MiMeDB: Showing metabocard for Perilla alcohol (MMDBc0047743)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:40:36 UTC

Update Date

2022-09-01 01:47:56 UTC

MiMeDB ID

MMDBc0047743

Metabolite Identification

Common Name

Perilla 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

Synonyms

Not Available

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

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0006-9600000000-852faf99c20eb91e9836	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00mo-9200000000-6d3cda5b991dc6f0a098	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9300000000-f32f7e87d33288c8045d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0006-9600000000-852faf99c20eb91e9836	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007x-9400000000-0642824f11b9c7fd315d	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05gu-9510000000-9f19c403be332e74c8ad	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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00du-3900000000-a6c07543feea874fe65d	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004u-9000000000-352e042e70150a70fc17	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0bvj-9000000000-9a2da0a6d60335f43f46	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-00mo-9200000000-81544f3016fa24bad81f	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-1900000000-2f012741782fc72aa3df	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-5900000000-849092ef4eeddd440687	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gc0-9200000000-fd4b15fd9437d4b70409	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-20d0d9f448f90e31136f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uk9-0900000000-a390120b9758e2ca2f5d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4900000000-39d18f7a3231672157f5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-8fa95dbd5fa627e933fa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9200000000-7da801ed46abad2dd628	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f84-9800000000-bd8e7097a31172f8ad0e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9200000000-373d4892dedc5ff6266f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mo-9000000000-a6d86d2ceee0f1021fd3	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Pancreas
Prostate

Tissue Locations

Pancreas
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

#<MetaboliteProteinLink:0x000055b76dca1d20>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	1	Human Feces	Unknown
NULL	Proteobacteria	1
	Firmicutes	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details
Plant	Leaves	Mentha spicata	FooDB	31437929	details
Plant	Fruit	Rubus	FooDB	31437929	details
Plant	Leaves	Laurus nobilis	FooDB	31437929	details
Plant	Plant	Matricaria recutita	FooDB	31437929	details
Plant	Juice	Rubus	FooDB	31437929	details
Plant	Essential oil	Carum carvi	FooDB	31437929	details
Plant	Plant	Carum carvi	FooDB	31437929	details
Plant	Rhizome	Zingiber officinale	FooDB	31437929	details
Plant	Plant	Satureja montana	FooDB	31437929	details
Plant	Essential oil	Mentha spicata	FooDB	31437929	details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB		details
Human	Detected and Quantified	0.028	0.023	0.032	Adult (>18 years old)	Female	Perillyl alcohol administration for cancer treatment	HMDB	10379660	details
Human Pancreas	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597	details

External Links

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1093/carcin/18.8.1655. [PubMed:9276644 ]
Belanger JT: Perillyl alcohol: applications in oncology. Altern Med Rev. 1998 Dec;3(6):448-57. [PubMed:9855569 ]
Greenwald P, Milner JA, Anderson DE, McDonald SS: Micronutrients in cancer chemoprevention. Cancer Metastasis Rev. 2002;21(3-4):217-30. doi: 10.1023/a:1021202709003. [PubMed:12549762 ]

Showing metabocard for Perilla alcohol (MMDBc0047743)

MOL for #<Metabolite:0x000055b76dea7228>

3D MOL for #<Metabolite:0x000055b76dea7228>

3D SDF for #<Metabolite:0x000055b76dea7228>

3D-SDF for #<Metabolite:0x000055b76dea7228>

PDB for #<Metabolite:0x000055b76dea7228>

3D PDB for #<Metabolite:0x000055b76dea7228>

SMILES for #<Metabolite:0x000055b76dea7228>

INCHI for #<Metabolite:0x000055b76dea7228>

Structure for #<Metabolite:0x000055b76dea7228>

3D Structure for #<Metabolite:0x000055b76dea7228>