Showing Compound Uvaol (FDB013518)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:45 UTC

Update date

2019-11-26 03:08:32 UTC

Primary ID

FDB013518

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Uvaol

Description

Constituent of olive oil and Osmanthus fragrans (sweet osmanthus) Uvaol is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Uvaol exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619)

CAS Number

545-46-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3.beta.)-urs-12-ene-3,28-diol	HMDB
(3beta)-Urs-12-ene-3,28-diol	biospider
Urs-12-ene-3,28-diol	biospider
Urs-12-ene-3beta,28-diol	biospider
Uvaol	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	6.13	ALOGPS
logP	6.11	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	18.95	ChemAxon
pKa (Strongest Basic)	-0.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.76 m³·mol⁻¹	ChemAxon
Polarizability	54.82 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C30H50O2

IUPAC name

8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol

InChI Identifier

InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3

InChI Key

XUARCIYIVXVTAE-UHFFFAOYSA-N

Isomeric SMILES

CC1CCC2(CO)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C

Average Molecular Weight

442.7168

Monoisotopic Molecular Weight

442.381080844

Classification

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 81.39%; H 11.38%; O 7.23%	DFC
Melting Point	Mp 232-233°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +70 (c, 0.93 in CHCl3)	DFC
Spectroscopic UV Data	[neutral] lmax 205 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0000900000-1b790f5e9eb5bf2bf90e	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-1231900000-29ce819c5908fe6bde31	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pvj-7694100000-2b9064a475a1e08a9d51	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-7faf32cca5b2bea1eab2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0001900000-ae3e9b87b7df659c3633	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-1009600000-56d6425409f73e689b7c	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

83774

ChEMBL ID

CHEMBL399873

KEGG Compound ID

Not Available

Pubchem Compound ID

92802

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02391

CRC / DFC (Dictionary of Food Compounds) ID

JFD07-X:JDW15-B

EAFUS ID

Not Available

Dr. Duke ID

UVAOL

BIGG ID

Not Available

KNApSAcK ID

C00032467

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti-proliferative		An agent that inhibits cell growth and division, particularly in cancer cells, preventing tumor expansion. It plays a biological role in regulating cell cycles and has therapeutic applications in cancer treatment, such as chemotherapy and targeted therapy, with key medical uses in managing various types of cancer and other proliferative diseases.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Cytotoxic	52209	An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.	DUKE
Lipoxygenase inhibitor	35856	An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.	DUKE