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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:46:57 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034007

Secondary Accession Numbers

HMDB34007

Metabolite Identification

Common Name

(E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol

Description

(E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol has been detected, but not quantified in, fats and oils and herbs and spices. This could make (e,e)-1-chloro-3,11-tridecadiene-5,7,9-triyn-2-ol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv0541 05061307302D          

 15 14  0  0  0  0            999 V2000
    4.9500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  3  0  0  0  0
  6  5  1  0  0  0  0
  7  6  3  0  0  0  0
  8  7  1  0  0  0  0
  9  8  3  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034007

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C/C#CC#CC#C\C=C\C(O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C13H11ClO/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14/h2-3,10-11,13,15H,12H2,1H3/b3-2-,11-10+

> <INCHI_KEY>
BWFFGWCCMCLGBQ-JSQGHLFOSA-N

> <FORMULA>
C13H11ClO

> <MOLECULAR_WEIGHT>
218.679

> <EXACT_MASS>
218.049842681

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
24.69954802714937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,11Z)-1-chlorotrideca-3,11-dien-5,7,9-triyn-2-ol

> <ALOGPS_LOGP>
3.78

> <JCHEM_LOGP>
3.272312320666667

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.94523962154788

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2601521895349563

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
68.1198

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,11Z)-1-chlorotrideca-3,11-dien-5,7,9-triyn-2-ol

> <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       9.240   8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.470   9.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.930   9.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.160   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.390   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -3.080  -2.667   0.000  0.00  0.00          Cl+0
HETATM   15  O   UNK     0       0.000  -2.667   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   13                                                       
CONECT   12   13   14                                                       
CONECT   13   11   12   15                                                  
CONECT   14   12                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0034007
HETATM    1  C1  UNL     1      -6.360  -0.823  -0.061  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.844   0.576   0.113  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.013   1.571   0.351  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.611   1.296   0.443  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.416   1.071   0.504  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.022   0.829   0.581  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.822   0.641   0.648  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.579   0.435   0.744  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.774   0.276   0.839  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.193   0.104   0.968  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.957  -0.082  -0.095  1.00  0.00           C  
HETATM   12  C12 UNL     1       5.422  -0.256   0.077  1.00  0.00           C  
HETATM   13  O1  UNL     1       5.657  -1.268   0.998  1.00  0.00           O  
HETATM   14  C13 UNL     1       6.078  -0.543  -1.246  1.00  0.00           C  
HETATM   15 CL1  UNL     1       5.386  -2.038  -1.922  1.00  0.00          CL  
HETATM   16  H1  UNL     1      -6.089  -0.945  -1.149  1.00  0.00           H  
HETATM   17  H2  UNL     1      -5.447  -1.017   0.542  1.00  0.00           H  
HETATM   18  H3  UNL     1      -7.148  -1.556   0.201  1.00  0.00           H  
HETATM   19  H4  UNL     1      -7.918   0.797   0.044  1.00  0.00           H  
HETATM   20  H5  UNL     1      -6.426   2.559   0.467  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.684   0.121   1.932  1.00  0.00           H  
HETATM   22  H7  UNL     1       3.539  -0.111  -1.097  1.00  0.00           H  
HETATM   23  H8  UNL     1       5.885   0.682   0.482  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.970  -1.965   0.982  1.00  0.00           H  
HETATM   25  H10 UNL     1       5.820   0.294  -1.936  1.00  0.00           H  
HETATM   26  H11 UNL     1       7.172  -0.649  -1.092  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   19
CONECT    3    4   20
CONECT    4    5    5    5
CONECT    5    6
CONECT    6    7    7    7
CONECT    7    8
CONECT    8    9    9    9
CONECT    9   10
CONECT   10   11   11   21
CONECT   11   12   22
CONECT   12   13   14   23
CONECT   13   24
CONECT   14   15   25   26
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₁ClO

Average Molecular Weight

218.679

Monoisotopic Molecular Weight

218.049842681

IUPAC Name

(3E,11Z)-1-chlorotrideca-3,11-dien-5,7,9-triyn-2-ol

Traditional Name

(3E,11Z)-1-chlorotrideca-3,11-dien-5,7,9-triyn-2-ol

CAS Registry Number

Not Available

SMILES

C\C=C/C#CC#CC#C\C=C\C(O)CCl

InChI Identifier

InChI=1S/C13H11ClO/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14/h2-3,10-11,13,15H,12H2,1H3/b3-2-,11-10+

InChI Key

BWFFGWCCMCLGBQ-JSQGHLFOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Halohydrins

Sub Class

Chlorohydrins

Direct Parent

Chlorohydrins

Alternative Parents

Substituents

Secondary alcohol
Chlorohydrin
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Alkyl halide
Alkyl chloride
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034007)
Cell membrane (HMDB: HMDB0034007)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034007)

Source

Exogenous

Exogenous (HMDB: HMDB0034007)

Food

Food (HMDB: HMDB0034007)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0034007)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034007)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	83 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	3.78	ALOGPS
logP	3.27	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.95	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	68.12 m³·mol⁻¹	ChemAxon
Polarizability	24.7 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	143.525	30932474
DeepCCS	[M-H]-	141.129	30932474
DeepCCS	[M-2H]-	175.581	30932474
DeepCCS	[M+Na]+	150.167	30932474
AllCCS	[M+H]+	147.8	32859911
AllCCS	[M+H-H2O]+	144.0	32859911
AllCCS	[M+NH4]+	151.4	32859911
AllCCS	[M+Na]+	152.4	32859911
AllCCS	[M-H]-	143.9	32859911
AllCCS	[M+Na-2H]-	144.6	32859911
AllCCS	[M+HCOO]-	145.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol	C\C=C/C#CC#CC#C\C=C\C(O)CCl	2952.1	Standard polar	33892256
(E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol	C\C=C/C#CC#CC#C\C=C\C(O)CCl	1949.8	Standard non polar	33892256
(E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol	C\C=C/C#CC#CC#C\C=C\C(O)CCl	2069.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol,1TMS,isomer #1	C/C=C\C#CC#CC#C/C=C/C(CCl)O[Si](C)(C)C	2051.2	Semi standard non polar	33892256
(E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol,1TBDMS,isomer #1	C/C=C\C#CC#CC#C/C=C/C(CCl)O[Si](C)(C)C(C)(C)C	2269.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-2900000000-5be7e508fbe7785c03fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol GC-MS (1 TMS) - 70eV, Positive	splash10-009l-9230000000-85e291ef9def47a8937d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 10V, Positive-QTOF	splash10-0uxr-0290000000-1aaa0889a1b9b9ab3c2c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 20V, Positive-QTOF	splash10-016r-4940000000-dd494a68c1dd92f9dae9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 40V, Positive-QTOF	splash10-0v0c-9500000000-91db9066e9cc1d21ad74	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 10V, Negative-QTOF	splash10-014i-0290000000-ef255ea84e43ef481689	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 20V, Negative-QTOF	splash10-015a-0920000000-36b7557237f7184a07c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 40V, Negative-QTOF	splash10-02d0-6900000000-dc71a4b4c282d0c88dc8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 10V, Negative-QTOF	splash10-014i-0190000000-3080194f1954cfd3eb4f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 20V, Negative-QTOF	splash10-001i-9100000000-7f93922301798045b1f1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 40V, Negative-QTOF	splash10-03ea-9600000000-4a1582eedb3674ce8f34	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 10V, Positive-QTOF	splash10-014i-3190000000-50bae8a617816f40557a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 20V, Positive-QTOF	splash10-01t9-9500000000-cfce7fda8f5635b57247	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol 40V, Positive-QTOF	splash10-007a-9800000000-14d3fc459ad46e0b212f	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012243

KNApSAcK ID

Not Available

Chemspider ID

35013685

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751511

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol (HMDB0034007)

MOL for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

3D MOL for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

3D SDF for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

3D-SDF for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

PDB for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

3D PDB for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

SMILES for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

INCHI for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

Structure for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

3D Structure for HMDB0034007 ((E,E)-1-Chloro-3,11-tridecadiene-5,7,9-triyn-2-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra