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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:15:18 UTC

Update Date

2021-09-26 22:51:31 UTC

HMDB ID

HMDB0244060

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Sebacil

Description

Sebacil, also known as baythion or sebacil pour-ON, belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Based on a literature review very few articles have been published on Sebacil. This compound has been identified in human blood as reported by (PMID: 31557052 ). Sebacil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Sebacil is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       3.777  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -2.006   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.188  -1.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.818  -0.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.928   0.984   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.558   2.478   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.078   2.906   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   3.546   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.297   5.041   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.147   3.119   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.517   1.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.407   0.556   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    1                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0244060
HETATM    1  O1  UNL     1      -1.010   2.482   1.657  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.353   1.983   0.692  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.040   1.792  -0.591  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.894   0.561  -0.638  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.520  -0.436   0.449  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.084  -1.750  -0.096  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.264  -2.210   0.244  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.300  -1.164   0.511  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.576  -0.268  -0.652  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.853   1.163  -0.261  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.057   1.616   0.888  1.00  0.00           C  
HETATM   12  O2  UNL     1       1.505   1.717   2.061  1.00  0.00           O  
HETATM   13  H1  UNL     1      -1.705   2.676  -0.782  1.00  0.00           H  
HETATM   14  H2  UNL     1      -0.281   1.822  -1.405  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.659   0.046  -1.615  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.954   0.798  -0.663  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.460  -0.561   1.066  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.793   0.007   1.164  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.824  -2.548   0.212  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.216  -1.703  -1.218  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.657  -2.839  -0.609  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.275  -2.913   1.120  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.127  -0.615   1.462  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.261  -1.731   0.707  1.00  0.00           H  
HETATM   25  H13 UNL     1       2.494  -0.595  -1.226  1.00  0.00           H  
HETATM   26  H14 UNL     1       0.751  -0.357  -1.393  1.00  0.00           H  
HETATM   27  H15 UNL     1       1.741   1.806  -1.133  1.00  0.00           H  
HETATM   28  H16 UNL     1       2.930   1.221   0.048  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   13   14
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   27   28
CONECT   11   12   12
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Baythion	HMDB
Sebacil pour-ON	HMDB
Valekson	HMDB
Valexon	HMDB
Phenylglyoxylonitrile oxime O,O-diethylphosphorothioate	HMDB
Phoxim	HMDB

Chemical Formula

C₁₀H₁₆O₂

Average Molecular Weight

168.236

Monoisotopic Molecular Weight

168.115029755

IUPAC Name

cyclodecane-1,2-dione

Traditional Name

sebacil

CAS Registry Number

Not Available

SMILES

O=C1CCCCCCCCC1=O

InChI Identifier

InChI=1S/C10H16O2/c11-9-7-5-3-1-2-4-6-8-10(9)12/h1-8H2

InChI Key

HLPUHEJQIIHQDF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.82	ALOGPS
logP	3.11	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	17	ChemAxon
pKa (Strongest Basic)	-8.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.4 m³·mol⁻¹	ChemAxon
Polarizability	18.63 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	143.024	30932474
DeepCCS	[M-H]-	139.704	30932474
DeepCCS	[M-2H]-	176.575	30932474
DeepCCS	[M+Na]+	151.996	30932474
AllCCS	[M+H]+	137.7	32859911
AllCCS	[M+H-H2O]+	133.3	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	141.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	15.3006 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.74 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1996.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	496.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	300.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	560.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	631.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1419.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	396.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1243.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	406.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	518.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	448.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	63.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sebacil	O=C1CCCCCCCCC1=O	2123.3	Standard polar	33892256
Sebacil	O=C1CCCCCCCCC1=O	1416.5	Standard non polar	33892256
Sebacil	O=C1CCCCCCCCC1=O	1502.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sebacil,1TMS,isomer #1	C[Si](C)(C)OC1=CCCCCCCCC1=O	1673.5	Semi standard non polar	33892256
Sebacil,1TMS,isomer #1	C[Si](C)(C)OC1=CCCCCCCCC1=O	1546.6	Standard non polar	33892256
Sebacil,1TMS,isomer #1	C[Si](C)(C)OC1=CCCCCCCCC1=O	2102.6	Standard polar	33892256
Sebacil,2TMS,isomer #1	C[Si](C)(C)OC1=CCCCCCCC=C1O[Si](C)(C)C	1757.8	Semi standard non polar	33892256
Sebacil,2TMS,isomer #1	C[Si](C)(C)OC1=CCCCCCCC=C1O[Si](C)(C)C	1722.6	Standard non polar	33892256
Sebacil,2TMS,isomer #1	C[Si](C)(C)OC1=CCCCCCCC=C1O[Si](C)(C)C	2311.0	Standard polar	33892256
Sebacil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCCCCCCC1=O	1882.2	Semi standard non polar	33892256
Sebacil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCCCCCCC1=O	1702.4	Standard non polar	33892256
Sebacil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCCCCCCC1=O	2319.3	Standard polar	33892256
Sebacil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCCCCCC=C1O[Si](C)(C)C(C)(C)C	2218.1	Semi standard non polar	33892256
Sebacil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCCCCCC=C1O[Si](C)(C)C(C)(C)C	1974.5	Standard non polar	33892256
Sebacil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CCCCCCCC=C1O[Si](C)(C)C(C)(C)C	2580.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sebacil GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0900000000-a4b2e609ffe422fd4168	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sebacil 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 - Sebacil 10V, Positive-QTOF	splash10-014i-0900000000-f9b2951dd69b378c6031	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sebacil 20V, Positive-QTOF	splash10-014i-0900000000-bccaa6b294a0a1cca7c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sebacil 40V, Positive-QTOF	splash10-001i-0900000000-931cad0ad7cbfb8f9916	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sebacil 10V, Negative-QTOF	splash10-014i-0900000000-cb7592114e600c180aec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sebacil 20V, Negative-QTOF	splash10-014i-0900000000-cb7592114e600c180aec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sebacil 40V, Negative-QTOF	splash10-014i-0900000000-a3f3b8148b09fe443e62	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

87436

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phoxim

METLIN ID

Not Available

PubChem Compound

96839

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Sebacil (HMDB0244060)

MOL for HMDB0244060 (Sebacil)

3D MOL for HMDB0244060 (Sebacil)

3D SDF for HMDB0244060 (Sebacil)

3D-SDF for HMDB0244060 (Sebacil)

PDB for HMDB0244060 (Sebacil)

3D PDB for HMDB0244060 (Sebacil)

SMILES for HMDB0244060 (Sebacil)

INCHI for HMDB0244060 (Sebacil)

Structure for HMDB0244060 (Sebacil)

3D Structure for HMDB0244060 (Sebacil)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra