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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:13:31 UTC

Update Date

2021-09-26 23:12:32 UTC

HMDB ID

HMDB0256677

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isohexylcyanoacrylate

Description

Isohexylcyanoacrylate, also known as PIHCA, belongs to the class of organic compounds known as cyanoacrylates. These are organonitrogen compounds containing an acrylic acid ester, which carries a nitrile group. They have the general structure ROC(=O)C(=C)C#N, where R is an organic group. Based on a literature review very few articles have been published on Isohexylcyanoacrylate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isohexylcyanoacrylate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isohexylcyanoacrylate 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                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       4.263  -4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.596  -4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.596  -6.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.930  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.264  -4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.597  -4.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.931  -4.771   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.265  -4.001   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.265  -2.461   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      13.598  -4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.598  -6.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.932  -4.001   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      16.266  -3.231   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0256677
HETATM    1  C1  UNL     1       4.480  -0.257   1.383  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.510   0.147   0.135  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.743   0.450  -0.501  1.00  0.00           C  
HETATM    4  N1  UNL     1       6.748   0.716  -1.016  1.00  0.00           N  
HETATM    5  C4  UNL     1       3.273   0.282  -0.592  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.301   0.668  -1.787  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.031   0.011  -0.058  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.822   0.138  -0.753  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.362  -0.235   0.111  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.663  -0.095  -0.649  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.854  -0.455   0.177  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.089  -0.278  -0.683  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.001   0.398   1.410  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.558  -0.495   1.896  1.00  0.00           H  
HETATM   15  H2  UNL     1       5.389  -0.369   1.957  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.642   1.167  -1.131  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.793  -0.540  -1.642  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.389   0.286   1.064  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.254  -1.335   0.336  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.679  -0.724  -1.560  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.761   0.945  -0.970  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.850  -1.542   0.475  1.00  0.00           H  
HETATM   23  H10 UNL     1      -4.994  -0.056  -0.082  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.882   0.542  -1.393  1.00  0.00           H  
HETATM   25  H12 UNL     1      -4.230  -1.206  -1.295  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.576   1.412   1.261  1.00  0.00           H  
HETATM   27  H14 UNL     1      -2.607  -0.114   2.306  1.00  0.00           H  
HETATM   28  H15 UNL     1      -4.100   0.540   1.598  1.00  0.00           H  
CONECT    1    2    2   14   15
CONECT    2    3    5
CONECT    3    4    4    4
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   16   17
CONECT    9   10   18   19
CONECT   10   11   20   21
CONECT   11   12   13   22
CONECT   12   23   24   25
CONECT   13   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isohexylcyanoacrylic acid	Generator
4-Methylpentyl 2-cyanoprop-2-enoic acid	HMDB
PIHCA	HMDB
Polyisohexylcyanoacrylate	HMDB

Chemical Formula

C₁₀H₁₅NO₂

Average Molecular Weight

181.235

Monoisotopic Molecular Weight

181.110278727

IUPAC Name

4-methylpentyl 2-cyanoprop-2-enoate

Traditional Name

4-methylpentyl 2-cyanoprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(C)CCCOC(=O)C(=C)C#N

InChI Identifier

InChI=1S/C10H15NO2/c1-8(2)5-4-6-13-10(12)9(3)7-11/h8H,3-6H2,1-2H3

InChI Key

HFQQYIUTYJVYFZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanoacrylates. These are organonitrogen compounds containing an acrylic acid ester, which carries a nitrile group. They have the general structure ROC(=O)C(=C)C#N, where R is an organic group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Cyanoacrylates

Alternative Parents

Substituents

Cyanoacrylic acid ester
Nitrile
Carbonitrile
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.7	ALOGPS
logP	2.78	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	50.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	50.14 m³·mol⁻¹	ChemAxon
Polarizability	20.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	146.633	30932474
DeepCCS	[M-H]-	143.793	30932474
DeepCCS	[M-2H]-	180.728	30932474
DeepCCS	[M+Na]+	156.047	30932474
AllCCS	[M+H]+	142.9	32859911
AllCCS	[M+H-H2O]+	139.2	32859911
AllCCS	[M+NH4]+	146.4	32859911
AllCCS	[M+Na]+	147.3	32859911
AllCCS	[M-H]-	143.5	32859911
AllCCS	[M+Na-2H]-	145.0	32859911
AllCCS	[M+HCOO]-	146.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.8 minutes	32390414
Predicted by Siyang on May 30, 2022	16.9602 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2355.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	576.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	212.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	364.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	286.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	691.2 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	771.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	171.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1361.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	494.5 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	1553.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	443.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	489.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	544.6 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	31.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isohexylcyanoacrylate	CC(C)CCCOC(=O)C(=C)C#N	1769.4	Standard polar	33892256
Isohexylcyanoacrylate	CC(C)CCCOC(=O)C(=C)C#N	1222.8	Standard non polar	33892256
Isohexylcyanoacrylate	CC(C)CCCOC(=O)C(=C)C#N	1315.1	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 - Isohexylcyanoacrylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-049e752967375c281912	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isohexylcyanoacrylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

97193

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108097

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 Isohexylcyanoacrylate (HMDB0256677)

MOL for HMDB0256677 (Isohexylcyanoacrylate)

3D MOL for HMDB0256677 (Isohexylcyanoacrylate)

3D SDF for HMDB0256677 (Isohexylcyanoacrylate)

3D-SDF for HMDB0256677 (Isohexylcyanoacrylate)

PDB for HMDB0256677 (Isohexylcyanoacrylate)

3D PDB for HMDB0256677 (Isohexylcyanoacrylate)

SMILES for HMDB0256677 (Isohexylcyanoacrylate)

INCHI for HMDB0256677 (Isohexylcyanoacrylate)

Structure for HMDB0256677 (Isohexylcyanoacrylate)

3D Structure for HMDB0256677 (Isohexylcyanoacrylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra