MiMeDB: Showing metabocard for P-Menth-1-en-9-ol (MMDBc0047738)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:40:23 UTC

Update Date

2024-04-30 20:29:15 UTC

Metabolite ID

MMDBc0047738

Metabolite Identification

Common Name

P-Menth-1-en-9-ol

Description

p-Menth-1-en-9-ol is found in bilberry. p-Menth-1-en-9-ol is a constituent of Vaccinium myrtillus (bilberry) and tangerine oil.

Structure

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

HMDB0037007
     RDKit          3D
p-Menth-1-en-9-ol
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.2035    0.9133   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1312    0.0470   -0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.2142    0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791   -0.7110    1.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   -0.8765    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    0.0905    0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436    1.5236    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8427   -0.1235   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942    0.0053   -1.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254   -0.9107   -0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -1.0699   -1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1732    0.4374   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719    0.9918   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.9177   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464    1.0177    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -1.6967    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -0.3740    2.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -1.9065    0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804   -0.1199    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    2.1063    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154    1.9316   -0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3039    1.7751    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785    0.5441    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759   -1.1799   -0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3746    0.3285   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959    0.0189   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.7575   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -1.1298   -2.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -2.0071   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

HMDB0037007
     RDKit          3D
p-Menth-1-en-9-ol
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.2035    0.9133   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1312    0.0470   -0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.2142    0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791   -0.7110    1.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   -0.8765    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    0.0905    0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436    1.5236    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8427   -0.1235   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942    0.0053   -1.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254   -0.9107   -0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -1.0699   -1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1732    0.4374   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719    0.9918   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.9177   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464    1.0177    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -1.6967    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -0.3740    2.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -1.9065    0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804   -0.1199    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    2.1063    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154    1.9316   -0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3039    1.7751    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785    0.5441    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759   -1.1799   -0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3746    0.3285   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959    0.0189   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.7575   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -1.1298   -2.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -2.0071   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

COMPND    HMDB0037007
HETATM    1  C1  UNL     1       3.204   0.913  -0.799  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.131   0.047  -0.237  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.643   0.214   0.996  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.579  -0.711   1.443  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.521  -0.876   0.421  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.622   0.090   0.711  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.244   1.524   0.672  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.843  -0.123  -0.151  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.594   0.005  -1.511  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.025  -0.911  -0.980  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.511  -1.070  -1.008  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.173   0.437  -0.551  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.072   0.992  -1.905  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.118   1.918  -0.316  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.046   1.018   1.613  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.082  -1.697   1.636  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.108  -0.374   2.399  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.946  -1.906   0.627  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.980  -0.120   1.771  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.044   2.106   1.203  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.215   1.932  -0.358  1.00  0.00           H  
HETATM   22  H11 UNL     1      -0.304   1.775   1.178  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.678   0.544   0.133  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.176  -1.180  -0.003  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.375   0.329  -1.999  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.296   0.019  -1.561  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.402  -1.758  -1.588  1.00  0.00           H  
HETATM   28  H17 UNL     1       1.861  -1.130  -2.035  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.737  -2.007  -0.463  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   23   24
CONECT    9   25
CONECT   10   11   26   27
CONECT   11   28   29
END

HMDB0037007
     RDKit          3D
p-Menth-1-en-9-ol
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.2035    0.9133   -0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1312    0.0470   -0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431    0.2142    0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791   -0.7110    1.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215   -0.8765    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6222    0.0905    0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2436    1.5236    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8427   -0.1235   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5942    0.0053   -1.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0254   -0.9107   -0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5108   -1.0699   -1.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1732    0.4374   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0719    0.9918   -1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.9177   -0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464    1.0177    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0822   -1.6967    1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -0.3740    2.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9459   -1.9065    0.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804   -0.1199    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0443    2.1063    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154    1.9316   -0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3039    1.7751    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785    0.5441    0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759   -1.1799   -0.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3746    0.3285   -1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2959    0.0189   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -1.7575   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -1.1298   -2.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -2.0071   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  5 10  1  0
 10 11  1  0
 11  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

Synonyms

Value	Source
(+)-P-Menth-1-en-9-ol,mixture OF isomers	HMDB
(+)-P-Mentha-1-en-9-ol	HMDB
(4R,8R)-(+)-P-Menth-1-en-9-ol	HMDB
(4R,8S)-(+)-P-Menth-1-en-9-ol	HMDB
2-(4-Methyl-3-cyclohexen-1-yl)-1-propanol	HMDB
2-(4-Methyl-3-cycohexen-1-yl)-1-propanol	HMDB
b,4-Dimethyl-3-cyclohexene-1-ethanol, 9ci	HMDB
beta,4-Dimethyl-(R-(r,r))-3-cyclohexene-1-ethanol	HMDB
beta,4-Dimethyl-3-cyclohexene-1-ethanol	HMDB
beta,4-Dimethylcyclohex-3-ene-1-ethanol	HMDB
Menth-1-en-9-ol	HMDB
P-Menth-1-ene-9-ol	HMDB
P-Mentha-1-en-9-ol	HMDB

Molecular Formula

C₁₀H₁₈O

Average Mass

154.2493

Monoisotopic Mass

154.135765198

IUPAC Name

2-(4-methylcyclohex-3-en-1-yl)propan-1-ol

Traditional Name

2-(4-methylcyclohex-3-en-1-yl)propan-1-ol

CAS Registry Number

Not Available

SMILES

CC(CO)C1CCC(C)=CC1

InChI Identifier

InChI=1S/C10H18O/c1-8-3-5-10(6-4-8)9(2)7-11/h3,9-11H,4-7H2,1-2H3

InChI Key

ZTYHGIAOVUPAAH-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
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.3 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.21	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	17.75	ChemAxon
pKa (Strongest Basic)	-1.6	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	2	ChemAxon
Refractivity	48.55 m³·mol⁻¹	ChemAxon
Polarizability	19.22 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9400000000-53438408024a3caa6fd9	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0h90-9520000000-ac53bc0838aaef4f2580	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-1900000000-45b1a7e5543b3891d9f0	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-8900000000-a9ac25a82d63df629860	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldj-9200000000-6d0d48538d0035f5e7ae	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-662fd7167387c4bcefc3	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uk9-0900000000-34884b5761200f0d105d	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-8900000000-dcc04fa637d169e52ff4	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-8900000000-3e3aa0ed07e91240a750	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0005-9200000000-017e94914fdb83292cf2	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-b8ac29077ccee09c4278	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uk9-0900000000-243df604faf48a2e8609	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-afb393f52db985e227d7	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-1900000000-97ecb1c861bc888c1e0b	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Fruit	Vaccinium myrtillus	FooDB	31437929
Plant	Essential oil	Citrus limon	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0037007

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015982

KNApSAcK ID

C00010933

Chemspider ID

78253

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86753

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. 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). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. 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 P-Menth-1-en-9-ol (MMDBc0047738)

MOL for #<Metabolite:0x00007fecab0e59a8>

3D MOL for #<Metabolite:0x00007fecab0e59a8>

3D SDF for #<Metabolite:0x00007fecab0e59a8>

3D-SDF for #<Metabolite:0x00007fecab0e59a8>

PDB for #<Metabolite:0x00007fecab0e59a8>

3D PDB for #<Metabolite:0x00007fecab0e59a8>

SMILES for #<Metabolite:0x00007fecab0e59a8>

INCHI for #<Metabolite:0x00007fecab0e59a8>

Structure for #<Metabolite:0x00007fecab0e59a8>

3D Structure for #<Metabolite:0x00007fecab0e59a8>