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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 02:18:06 UTC

Update Date

2023-02-21 17:16:45 UTC

HMDB ID

HMDB0003634

Secondary Accession Numbers

HMDB03634

Metabolite Identification

Common Name

Perillyl alcohol

Description

Perillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID:9855569 ).

Structure

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

COMPND    HMDB0003634
HETATM    1  C1  UNL     1      -2.850  -1.372  -0.214  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.275  -0.230   0.150  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.219   0.932   0.368  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.812  -0.067   0.338  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.117  -1.390   0.160  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.364  -1.242   0.225  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.926  -0.104  -0.153  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.407  -0.014  -0.067  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.737   1.045   0.810  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.195   1.071  -0.650  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.288   0.990  -0.592  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.312  -2.298  -0.408  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.928  -1.466  -0.347  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.696   1.884   0.413  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.746   0.709   1.324  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.949   0.999  -0.485  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.647   0.263   1.388  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.407  -1.813  -0.815  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.417  -2.088   0.961  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.940  -2.064   0.576  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.867   0.157  -1.062  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.866  -0.926   0.342  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.709   0.941   0.986  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.605   1.971  -0.103  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.478   1.269  -1.725  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.665   1.973  -0.218  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.765   0.869  -1.608  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    7   20
CONECT    7    8   10
CONECT    8    9   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

Value	Source
1-Hydroxymethyl-4-isopropenyl-1-cyclohexene	ChEBI
1-Perillalcohol	ChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-methanol	ChEBI
4-Isopropenyl-1-cyclohexene carbinol	ChEBI
4-Isopropenylcyclohex-1-en-1-ylmethanol	ChEBI
Dihydrocuminyl alcoholn	ChEBI
Isocarveol	ChEBI
p-Mentha-1,8-dien-7-ol	ChEBI
Perilla alcohol	ChEBI
Perillol	ChEBI
(-)-Perillyl alcohol	HMDB
(S)-(-)-Perillyl alcohol	HMDB
1,8-p-Menthadien-7-ol	HMDB
4-Isopropenyl-cyclohex-1-ene-1-methanol	HMDB
Dihydrocuminic alcohol	HMDB
Dihydrocuminyl alcohol	HMDB
Hydrocumin alcohol	HMDB
Iso-carveol	HMDB
Para-mentha-1,8-dien-7-ol	HMDB
Perill alcohol	HMDB
Perillic alcohol	HMDB
Cyclohex-1-ene-1-methanol, 4(1-methylethenyl)	HMDB
Perilla alcohol, (S)-isomer	HMDB
Perilla alcohol, (R)-isomer	HMDB
(-)-p-Mentha-1,8-dien-7-ol	HMDB
(S)-Perillyl alcohol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.237

Monoisotopic Molecular Weight

152.120115135

IUPAC Name

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

Traditional Name

(-)-perillylalcohol

CAS Registry Number

536-59-4

SMILES

CC(=C)C1CCC(CO)=CC1

InChI Identifier

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

InChI Key

NDTYTMIUWGWIMO-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

limonene monoterpenoid (CHEBI:15420 )
perillyl alcohol (CPD-261 )

Ontology

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10379660)

Cellular substructure

Organ

Pancreas (HMDB: HMDB0003634)
Prostate (HMDB: HMDB0003634)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003634)

Source

Exogenous

Exogenous (HMDB: HMDB0003634)

Food

Food (HMDB: HMDB0003634)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)
Caraway (FooDB: FOOD00043)

Herb

Fruit

Berry

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

Endogenous

Plant

Plant (HMDB: HMDB0003634)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0003634)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0003634)

Lipid metabolism pathway (HMDB: HMDB0003634)

Cellular process

Cell signaling (HMDB: HMDB0003634)

Biochemical process

Lipid transport (HMDB: HMDB0003634)

