Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-03-07 21:34:55 UTC

Update Date

2022-03-07 03:17:37 UTC

HMDB ID

HMDB0059885

Secondary Accession Numbers

HMDB59885

Metabolite Identification

Common Name

p-Menth-1-en-9-al

Description

p-Menth-1-en-9-al belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. p-Menth-1-en-9-al is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

COMPND    HMDB0059885
HETATM    1  C1  UNL     1       3.643   0.026  -0.244  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.190   0.214  -0.081  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.495   1.012  -0.883  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.046   1.153  -0.663  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.637  -0.184  -0.422  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.961   0.154   0.228  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.791  -1.036   0.548  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.707   0.995  -0.754  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.596   2.203  -0.745  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.187  -1.124   0.391  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.418  -0.482   0.994  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.227   0.697   0.434  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.958   0.287  -1.277  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.949  -1.038  -0.074  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.974   1.553  -1.685  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.081   1.816   0.242  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.431   1.618  -1.549  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.822  -0.611  -1.441  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.805   0.756   1.130  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.851  -0.675   0.674  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.818  -1.773  -0.295  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.537  -1.522   1.518  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.373   0.546  -1.505  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.547  -1.994  -0.210  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.384  -1.577   1.243  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.042  -1.269   1.442  1.00  0.00           H  
HETATM   27  H16 UNL     1       1.121   0.252   1.774  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   11
CONECT    3    4   15
CONECT    4    5   16   17
CONECT    5    6   10   18
CONECT    6    7    8   19
CONECT    7   20   21   22
CONECT    8    9    9   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha,4-Dimethyl-3-cyclohexene-1-acetaldehyde	ChEBI
a,4-Dimethyl-3-cyclohexene-1-acetaldehyde	Generator
Α,4-dimethyl-3-cyclohexene-1-acetaldehyde	Generator
2-(4-Methylcyclohex-3-en-1-yl)propanal	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

2-(4-methylcyclohex-3-en-1-yl)propanal

Traditional Name

2-(4-methylcyclohex-3-en-1-yl)propanal

CAS Registry Number

Not Available

SMILES

CC(C=O)C1CCC(C)=CC1

InChI Identifier

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

InChI Key

UMEJBWOWZDRULR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

aldehyde (CHEBI:87568 )
monoterpenoid (CHEBI:87568 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0059885)

Source

Endogenous

Endogenous (HMDB: HMDB0059885)

Animal

Animal (HMDB: HMDB0059885)

Exogenous

Food

Food (HMDB: HMDB0059885)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Fruit

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0059885)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0059885)

Lipid metabolism pathway (HMDB: HMDB0059885)

Cellular process

Cell signaling (HMDB: HMDB0059885)

Biochemical process

Lipid transport (HMDB: HMDB0059885)

Role

Biological role

Energy source (HMDB: HMDB0059885)

