Metabolite Perillyl alcohol

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

Similar Structures

Synonyms

Not Available

UNII

319R5C7293

CAS number

536-59-4

Weight

Average: 152.237
Monoisotopic: 152.120115135

Chemical Formula

C₁₀H₁₆O

InChI Key

NDTYTMIUWGWIMO-UHFFFAOYSA-N

InChI

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

IUPAC Name

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

SMILES

CC(=C)C1CCC(CO)=CC1

Reactions

(4R)-limonene

Perillyl alcohol
- Perillyl alcohol
  
  Perillyl acid

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-MS (1 TMS)	GC-MS	splash10-0006-9600000000-852faf99c20eb91e9836
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-007x-9400000000-0642824f11b9c7fd315d
GC-MS Spectrum - EI-B	GC-MS	splash10-00mo-9200000000-6d3cda5b991dc6f0a098
GC-MS Spectrum - EI-B	GC-MS	splash10-014l-9300000000-f32f7e87d33288c8045d
GC-MS Spectrum - GC-MS	GC-MS	splash10-0006-9600000000-852faf99c20eb91e9836
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	LC-MS/MS	splash10-00du-3900000000-a6c07543feea874fe65d
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	LC-MS/MS	splash10-004u-9000000000-352e042e70150a70fc17
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	LC-MS/MS	splash10-0bvj-9000000000-9a2da0a6d60335f43f46
MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	LC-MS/MS	splash10-00mo-9200000000-81544f3016fa24bad81f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-9300000000-eb889423e86321568222
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-0900000000-15011199bd68c8f3930d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-9100000000-6303bb26afc061d39bc7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-0900000000-e3073b982f99567a840a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0uxr-9200000000-0f5d4402b5cbf58f7697
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0036-9000000000-ce79a1145ad031b9e6ad
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	138.0383868	predicted	DarkChem Lite v0.1.0
[M-H]-	137.96877	predicted	DeepCCS 1.0 (2019)
[M+H]+	138.2401868	predicted	DarkChem Lite v0.1.0
[M+H]+	141.45284	predicted	DeepCCS 1.0 (2019)
[M+Na]+	138.0585868	predicted	DarkChem Lite v0.1.0
[M+Na]+	150.6616	predicted	DeepCCS 1.0 (2019)

External Links

Human Metabolome Database: HMDB0003634
ChemSpider: 10362
BindingDB: 50252404
ChEBI: 15420
ChEMBL: CHEMBL444711
Wikipedia: Perillyl_alcohol

Predicted Properties

Property	Value	Source
Water Solubility	1.9 mg/mL	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	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Metabolite Perillyl alcohol

Structure for Perillyl alcohol

Collision Cross Sections (CCS)