Role

Industrial applicationBiological role

Modulator

Apoptotic (HMDB: HMDB0003634)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	244 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.17	GRIFFIN,S ET AL. (1999)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.9 g/L	ALOGPS
logP	2.5	ALOGPS
logP	1.94	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	16.86	ChemAxon
pKa (Strongest Basic)	-2	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	48.26 m³·mol⁻¹	ChemAxon
Polarizability	18.19 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]+	134.831	31661259
DarkChem	[M-H]-	131.468	31661259
DeepCCS	[M+H]+	141.453	30932474
DeepCCS	[M-H]-	137.969	30932474
DeepCCS	[M-2H]-	175.177	30932474
DeepCCS	[M+Na]+	150.662	30932474
AllCCS	[M+H]+	133.8	32859911
AllCCS	[M+H-H2O]+	129.3	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.1	32859911
AllCCS	[M-H]-	137.5	32859911
AllCCS	[M+Na-2H]-	139.0	32859911
AllCCS	[M+HCOO]-	140.8	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.	4.41 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7119 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1819.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	401.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	221.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	436.7 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	536.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1041.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	355.6 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	1119.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	344.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	408.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	410.5 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	41.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Perillyl alcohol	CC(=C)C1CCC(CO)=CC1	2006.9	Standard polar	33892256
Perillyl alcohol	CC(=C)C1CCC(CO)=CC1	1270.3	Standard non polar	33892256
Perillyl alcohol	CC(=C)C1CCC(CO)=CC1	1288.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Perillyl alcohol,1TMS,isomer #1	C=C(C)C1CC=C(CO[Si](C)(C)C)CC1	1351.4	Semi standard non polar	33892256
Perillyl alcohol,1TBDMS,isomer #1	C=C(C)C1CC=C(CO[Si](C)(C)C(C)(C)C)CC1	1584.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Perillyl alcohol GC-MS (1 TMS)	splash10-0006-9600000000-852faf99c20eb91e9836	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Perillyl alcohol EI-B (Non-derivatized)	splash10-00mo-9200000000-6d3cda5b991dc6f0a098	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Perillyl alcohol EI-B (Non-derivatized)	splash10-014l-9300000000-f32f7e87d33288c8045d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Perillyl alcohol GC-MS (Non-derivatized)	splash10-0006-9600000000-852faf99c20eb91e9836	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perillyl alcohol GC-MS (Non-derivatized) - 70eV, Positive	splash10-007x-9400000000-0642824f11b9c7fd315d	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perillyl alcohol GC-MS (1 TMS) - 70eV, Positive	splash10-05gu-9510000000-9f19c403be332e74c8ad	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Perillyl alcohol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00du-3900000000-a6c07543feea874fe65d	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-004u-9000000000-352e042e70150a70fc17	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Perillyl alcohol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0bvj-9000000000-9a2da0a6d60335f43f46	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Perillyl alcohol EI-B (HITACHI M-80B) , Positive-QTOF	splash10-00mo-9200000000-81544f3016fa24bad81f	2012-08-31	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Positive-QTOF	splash10-0udr-1900000000-2f012741782fc72aa3df	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Positive-QTOF	splash10-000i-5900000000-849092ef4eeddd440687	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Positive-QTOF	splash10-0gc0-9200000000-fd4b15fd9437d4b70409	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Negative-QTOF	splash10-0udi-0900000000-20d0d9f448f90e31136f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Negative-QTOF	splash10-0uk9-0900000000-a390120b9758e2ca2f5d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Negative-QTOF	splash10-00di-4900000000-39d18f7a3231672157f5	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Negative-QTOF	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Negative-QTOF	splash10-001i-0900000000-8fa95dbd5fa627e933fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Negative-QTOF	splash10-014i-9200000000-7da801ed46abad2dd628	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 10V, Positive-QTOF	splash10-0f84-9800000000-bd8e7097a31172f8ad0e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 20V, Positive-QTOF	splash10-0006-9200000000-373d4892dedc5ff6266f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Perillyl alcohol 40V, Positive-QTOF	splash10-00mo-9000000000-a6d86d2ceee0f1021fd3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Pancreas
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.028 (0.023 - 0.032) uM	Adult (>18 years old)	Female	Perillyl alcohol administration for cancer treatment	10379660	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Perillyl alcohol administration for cancer treatment
Zhang Z, Chen H, Chan KK, Budd T, Ganapathi R: Gas chromatographic-mass spectrometric analysis of perillyl alcohol and metabolites in plasma. J Chromatogr B Biomed Sci Appl. 1999 May 14;728(1):85-95. [PubMed:10379660 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014923

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15420

Food Biomarker Ontology

Not Available

VMH ID

PERILLYL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Li, Qian-he; Zhan, Xiao-xiong; Feng, Zhen-zhen; Li, Xue-hui; Wang, Le-fu. Synthesis of perillyl alcohol via liquid phase rearrangement of 2,10-epoxypinane catalyzed by morpholinium nitrate. Hunan Shifan Daxue Ziran Kexue Xuebao (2006), 29(1), 56-59.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30. [PubMed:12549762 ]
Stayrook KR, McKinzie JH, Burke YD, Burke YA, Crowell PL: Induction of the apoptosis-promoting protein Bak by perillyl alcohol in pancreatic ductal adenocarcinoma relative to untransformed ductal epithelial cells. Carcinogenesis. 1997 Aug;18(8):1655-8. [PubMed:9276644 ]
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Enzymes

Enzyme Details

1. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Showing metabocard for Perillyl alcohol (HMDB0003634)

MOL for HMDB0003634 (Perillyl alcohol)

3D MOL for HMDB0003634 (Perillyl alcohol)

3D SDF for HMDB0003634 (Perillyl alcohol)

3D-SDF for HMDB0003634 (Perillyl alcohol)

PDB for HMDB0003634 (Perillyl alcohol)

3D PDB for HMDB0003634 (Perillyl alcohol)

SMILES for HMDB0003634 (Perillyl alcohol)

INCHI for HMDB0003634 (Perillyl alcohol)

Structure for HMDB0003634 (Perillyl alcohol)

3D Structure for HMDB0003634 (Perillyl alcohol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes