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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:32:30 UTC

Update Date

2023-02-21 17:25:48 UTC

HMDB ID

HMDB0037302

Secondary Accession Numbers

HMDB37302

Metabolite Identification

Common Name

xi-p-Mentha-3,8-dien-1-ol

Description

xi-p-Mentha-3,8-dien-1-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 xi-p-Mentha-3,8-dien-1-ol.

Structure

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

COMPND    HMDB0037302
HETATM    1  C1  UNL     1      -3.067  -1.629   1.041  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.037  -0.938   0.831  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.934  -0.076  -0.541  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.920  -0.190   0.603  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.146  -0.480   1.466  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.365   0.294   1.265  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.828   0.108  -0.185  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.911   1.088  -0.535  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.288  -1.217  -0.251  1.00  0.00           O  
HETATM   10  C9  UNL     1       0.679   0.297  -1.120  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.513   0.883  -0.338  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.994  -2.408   1.899  1.00  0.00           H  
HETATM   13  H2  UNL     1      -4.031  -1.647   0.615  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.780  -0.701  -0.518  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.905   0.857  -0.039  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.230  -0.380  -1.282  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.031  -1.232   2.219  1.00  0.00           H  
HETATM   18  H7  UNL     1       2.203  -0.053   1.929  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.247   1.364   1.534  1.00  0.00           H  
HETATM   20  H9  UNL     1       3.716   0.550  -1.119  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.349   1.566   0.357  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.557   1.915  -1.186  1.00  0.00           H  
HETATM   23  H12 UNL     1       3.248  -1.270   0.013  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.933   0.947  -1.977  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.312  -0.680  -1.480  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.248   1.235  -1.039  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.155   1.796   0.221  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5    5   11
CONECT    5    6   17
CONECT    6    7   18   19
CONECT    7    8    9   10
CONECT    8   20   21   22
CONECT    9   23
CONECT   10   11   24   25
CONECT   11   26   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

1-methyl-4-(prop-1-en-2-yl)cyclohex-3-en-1-ol

Traditional Name

1-methyl-4-(prop-1-en-2-yl)cyclohex-3-en-1-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H16O/c1-8(2)9-4-6-10(3,11)7-5-9/h4,11H,1,5-7H2,2-3H3

InChI Key

ZAGYKNAXCCJVSM-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
Tertiary 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: HMDB0037302)

Source

Endogenous

Endogenous (HMDB: HMDB0037302)

Plant

Plant (HMDB: HMDB0037302)

Animal

Animal (HMDB: HMDB0037302)

Exogenous

Food

Food (HMDB: HMDB0037302)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0037302)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037302)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037302)

Lipid metabolism pathway (HMDB: HMDB0037302)

Cellular process

Cell signaling (HMDB: HMDB0037302)

Biochemical process

Lipid transport (HMDB: HMDB0037302)

Role

Biological role

Energy source (HMDB: HMDB0037302)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037302)

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	2.36 g/L	ALOGPS
logP	2.48	ALOGPS
logP	1.83	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	18.94	ChemAxon
pKa (Strongest Basic)	-1.1	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	48.24 m³·mol⁻¹	ChemAxon
Polarizability	18.22 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]+	136.487	31661259
DarkChem	[M-H]-	131.77	31661259
DeepCCS	[M+H]+	137.419	30932474
DeepCCS	[M-H]-	133.985	30932474
DeepCCS	[M-2H]-	171.147	30932474
DeepCCS	[M+Na]+	146.685	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	138.0	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	137.8	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
xi-p-Mentha-3,8-dien-1-ol	CC(=C)C1=CCC(C)(O)CC1	1663.7	Standard polar	33892256
xi-p-Mentha-3,8-dien-1-ol	CC(=C)C1=CCC(C)(O)CC1	1168.8	Standard non polar	33892256
xi-p-Mentha-3,8-dien-1-ol	CC(=C)C1=CCC(C)(O)CC1	1173.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
xi-p-Mentha-3,8-dien-1-ol,1TMS,isomer #1	C=C(C)C1=CCC(C)(O[Si](C)(C)C)CC1	1385.4	Semi standard non polar	33892256
xi-p-Mentha-3,8-dien-1-ol,1TBDMS,isomer #1	C=C(C)C1=CCC(C)(O[Si](C)(C)C(C)(C)C)CC1	1641.1	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 - xi-p-Mentha-3,8-dien-1-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-b96993e982e063a5b635	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - xi-p-Mentha-3,8-dien-1-ol GC-MS (1 TMS) - 70eV, Positive	splash10-0adu-9420000000-e8c9cb98fe5340990088	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - xi-p-Mentha-3,8-dien-1-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - xi-p-Mentha-3,8-dien-1-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 - xi-p-Mentha-3,8-dien-1-ol 10V, Positive-QTOF	splash10-0f79-0900000000-9e4f28f07514beb87475	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 20V, Positive-QTOF	splash10-0f79-4900000000-f6501a576ce473a03ac1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 40V, Positive-QTOF	splash10-0ldi-9400000000-1590b0011ef7587a7acc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 10V, Negative-QTOF	splash10-0udi-0900000000-a77a4a0ad0a7ea75010b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 20V, Negative-QTOF	splash10-0udi-0900000000-1d7fa3041815b936bc5a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 40V, Negative-QTOF	splash10-0k9l-4900000000-765a0f4b800051e20a4f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 20V, Negative-QTOF	splash10-0ue9-1900000000-83a32e33e6a57fab2a47	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 40V, Negative-QTOF	splash10-014i-9300000000-f7e8cc097b501a0aa8a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 10V, Positive-QTOF	splash10-000i-5900000000-ca25f745a620a34c8e05	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 20V, Positive-QTOF	splash10-004l-9100000000-4123ebe4f92c0b44014f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-p-Mentha-3,8-dien-1-ol 40V, Positive-QTOF	splash10-00or-9000000000-854b8a21b6fc820e87b0	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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+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

Cytoplasm
Extracellular
Membrane

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

FDB016321

KNApSAcK ID

Not Available

Chemspider ID

35014398

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78385250

PDB ID

Not Available

ChEBI ID

171947

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 xi-p-Mentha-3,8-dien-1-ol (HMDB0037302)

MOL for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

3D MOL for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

3D SDF for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

3D-SDF for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

PDB for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

3D PDB for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

SMILES for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

INCHI for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

Structure for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

3D Structure for HMDB0037302 (xi-p-Mentha-3,8-dien-1-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra