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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:14:56 UTC

Update Date

2022-03-07 02:55:09 UTC

HMDB ID

HMDB0037006

Secondary Accession Numbers

HMDB37006

Metabolite Identification

Common Name

cis-Isopulegone

Description

cis-Isopulegone 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 significant number of articles have been published on cis-Isopulegone.

Structure

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

HMDB0037006
     RDKit          3D
cis-Isopulegone
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.4479   -0.2756    0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0275    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158    0.9296   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -0.5188    0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    0.6117    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2766    0.4918    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382    0.1051   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1492    0.0366   -0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7057    1.2713   -0.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -1.2982   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081   -1.3162   -0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786   -0.9378    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3818    0.1283    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906    1.9363   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    0.5126   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4151    1.0991   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -1.2171    1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    1.5863    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4471    0.7910    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207    1.4955    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876   -0.2695    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863    0.7807   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4018   -0.1821   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.7399    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2054    1.9374   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -1.9222    0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -1.6765   -1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -2.3970   -0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7813   -0.9897   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 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

HMDB0037006
     RDKit          3D
cis-Isopulegone
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.4479   -0.2756    0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0275    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158    0.9296   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -0.5188    0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    0.6117    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2766    0.4918    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382    0.1051   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1492    0.0366   -0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7057    1.2713   -0.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -1.2982   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081   -1.3162   -0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786   -0.9378    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3818    0.1283    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906    1.9363   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    0.5126   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4151    1.0991   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -1.2171    1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    1.5863    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4471    0.7910    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207    1.4955    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876   -0.2695    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863    0.7807   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4018   -0.1821   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.7399    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2054    1.9374   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -1.9222    0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -1.6765   -1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -2.3970   -0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7813   -0.9897   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 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    HMDB0037006
HETATM    1  C1  UNL     1       3.448  -0.276   0.819  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.330   0.027   0.185  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.416   0.930  -1.001  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.994  -0.519   0.638  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.206   0.612   1.138  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.277   0.492   1.050  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.638   0.105  -0.366  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.149   0.037  -0.499  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.706   1.271  -0.204  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.087  -1.298  -0.537  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.408  -1.316  -0.480  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.379  -0.938   1.688  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.382   0.128   0.473  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.791   1.936  -0.686  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.137   0.513  -1.721  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.415   1.099  -1.444  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.224  -1.217   1.468  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.486   1.586   0.641  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.447   0.791   2.226  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.721   1.495   1.229  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.688  -0.270   1.741  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.186   0.781  -1.093  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.402  -0.182  -1.569  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.572  -0.740   0.164  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.205   1.937  -0.772  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.483  -1.922   0.273  1.00  0.00           H  
HETATM   27  H16 UNL     1      -1.447  -1.677  -1.490  1.00  0.00           H  
HETATM   28  H17 UNL     1       0.718  -2.397  -0.398  1.00  0.00           H  
HETATM   29  H18 UNL     1       0.781  -0.990  -1.473  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   10   22
CONECT    8    9   23   24
CONECT    9   25
CONECT   10   11   26   27
CONECT   11   28   29
END

HMDB0037006
     RDKit          3D
cis-Isopulegone
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.4479   -0.2756    0.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301    0.0275    0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158    0.9296   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -0.5188    0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    0.6117    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2766    0.4918    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6382    0.1051   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1492    0.0366   -0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7057    1.2713   -0.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -1.2982   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081   -1.3162   -0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3786   -0.9378    1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3818    0.1283    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906    1.9363   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368    0.5126   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4151    1.0991   -1.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -1.2171    1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    1.5863    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4471    0.7910    2.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7207    1.4955    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6876   -0.2695    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863    0.7807   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4018   -0.1821   -1.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725   -0.7399    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2054    1.9374   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -1.9222    0.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -1.6765   -1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7181   -2.3970   -0.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7813   -0.9897   -1.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 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

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pulegone, (S)-isomer	MeSH
Isopulegone	MeSH
Pulegone, (R)-isomer	MeSH
Pulegone	MeSH
cis-P-Menth-8-en-7-ol	HMDB
cis-Isopulegone	MeSH

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.253

Monoisotopic Molecular Weight

154.1357652

IUPAC Name

[4-(prop-1-en-2-yl)cyclohexyl]methanol

Traditional Name

[4-(prop-1-en-2-yl)cyclohexyl]methanol

CAS Registry Number

22521-57-9

SMILES

CC(=C)C1CCC(CO)CC1

InChI Identifier

InChI=1S/C10H18O/c1-8(2)10-5-3-9(7-11)4-6-10/h9-11H,1,3-7H2,2H3

InChI Key

GMYHXOPIKMGWOM-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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037006)

