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

2012-09-11 22:15:11 UTC

Update Date

2022-03-07 02:55:09 UTC

HMDB ID

HMDB0037010

Secondary Accession Numbers

HMDB37010

Metabolite Identification

Common Name

(2S,4R)-p-Mentha-1(7),8-dien-2-ol

Description

(2S,4R)-p-Mentha-1(7),8-dien-2-ol 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. Based on a literature review a small amount of articles have been published on (2S,4R)-p-Mentha-1(7),8-dien-2-ol.

Structure

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

COMPND    HMDB0037010
HETATM    1  C1  UNL     1       3.157   0.306   0.701  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.866   0.085   0.616  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.825   1.027   1.099  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.010   1.445  -0.094  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.574   0.298  -0.868  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.833  -0.125  -0.192  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.109  -1.363   0.171  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.886   0.926   0.109  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.351  -0.830  -1.114  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.284  -1.161   0.013  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.340  -1.954  -0.414  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.895  -0.398   0.340  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.517   1.217   1.143  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.318   1.927   1.496  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.204   0.590   1.906  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.815   2.082   0.281  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.659   2.096  -0.713  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.869   0.710  -1.855  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.475  -2.226   0.034  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.052  -1.584   0.660  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.730   1.294   1.118  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.908   0.512  -0.075  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.753   1.729  -0.647  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.023  -0.644  -2.008  1.00  0.00           H  
HETATM   25  H14 UNL     1      -0.190  -1.746  -1.381  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.759  -1.688   0.834  1.00  0.00           H  
HETATM   27  H16 UNL     1       1.987  -2.524  -1.159  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3   10
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6    9   18
CONECT    6    7    7    8
CONECT    7   19   20
CONECT    8   21   22   23
CONECT    9   10   24   25
CONECT   10   11   26
CONECT   11   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-trans-P-Mentha-1(7),8-dien-2-ol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

2-methylidene-5-(prop-1-en-2-yl)cyclohexan-1-ol

Traditional Name

2-methylidene-5-(prop-1-en-2-yl)cyclohexan-1-ol

CAS Registry Number

2102-62-7

SMILES

CC(=C)C1CCC(=C)C(O)C1

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h9-11H,1,3-6H2,2H3

InChI Key

PNVTXOFNJFHXOK-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
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037010)

Source

Endogenous

Endogenous (HMDB: HMDB0037010)

Plant

Plant (HMDB: HMDB0037010)

Animal

Animal (HMDB: HMDB0037010)

Exogenous

Food

Food (HMDB: HMDB0037010)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Spearmint (FooDB: FOOD00112)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037010)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037010)

Lipid metabolism pathway (HMDB: HMDB0037010)

Cellular process

Cell signaling (HMDB: HMDB0037010)

Biochemical process

Lipid transport (HMDB: HMDB0037010)

Role

Biological role

Energy source (HMDB: HMDB0037010)

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	1.71 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.05	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	18.21	ChemAxon
pKa (Strongest Basic)	-1.4	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	1	ChemAxon
Refractivity	46.92 m³·mol⁻¹	ChemAxon
Polarizability	18.21 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]+	135.099	31661259
DarkChem	[M-H]-	129.563	31661259
DeepCCS	[M+H]+	138.054	30932474
DeepCCS	[M-H]-	135.518	30932474
DeepCCS	[M-2H]-	171.857	30932474
DeepCCS	[M+Na]+	147.091	30932474
AllCCS	[M+H]+	134.4	32859911
AllCCS	[M+H-H2O]+	129.9	32859911
AllCCS	[M+NH4]+	138.5	32859911
AllCCS	[M+Na]+	139.7	32859911
AllCCS	[M-H]-	136.1	32859911
AllCCS	[M+Na-2H]-	137.6	32859911
AllCCS	[M+HCOO]-	139.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2S,4R)-p-Mentha-1(7),8-dien-2-ol	CC(=C)C1CCC(=C)C(O)C1	1793.3	Standard polar	33892256
(2S,4R)-p-Mentha-1(7),8-dien-2-ol	CC(=C)C1CCC(=C)C(O)C1	1205.9	Standard non polar	33892256
(2S,4R)-p-Mentha-1(7),8-dien-2-ol	CC(=C)C1CCC(=C)C(O)C1	1210.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2S,4R)-p-Mentha-1(7),8-dien-2-ol,1TMS,isomer #1	C=C(C)C1CCC(=C)C(O[Si](C)(C)C)C1	1279.1	Semi standard non polar	33892256
(2S,4R)-p-Mentha-1(7),8-dien-2-ol,1TBDMS,isomer #1	C=C(C)C1CCC(=C)C(O[Si](C)(C)C(C)(C)C)C1	1507.2	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 - (2S,4R)-p-Mentha-1(7),8-dien-2-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-9300000000-9db60d2fa688c1c45581	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol GC-MS (1 TMS) - 70eV, Positive	splash10-053i-9310000000-84ca01ad3487a4bae5c3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-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 - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 10V, Positive-QTOF	splash10-0f79-1900000000-0290cf9efbe40492e1d9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 20V, Positive-QTOF	splash10-0f79-7900000000-fde75e8295ad6ee84985	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 40V, Positive-QTOF	splash10-100r-9100000000-af6b6afefd5ebea08bff	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 10V, Negative-QTOF	splash10-0udi-0900000000-ec198c450583dcc0ffae	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 20V, Negative-QTOF	splash10-0udi-0900000000-99ff0708557c327947f6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 40V, Negative-QTOF	splash10-0frl-8900000000-a97018a6ab05ba14ccd3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 10V, Negative-QTOF	splash10-0udi-0900000000-c751b1e6b18ebbd8226b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 20V, Negative-QTOF	splash10-0ue9-0900000000-83706cb4799c27da1464	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 40V, Negative-QTOF	splash10-014i-9600000000-a54de913875752b6ab72	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 10V, Positive-QTOF	splash10-000m-7900000000-e2b5eedaa898fbe3027b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 20V, Positive-QTOF	splash10-002f-9100000000-d4225a2c297184ee4ae3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2S,4R)-p-Mentha-1(7),8-dien-2-ol 40V, Positive-QTOF	splash10-0006-9000000000-0601b4020dca838f45c6	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB021633

KNApSAcK ID

C00056189

Chemspider ID

459675

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

527427

PDB ID

Not Available

ChEBI ID

171972

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (2S,4R)-p-Mentha-1(7),8-dien-2-ol (HMDB0037010)

MOL for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

3D MOL for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

3D SDF for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

3D-SDF for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

PDB for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

3D PDB for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

SMILES for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

INCHI for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

Structure for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

3D Structure for HMDB0037010 ((2S,4R)-p-Mentha-1(7),8-dien-2-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra