcinnamic aldehyde	HMDB
alpha -N-Hexyl-alpha -hexylcinnamaldehyde	HMDB
alpha -N-Hexyl-beta -phenylacrolein	HMDB
Cinnamaldehyde, dimethyl acetal	HMDB
Cinnamic aldehyde dimethyl acetal	HMDB
FEMA 2569	HMDB
Hexylcinnamaldehyde	HMDB
N-Hexyl cinnamaldehyde	HMDB
2-Hexyl-3-phenyl-2-propenal	ChEBI
a-Hexylcinnamaldehyde	Generator
Α-hexylcinnamaldehyde	Generator
Hexyl cinnamal	MeSH
Hexyl cinnamylaldehyde	MeSH

Chemical Formula

C₁₅H₂₀O

Average Mass

216.3187 Da

Monoisotopic Mass

216.15142 Da

IUPAC Name

(2E)-2-(phenylmethylidene)octanal

Traditional Name

hexyl cinnamic aldehyde

CAS Registry Number

Not Available

SMILES

CCCCCC\C(C=O)=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H20O/c1-2-3-4-6-11-15(13-16)12-14-9-7-5-8-10-14/h5,7-10,12-13H,2-4,6,11H2,1H3/b15-12+

InChI Key

GUUHFMWKWLOQMM-NTCAYCPXSA-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
Plectranthus glabratus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamaldehydes

Sub Class

Not Available

Direct Parent

Cinnamaldehydes

Alternative Parents

Substituents

Cinnamaldehyde
Benzenoid
Monocyclic benzene moiety
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cinnamaldehydes (CHEBI:55365 )

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	4.44	ALOGPS
logP	4.6	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-4.5	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	7	ChemAxon
Refractivity	69.5 m³·mol⁻¹	ChemAxon
Polarizability	26.35 Å³	ChemAxon
Number of Rings	1	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

HMDB0031736

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008404

KNApSAcK ID

Not Available

Chemspider ID

1267362

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1550884

PDB ID

Not Available

ChEBI ID

55365

Good Scents ID

Not Available

References

General References

Adenuga D, Woolhiser MR, Gollapudi BB, Boverhof DR: Differential gene expression responses distinguish contact and respiratory sensitizers and nonsensitizing irritants in the local lymph node assay. Toxicol Sci. 2012 Apr;126(2):413-25. doi: 10.1093/toxsci/kfs071. Epub 2012 Feb 2. [PubMed:22302311 ]
LOTUS database [Link]

Showing NP-Card for hexyl cinnamic aldehyde (NP0255811)

MOL for NP0255811 (hexyl cinnamic aldehyde)

3D MOL for NP0255811 (hexyl cinnamic aldehyde)

3D SDF for NP0255811 (hexyl cinnamic aldehyde)

3D-SDF for NP0255811 (hexyl cinnamic aldehyde)

PDB for NP0255811 (hexyl cinnamic aldehyde)

3D PDB for NP0255811 (hexyl cinnamic aldehyde)

SMILES for NP0255811 (hexyl cinnamic aldehyde)

INCHI for NP0255811 (hexyl cinnamic aldehyde)

Structure for NP0255811 (hexyl cinnamic aldehyde)

3D Structure for NP0255811 (hexyl cinnamic aldehyde)