Source

Endogenous

Endogenous (HMDB: HMDB0037006)

Animal

Animal (HMDB: HMDB0037006)

Exogenous

Food

Food (HMDB: HMDB0037006)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0037006)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037006)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037006)

Lipid metabolism pathway (HMDB: HMDB0037006)

Cellular process

Cell signaling (HMDB: HMDB0037006)

Biochemical process

Lipid transport (HMDB: HMDB0037006)

Role

Biological role

Energy source (HMDB: HMDB0037006)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037006)

Physical Properties

State

Solid

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	0.68 g/L	ALOGPS
logP	2.88	ALOGPS
logP	2.27	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	17.64	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	47.48 m³·mol⁻¹	ChemAxon
Polarizability	19.18 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]+	135.525	31661259
DarkChem	[M-H]-	131.675	31661259
DeepCCS	[M+H]+	142.532	30932474
DeepCCS	[M-H]-	138.781	30932474
DeepCCS	[M-2H]-	176.05	30932474
DeepCCS	[M+Na]+	151.588	30932474
AllCCS	[M+H]+	134.9	32859911
AllCCS	[M+H-H2O]+	130.6	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	139.3	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	142.8	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.	4.2 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3636 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.46 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1965.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	431.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	222.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	325.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	502.6 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	573.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	107.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1052.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	385.1 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	1244.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	382.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	382.9 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	50.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-Isopulegone	CC(=C)C1CCC(CO)CC1	1937.8	Standard polar	33892256
cis-Isopulegone	CC(=C)C1CCC(CO)CC1	1274.7	Standard non polar	33892256
cis-Isopulegone	CC(=C)C1CCC(CO)CC1	1276.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-Isopulegone,1TMS,isomer #1	C=C(C)C1CCC(CO[Si](C)(C)C)CC1	1355.8	Semi standard non polar	33892256
cis-Isopulegone,1TBDMS,isomer #1	C=C(C)C1CCC(CO[Si](C)(C)C(C)(C)C)CC1	1582.7	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 - cis-Isopulegone GC-MS (Non-derivatized) - 70eV, Positive	splash10-007o-9400000000-a247cbbec335523ba1e7	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-Isopulegone GC-MS (1 TMS) - 70eV, Positive	splash10-0233-9520000000-06131451c365b8804034	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-Isopulegone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-Isopulegone 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 - cis-Isopulegone 10V, Positive-QTOF	splash10-0a4r-1900000000-ebc318e6ea2296e9b243	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 20V, Positive-QTOF	splash10-000i-6900000000-d0fba3ca8ecb10c7881a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 40V, Positive-QTOF	splash10-0le9-9100000000-89c320d399fadd3a5f65	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 10V, Negative-QTOF	splash10-0udi-0900000000-6bcb61d47c03f19f1f84	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 20V, Negative-QTOF	splash10-0uk9-0900000000-bb63b13add45f9effd8e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 40V, Negative-QTOF	splash10-00di-4900000000-eabe6ebf22aa7253a752	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 10V, Positive-QTOF	splash10-000t-9600000000-4776300854fe5e5a846b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 20V, Positive-QTOF	splash10-001m-9200000000-1434970da9f01c74862b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 40V, Positive-QTOF	splash10-017l-9000000000-344f5207cc665287b547	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 10V, Negative-QTOF	splash10-0udi-0900000000-f2fbae7832587715e966	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 20V, Negative-QTOF	splash10-0f79-0900000000-f7cc0a02a4fb771b64bf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Isopulegone 40V, Negative-QTOF	splash10-060u-9700000000-4956a04435b33f76cf19	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB015981

KNApSAcK ID

C00000820

Chemspider ID

453538

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

519954

PDB ID

Not Available

ChEBI ID

Not Available

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 cis-Isopulegone (HMDB0037006)

MOL for HMDB0037006 (cis-Isopulegone)

3D MOL for HMDB0037006 (cis-Isopulegone)

3D SDF for HMDB0037006 (cis-Isopulegone)

3D-SDF for HMDB0037006 (cis-Isopulegone)

PDB for HMDB0037006 (cis-Isopulegone)

3D PDB for HMDB0037006 (cis-Isopulegone)

SMILES for HMDB0037006 (cis-Isopulegone)

INCHI for HMDB0037006 (cis-Isopulegone)

Structure for HMDB0037006 (cis-Isopulegone)

3D Structure for HMDB0037006 (cis-Isopulegone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra