NP-MRD: Showing NP-Card for (8z,11z,14z)-heptadecatrienal (NP0288420)

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Record Information

Version

2.0

Created at

2022-09-09 18:06:56 UTC

Updated at

2022-09-09 18:06:56 UTC

NP-MRD ID

NP0288420

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8z,11z,14z)-heptadecatrienal

Description

(8Z,11Z,14Z)-heptadecatrienal, also known as norlinolenic aldehyde, belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms. Thus, (8Z,11Z,14Z)-heptadecatrienal is considered to be a fatty aldehyde. (8z,11z,14z)-heptadecatrienal is found in Nicotiana tabacum. (8z,11z,14z)-heptadecatrienal was first documented in 1998 (PMID: 11711065). Based on a literature review a small amount of articles have been published on (8Z,11Z,14Z)-heptadecatrienal (PMID: 30445846) (PMID: 17898513) (PMID: 16041141).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 45  0  0  0  0  0  0  0  0999 V2000
    7.6304    1.1251    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9003   -0.2010    0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239   -0.0549   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9318   -0.1558   -0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9940   -0.4284    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738    0.7266    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7899    0.6885    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1070   -0.6313   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4316   -0.5320   -1.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8625   -0.6863   -1.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7717   -0.9755   -0.3972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8259    0.1323   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869   -0.2966    0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7744    0.6789    1.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250    0.9005    0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3922   -0.4009   -0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3397   -0.1819   -1.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9805   -1.0991   -1.8488 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5044    1.1408    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0092    1.1642    1.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9402    1.9623    0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3229   -0.5581    1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7048   -1.0028    0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7854    0.1484   -1.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199   -0.0473   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4811   -0.4517    1.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5601   -1.4010    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5487    1.7032    0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203    1.5505    0.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7185   -1.5086    0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3825   -0.6569    0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033   -0.3176   -2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2802   -0.5890   -2.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137   -1.8752   -0.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166   -1.2741    0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436    1.0995   -0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4759    0.1675   -1.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0215   -0.3522    1.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0409   -1.3177    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2949    1.6364    1.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3439    0.2964    2.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5133    1.6056    0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2184    1.3649   -0.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9268   -0.7986    0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5845   -1.1126   -0.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4513    0.8154   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
M  END


  Mrv1652309092220062D          

 18 17  0  0  0  0            999 V2000
    0.7420    4.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121    4.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    3.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    2.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323    1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724    2.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825    2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0288420

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/C\C=C/CCCCCCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18/h3-4,6-7,9-10,17H,2,5,8,11-16H2,1H3/b4-3-,7-6-,10-9-

> <INCHI_KEY>
NIPNNUONNZABRE-PDBXOOCHSA-N

> <FORMULA>
C17H28O

> <MOLECULAR_WEIGHT>
248.41

> <EXACT_MASS>
248.214015522

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
31.380014615866173

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8Z,11Z,14Z)-heptadeca-8,11,14-trienal

> <JCHEM_LOGP>
5.4567702203333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.785380090596878

> <JCHEM_PKA_STRONGEST_BASIC>
-6.94430599963006

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
84.109

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
heptadecatrienal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.385   9.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.889   7.736   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.881   6.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.385   5.117   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.897   4.826   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.401   3.371   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.914   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.922   4.244   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.434   3.953   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.938   2.498   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.434  -0.121   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.946  -0.413   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.954   0.752   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.467   0.461   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.475   1.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.987   1.334   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.995   2.498   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   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
(8Z,11Z,14Z)-8,11,14-Heptadecatrienal	ChEBI
8Z,11Z,14Z-Heptadecatrienal	ChEBI
Heptadecatrienal	ChEBI
Norlinolenic aldehyde	ChEBI

Chemical Formula

C₁₇H₂₈O

Average Mass

248.4100 Da

Monoisotopic Mass

248.21402 Da

IUPAC Name

(8Z,11Z,14Z)-heptadeca-8,11,14-trienal

Traditional Name

heptadecatrienal

CAS Registry Number

Not Available

SMILES

CC\C=C/C\C=C/C\C=C/CCCCCCC=O

InChI Identifier

InChI=1S/C17H28O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18/h3-4,6-7,9-10,17H,2,5,8,11-16H2,1H3/b4-3-,7-6-,10-9-

InChI Key

NIPNNUONNZABRE-PDBXOOCHSA-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
Nicotiana tabacum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty aldehydes. These are long chain aldehydes with a chain of at least 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty aldehydes

Direct Parent

Fatty aldehydes

Alternative Parents

Substituents

Fatty 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

polyunsaturated fatty aldehyde (CHEBI:76151 )
Fatty aldehydes (LMFA06000111 )

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	5.46	ChemAxon
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-6.9	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	12	ChemAxon
Refractivity	84.11 m³·mol⁻¹	ChemAxon
Polarizability	31.38 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4935450

KEGG Compound ID

C16343

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6430107

PDB ID

Not Available

ChEBI ID

76151

Good Scents ID

Not Available

References

General References

Thabet AA, Youssef FS, El-Shazly M, B Singab AN: GC-MS and GC-FID analyses of the volatile constituents of Brachychiton rupestris and Brachychiton discolor, their biological activities and their differentiation using multivariate data analysis. Nat Prod Res. 2020 Feb;34(4):590-594. doi: 10.1080/14786419.2018.1490908. Epub 2018 Nov 16. [PubMed:30445846 ]
Miyazawa M, Horiuchi E, Kawata J: Components of the essential oil from Matteuccia struthiopteris. J Oleo Sci. 2007;56(9):457-61. doi: 10.5650/jos.56.457. [PubMed:17898513 ]
Akakabe Y, Washizu K, Matsui K, Kajiwara T: Concise synthesis of (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, components of the essential oil of marine green alga Ulva pertusa. Biosci Biotechnol Biochem. 2005 Jul;69(7):1348-52. doi: 10.1271/bbb.69.1348. [PubMed:16041141 ]
Kawasaki W, Matsui K, Akakabe Y, Itai N, Kajiwara T: Long-chain aldehyde-forming activity in tobacco leaves. Phytochemistry. 1998 Nov 20;49(6):1565-1568. doi: 10.1016/s0031-9422(98)00236-2. [PubMed:11711065 ]
LOTUS database [Link]

Showing NP-Card for (8z,11z,14z)-heptadecatrienal (NP0288420)

MOL for NP0288420 ((8z,11z,14z)-heptadecatrienal)

3D MOL for NP0288420 ((8z,11z,14z)-heptadecatrienal)

3D SDF for NP0288420 ((8z,11z,14z)-heptadecatrienal)

3D-SDF for NP0288420 ((8z,11z,14z)-heptadecatrienal)

PDB for NP0288420 ((8z,11z,14z)-heptadecatrienal)

3D PDB for NP0288420 ((8z,11z,14z)-heptadecatrienal)

SMILES for NP0288420 ((8z,11z,14z)-heptadecatrienal)

INCHI for NP0288420 ((8z,11z,14z)-heptadecatrienal)

Structure for NP0288420 ((8z,11z,14z)-heptadecatrienal)

3D Structure for NP0288420 ((8z,11z,14z)-heptadecatrienal)