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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:02:43 UTC

Update Date

2023-02-21 17:29:21 UTC

HMDB ID

HMDB0059761

Secondary Accession Numbers

HMDB59761

Metabolite Identification

Common Name

4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde

Description

4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group. 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). These are compounds containing a non-aromatic closed ring of carbon atoms in which at least 2 atoms are connected by a double bond.

Structure

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

COMPND    HMDB0059761
HETATM    1  C1  UNL     1       1.676   1.489  -0.502  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.948   0.191  -0.630  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.995  -0.901  -0.707  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.034  -0.022   0.552  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.902  -0.031   1.778  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.391  -1.079   2.164  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.936   1.104   0.666  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.809   1.132  -0.561  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.334  -0.030  -0.911  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.066  -1.243  -0.134  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.716  -1.304   0.498  1.00  0.00           C  
HETATM   12  H1  UNL     1       1.052   2.368  -0.369  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.491   1.395   0.272  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.240   1.642  -1.465  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.393   0.141  -1.595  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.689  -0.590  -1.541  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.593  -1.871  -0.995  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.645  -0.924   0.198  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.098   0.882   2.322  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.641   0.847   1.508  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.512   2.074   0.907  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.985   2.051  -1.113  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.968  -0.082  -1.778  1.00  0.00           H  
HETATM   24  H13 UNL     1      -2.900  -1.322   0.625  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.244  -2.144  -0.793  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.882  -1.635   1.567  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.151  -2.139   0.036  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5    7   11
CONECT    5    6    6   19
CONECT    7    8   20   21
CONECT    8    9    9   22
CONECT    9   10   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

1-(propan-2-yl)cyclohex-3-ene-1-carbaldehyde

Traditional Name

1-isopropylcyclohex-3-ene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)C1(CCC=CC1)C=O

InChI Identifier

InChI=1S/C10H16O/c1-9(2)10(8-11)6-4-3-5-7-10/h3-4,8-9H,5-7H2,1-2H3

InChI Key

HSRWOAPOKHRLIT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxides

Sub Class

Not Available

Direct Parent

Organic oxides

Alternative Parents

Substituents

Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 22284503)

Cellular substructure

Membrane (HMDB: HMDB0059761)

Source

Exogenous

Exogenous (HMDB: HMDB0059761)

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
Water Solubility	0.097 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2.66	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-7.1	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	2	ChemAxon
Refractivity	47.69 m³·mol⁻¹	ChemAxon
Polarizability	17.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	133.992	31661259
DarkChem	[M-H]-	129.173	31661259
DeepCCS	[M+H]+	141.644	30932474
DeepCCS	[M-H]-	137.977	30932474
DeepCCS	[M-2H]-	175.523	30932474
DeepCCS	[M+Na]+	150.902	30932474
AllCCS	[M+H]+	133.1	32859911
AllCCS	[M+H-H2O]+	128.6	32859911
AllCCS	[M+NH4]+	137.2	32859911
AllCCS	[M+Na]+	138.4	32859911
AllCCS	[M-H]-	136.2	32859911
AllCCS	[M+Na-2H]-	137.8	32859911
AllCCS	[M+HCOO]-	139.6	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.	5.53 minutes	32390414
Predicted by Siyang on May 30, 2022	17.2257 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.57 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2198.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	566.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	217.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	393.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	406.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	715.1 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	673.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1464.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	510.7 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	1386.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	547.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	417.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	532.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	569.2 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	18.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde	CC(C)C1(CCC=CC1)C=O	1560.9	Standard polar	33892256
4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde	CC(C)C1(CCC=CC1)C=O	1130.2	Standard non polar	33892256
4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde	CC(C)C1(CCC=CC1)C=O	1178.2	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 - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-024u-8900000000-54136eacf01c4767cead	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 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 - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 10V, Positive-QTOF	splash10-0udi-0900000000-6e83fed479f3f3b38574	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 20V, Positive-QTOF	splash10-0w29-4900000000-072adad15d65f20a064e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 40V, Positive-QTOF	splash10-0gb9-9100000000-3a80d12f886c033245b5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 10V, Negative-QTOF	splash10-0udi-0900000000-b8fa18619dd333dc942b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 20V, Negative-QTOF	splash10-0udi-0900000000-b4ae3781714843164501	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 40V, Negative-QTOF	splash10-0ac0-4900000000-a8d1d2e1aa22d1d6c571	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 20V, Negative-QTOF	splash10-0udi-0900000000-c69055b6aa039453250d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 40V, Negative-QTOF	splash10-0002-6900000000-16de23393df3676d587f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 10V, Positive-QTOF	splash10-05cr-8900000000-503af9878cc0246c9373	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 20V, Positive-QTOF	splash10-00ec-9800000000-2dcef37f5857a1cfb81f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde 40V, Positive-QTOF	splash10-0006-9000000000-945708f3239a05c5437c	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124202117

PDB ID

Not Available

ChEBI ID

89872

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

Not Available

Showing metabocard for 4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde (HMDB0059761)

MOL for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

3D MOL for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

3D SDF for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

3D-SDF for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

PDB for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

3D PDB for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

SMILES for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

INCHI for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

Structure for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

3D Structure for HMDB0059761 (4-(1-Methylethyl)-1-cyclohexene-4-carboxaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra