NP-MRD: Showing NP-Card for (E)-2-Undecenal (NP0070678)

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Record Information

Version

2.0

Created at

2022-04-28 16:08:24 UTC

Updated at

2022-04-28 16:08:24 UTC

NP-MRD ID

NP0070678

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(E)-2-Undecenal

Description

2-Undecenal, also known as (2E)-2-undecenal or trans-2-undecenal, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, 2-undecenal is considered to be a fatty aldehyde lipid molecule. 2-Undecenal is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Undecenal is a citrus, fat, and fresh tasting compound. Outside of the human body, 2-Undecenal has been detected, but not quantified in, several different foods, such as citrus, fishes, herbs and spices, nuts, and milk and milk products. This could make 2-undecenal a potential biomarker for the consumption of these foods. (E)-2-Undecenal is found in Ailanthus altissima, Anthemis aciphylla and Anthemis aciphylla BOISS.var.discoidea BOISS. (E)-2-Undecenal was first documented in 2003 (PMID: 12848511). A 2-undecenal in which the C=C bond has E configuration (PMID: 25340465) (PMID: 20164502) (PMID: 22224661) (PMID: 24601090).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 31  0  0  0  0  0  0  0  0999 V2000
   -4.3489    1.0509    1.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1226    0.8662   -0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1149   -0.2106   -0.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048    0.1748    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379   -0.8750   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298   -0.4174    0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.4683    0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9070   -1.0884    0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4469    0.1790    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6370    0.1933   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1968    1.4224   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3153    1.4240   -1.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4248    1.2179    1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9716    0.1370    1.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7884    1.9038    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7780    1.8520   -0.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0844    0.6297   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5046   -1.1596   -0.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034   -0.3030   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5090    1.1670   -0.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    0.2954    1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6230   -1.1240   -1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0809   -1.7860    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350    0.5907    0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290   -0.4272    1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219   -1.6591   -0.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -2.3990    0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7772   -1.0168    1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198   -1.9028    0.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970    1.1196    0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048   -0.7193   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    2.3329   -0.6323 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  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
M  END

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       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.933   4.771   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.933   6.311   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol

Synonyms

Value	Source
(2E)-2-Undecenal	ChEBI
(e)-Undec-2-enal	ChEBI
trans-2-Undecenal	ChEBI
trans-Undec-2-enal	ChEBI
FEMA 3423	HMDB
trans-2-Undecen-1-al	HMDB
(2E)-Undecenal	HMDB
Undecenal	HMDB
2-Undecenal	ChEBI

Chemical Formula

C₁₁H₂₀O

Average Mass

168.2759 Da

Monoisotopic Mass

168.15142 Da

IUPAC Name

(2E)-undec-2-enal

Traditional Name

(2E)-undec-2-enal

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C\C=O

InChI Identifier

InChI=1S/C11H20O/c1-2-3-4-5-6-7-8-9-10-11-12/h9-11H,2-8H2,1H3/b10-9+

InChI Key

PANBRUWVURLWGY-MDZDMXLPSA-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
Ailanthus altissima	LOTUS Database	35616633
Anthemis aciphylla	LOTUS Database	35616633
Anthemis aciphylla BOISS.var.discoidea BOISS	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents

Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Fatty aldehydes (LMFA06000065 )

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	4.93	ALOGPS
logP	3.87	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.2	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	8	ChemAxon
Refractivity	54.25 m³·mol⁻¹	ChemAxon
Polarizability	22.16 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

HMDB0040247

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019963

KNApSAcK ID

Not Available

Chemspider ID

4446477

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283356

PDB ID

Not Available

ChEBI ID

132843

Good Scents ID

Not Available

References

General References

Donega MA, Mello SC, Moraes RM, Jain SK, Tekwani BL, Cantrell CL: Pharmacological activities of cilantro's aliphatic aldehydes against Leishmania donovani. Planta Med. 2014 Dec;80(18):1706-11. doi: 10.1055/s-0034-1383183. Epub 2014 Oct 23. [PubMed:25340465 ]
Sjaastad AK, Jorgensen RB, Svendsen K: Exposure to polycyclic aromatic hydrocarbons (PAHs), mutagenic aldehydes and particulate matter during pan frying of beefsteak. Occup Environ Med. 2010 Apr;67(4):228-32. doi: 10.1136/oem.2009.046144. Epub 2010 Feb 17. [PubMed:20164502 ]
Lin J, Blank I: Odorants generated by thermally induced degradation of phospholipids. J Agric Food Chem. 2003 Jul 16;51(15):4364-9. doi: 10.1021/jf034300m. [PubMed:12848511 ]
Caboni P, Ntalli NG, Aissani N, Cavoski I, Angioni A: Nematicidal activity of (E,E)-2,4-decadienal and (E)-2-decenal from Ailanthus altissima against Meloidogyne javanica. J Agric Food Chem. 2012 Feb 1;60(4):1146-51. doi: 10.1021/jf2044586. Epub 2012 Jan 19. [PubMed:22224661 ]
Aldrich JR, Chauhan KR, Zhang A, Zarbin PH: Exocrine secretions of wheel bugs (Heteroptera: Reduviidae: Arilus spp.): clarification and chemistry. Z Naturforsch C J Biosci. 2013 Nov-Dec;68(11-12):522-6. [PubMed:24601090 ]

Showing NP-Card for (E)-2-Undecenal (NP0070678)

MOL for NP0070678 ((E)-2-Undecenal)

3D MOL for NP0070678 ((E)-2-Undecenal)

3D SDF for NP0070678 ((E)-2-Undecenal)

3D-SDF for NP0070678 ((E)-2-Undecenal)

PDB for NP0070678 ((E)-2-Undecenal)

3D PDB for NP0070678 ((E)-2-Undecenal)

SMILES for NP0070678 ((E)-2-Undecenal)

INCHI for NP0070678 ((E)-2-Undecenal)

Structure for NP0070678 ((E)-2-Undecenal)

3D Structure for NP0070678 ((E)-2-Undecenal)