NP-MRD: Showing NP-Card for (9z,12z)-octadeca-9,12-dienoyl chloride (NP0244059)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 04:45:19 UTC

Updated at

2022-09-07 04:45:20 UTC

NP-MRD ID

NP0244059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9z,12z)-octadeca-9,12-dienoyl chloride

Description

Linoleoyl chloride belongs to the class of organic compounds known as acyl chlorides. These are organic compounds containing the functional group -CO-Cl. (9z,12z)-octadeca-9,12-dienoyl chloride is found in Schizonepeta tenuifolia. (9z,12z)-octadeca-9,12-dienoyl chloride was first documented in 2011 (PMID: 21852748). Based on a literature review very few articles have been published on Linoleoyl chloride (PMID: 23862153).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
   -7.2503    0.8049    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1961    0.0361   -1.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4369   -1.2253   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0074   -1.3197   -0.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1677   -0.9616    0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9898    0.3712    0.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8014    1.0123    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5610    0.4122    0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    0.3235    1.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192    0.9157    1.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506    1.7441    0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3090    1.1183   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4069    1.0630    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6130    0.4378   -0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7826    0.3362    0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9574   -0.2604    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -1.6286   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8367   -2.1915   -1.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8285   -1.5230   -1.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7093   -3.7951   -1.8539 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -8.3413    1.0629    0.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9681    0.1896    1.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7159    1.7622    0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7431    0.7118   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2624   -0.1093   -1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7461   -1.6951   -2.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9926   -1.9842   -0.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5679   -0.8358   -1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7349   -2.4293   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1851   -1.5211    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6810   -1.5366    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7667    0.9791    1.1983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7613    2.0360    1.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -0.5527   -0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331    1.0842   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8005   -0.2876    2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120    0.7864    2.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417    2.7517    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    2.0113   -0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5774    1.6781   -1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    0.0604   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    2.0528    0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038    0.3617    1.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9107    1.0906   -1.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2878   -0.5794   -0.5369 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0211    1.3343    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5534   -0.3339    1.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1479    0.4205   -0.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8766   -0.2416    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996   -1.6173   -1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2980   -2.3197    0.2948 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  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  1  0
 18 20  1  0
 18 19  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
M  END


  Mrv1652309072206452D          

 20 19  0  0  0  0            999 V2000
    2.9980    7.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 Cl  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  1  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  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/CCCCCCCC(Cl)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H31ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3/b7-6-,10-9-

> <INCHI_KEY>
FBWMYSQUTZRHAT-HZJYTTRNSA-N

> <FORMULA>
C18H31ClO

> <MOLECULAR_WEIGHT>
298.9

> <EXACT_MASS>
298.2063433

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.81051320097817

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z,12Z)-octadeca-9,12-dienoyl chloride

> <JCHEM_LOGP>
6.955206439333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.146087302752484

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
92.37729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,12Z)-octadeca-9,12-dienoyl chloride

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       5.596  14.011   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.263  13.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.263  11.701   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.929  10.931   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.929   9.391   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.595   8.621   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.595   7.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929   6.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   20 Cl   UNK     0      14.932   2.461   0.000  0.00  0.00          Cl+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   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₁ClO

Average Mass

298.9000 Da

Monoisotopic Mass

298.20634 Da

IUPAC Name

(9Z,12Z)-octadeca-9,12-dienoyl chloride

Traditional Name

(9Z,12Z)-octadeca-9,12-dienoyl chloride

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(Cl)=O

InChI Identifier

InChI=1S/C18H31ClO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3/b7-6-,10-9-

InChI Key

FBWMYSQUTZRHAT-HZJYTTRNSA-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
Schizonepeta tenuifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl chlorides. These are organic compounds containing the functional group -CO-Cl.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Acyl halides

Sub Class

Acyl chlorides

Direct Parent

Acyl chlorides

Alternative Parents

Substituents

Acyl chloride
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
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	6.96	ChemAxon
pKa (Strongest Basic)	-9.1	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	14	ChemAxon
Refractivity	92.38 m³·mol⁻¹	ChemAxon
Polarizability	36.81 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

7993504

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9817754

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xie J, Teng L, Yang Z, Zhou C, Liu Y, Yung BC, Lee RJ: A polyethylenimine-linoleic acid conjugate for antisense oligonucleotide delivery. Biomed Res Int. 2013;2013:710502. doi: 10.1155/2013/710502. Epub 2013 Jun 1. [PubMed:23862153 ]
Sato S, Habe H, Fukuoka T, Kitamoto D, Sakaki K: Synthesis of dilinoleoyl-D-glyceric acid and evaluation of its cytotoxicity to human dermal fibroblast and endothelial cells. J Oleo Sci. 2011;60(9):483-7. doi: 10.5650/jos.60.483. [PubMed:21852748 ]
LOTUS database [Link]

Showing NP-Card for (9z,12z)-octadeca-9,12-dienoyl chloride (NP0244059)

MOL for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

3D MOL for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

3D SDF for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

3D-SDF for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

PDB for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

3D PDB for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

SMILES for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

INCHI for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

Structure for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)

3D Structure for NP0244059 ((9z,12z)-octadeca-9,12-dienoyl chloride)