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	0.62 g/L	ALOGPS
logP	2.8	ALOGPS
logP	2.34	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	16.14	ChemAxon
pKa (Strongest Basic)	-7	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	47.47 m³·mol⁻¹	ChemAxon
Polarizability	18.35 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]+	135.448	31661259
DarkChem	[M-H]-	130.608	31661259
DeepCCS	[M+H]+	136.577	30932474
DeepCCS	[M-H]-	133.305	30932474
DeepCCS	[M-2H]-	170.345	30932474
DeepCCS	[M+Na]+	145.758	30932474
AllCCS	[M+H]+	133.6	32859911
AllCCS	[M+H-H2O]+	129.1	32859911
AllCCS	[M+NH4]+	137.7	32859911
AllCCS	[M+Na]+	138.9	32859911
AllCCS	[M-H]-	138.3	32859911
AllCCS	[M+Na-2H]-	139.9	32859911
AllCCS	[M+HCOO]-	141.6	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.	5.44 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3898 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.24 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2072.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	526.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	324.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	572.1 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	696.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	135.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1220.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	428.7 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	1188.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	449.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	531.6 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	23.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Menth-1-en-9-al	CC(C=O)C1CCC(C)=CC1	1622.1	Standard polar	33892256
p-Menth-1-en-9-al	CC(C=O)C1CCC(C)=CC1	1160.3	Standard non polar	33892256
p-Menth-1-en-9-al	CC(C=O)C1CCC(C)=CC1	1219.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-Menth-1-en-9-al,1TMS,isomer #1	CC1=CCC(C(C)=CO[Si](C)(C)C)CC1	1427.3	Semi standard non polar	33892256
p-Menth-1-en-9-al,1TMS,isomer #1	CC1=CCC(C(C)=CO[Si](C)(C)C)CC1	1337.7	Standard non polar	33892256
p-Menth-1-en-9-al,1TMS,isomer #1	CC1=CCC(C(C)=CO[Si](C)(C)C)CC1	1567.7	Standard polar	33892256
p-Menth-1-en-9-al,1TBDMS,isomer #1	CC1=CCC(C(C)=CO[Si](C)(C)C(C)(C)C)CC1	1647.8	Semi standard non polar	33892256
p-Menth-1-en-9-al,1TBDMS,isomer #1	CC1=CCC(C(C)=CO[Si](C)(C)C(C)(C)C)CC1	1541.9	Standard non polar	33892256
p-Menth-1-en-9-al,1TBDMS,isomer #1	CC1=CCC(C(C)=CO[Si](C)(C)C(C)(C)C)CC1	1746.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - p-Menth-1-en-9-al GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fms-9300000000-0d49394b559ba6199baa	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Menth-1-en-9-al 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 - p-Menth-1-en-9-al 10V, Positive-QTOF	splash10-0udi-1900000000-903602d539295a644af9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 20V, Positive-QTOF	splash10-0udj-9400000000-f34fa46f1e09aa9109a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 40V, Positive-QTOF	splash10-1000-9100000000-3b924c6fae097e08065e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 10V, Negative-QTOF	splash10-0udi-0900000000-a8d40e3d45e74d8dc776	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 20V, Negative-QTOF	splash10-0udi-2900000000-1d7306396387a961007e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 40V, Negative-QTOF	splash10-0a4j-9100000000-cc98e77a75a473bfe66f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 10V, Positive-QTOF	splash10-0079-5900000000-b169ed24cb0655404c3f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 20V, Positive-QTOF	splash10-05fs-9600000000-503fe293e463800d6911	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 40V, Positive-QTOF	splash10-0006-9000000000-dba2ae2fcfc1be12405c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 10V, Negative-QTOF	splash10-00di-0900000000-6f4efea561d738bfac89	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 20V, Negative-QTOF	splash10-00xr-0900000000-5c46aa2f58bfa7fc7f64	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Menth-1-en-9-al 40V, Negative-QTOF	splash10-0avl-3900000000-d56f2eaae39ed9398c23	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

FDB009776

KNApSAcK ID

Not Available

Chemspider ID

453972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

520440

PDB ID

Not Available

ChEBI ID

87568

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for p-Menth-1-en-9-al (HMDB0059885)

MOL for HMDB0059885 (p-Menth-1-en-9-al)

3D MOL for HMDB0059885 (p-Menth-1-en-9-al)

3D SDF for HMDB0059885 (p-Menth-1-en-9-al)

3D-SDF for HMDB0059885 (p-Menth-1-en-9-al)

PDB for HMDB0059885 (p-Menth-1-en-9-al)

3D PDB for HMDB0059885 (p-Menth-1-en-9-al)

SMILES for HMDB0059885 (p-Menth-1-en-9-al)

INCHI for HMDB0059885 (p-Menth-1-en-9-al)

Structure for HMDB0059885 (p-Menth-1-en-9-al)

3D Structure for HMDB0059885 (p-Menth-1-en-9-al)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra