Showing Compound Betulin (FDB015789)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:03 UTC

Update date

2025-11-19 00:59:27 UTC

Primary ID

FDB015789

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Betulin

Description

Constituent of Corylus avellana (filbert) and Vicia faba Betulin (lup-20(29)-ene-3?,28-diol) is an abundant naturally occurring triterpene. It is commonly isolated from the bark of birch trees and forms up to 30% of the dry weight of the extractive. The purpose of the compound in the bark is not known. It can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself.; Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28. Betulin is found in many foods, some of which are common walnut, common sage, nuts, and common hazelnut.

CAS Number

473-98-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(3beta)-Lup-20(29)-ene-3,28-diol	HMDB
Betulenol	HMDB
Betuline	HMDB
Betulinic alcohol	HMDB
Betulinol	HMDB
Betulinol (obsol.)	HMDB
Betulol	HMDB
Lup-20(29)-ene-3 beta,28-diol	HMDB
Lup-20(29)-ene-3beta ,28-diol	HMDB
Lup-20(29)-ene-3beta,28-diol	HMDB
Lup-20(30)-ene-3beta ,28-diol	HMDB
Lup-20(30)-ene-3beta,28-diol	HMDB
Messagenin	HMDB
Trochol	HMDB
Betulin	db_source
Lup-20(29)-ene-3,28-diol, (3β)-	biospider
Lup-20(29)-ene-3,28-diol, (3beta)-	biospider
Lup-20(29)-ene-3β,28-diol	biospider
Lup-20(30)-ene-3β,28-diol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.00032 g/L	ALOGPS
logP	5.34	ALOGPS
logP	6.17	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	18.85	ChemAxon
pKa (Strongest Basic)	-0.65	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	2	ChemAxon
Refractivity	132.68 m³·mol⁻¹	ChemAxon
Polarizability	54.76 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

5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-ol

InChI Identifier

InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3

InChI Key

FVWJYYTZTCVBKE-UHFFFAOYSA-N

Isomeric SMILES

CC(=C)C1CCC2(CO)CCC3(C)C(CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C12

Average Molecular Weight

442.7168

Monoisotopic Molecular Weight

442.381080844

Classification

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Cadinane sesquiterpenoid
Sesquiterpenoid
Tetralin
Quinone
Aryl alkyl ketone
Aryl ketone
Aryl-aldehyde
Vinylogous acid
Ketone
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aldehyde
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Plant:

Fabaceae

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Pharmaceutical industry:

Antineoplastic agent:

Anticancer agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 81.39%; H 11.38%; O 7.23%	DFC
Melting Point	Mp 251-252°	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]15D +20 (Py)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Betulin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03fr-0123900000-c065f63cfc666ade1e12	Spectrum
Predicted GC-MS	Betulin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-1031190000-184b060ede0fa7d00f5f	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0000900000-22e094b6986194d96d55	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0115900000-330f02ad90f1dc19ba92	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-3498100000-08dd583786c7a035765b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0000900000-22e094b6986194d96d55	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0115900000-330f02ad90f1dc19ba92	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-3498100000-08dd583786c7a035765b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0000900000-22e094b6986194d96d55	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0115900000-330f02ad90f1dc19ba92	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-3498100000-08dd583786c7a035765b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0000900000-22e094b6986194d96d55	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0115900000-330f02ad90f1dc19ba92	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-3498100000-08dd583786c7a035765b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-05ca0bd606f47edc98c5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0001900000-f8147a299fc6f4a27886	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002e-2009800000-f3e02607e1649f1439c6	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-05ca0bd606f47edc98c5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0001900000-f8147a299fc6f4a27886	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002e-2009800000-f3e02607e1649f1439c6	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-05ca0bd606f47edc98c5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0001900000-f8147a299fc6f4a27886	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002e-2009800000-f3e02607e1649f1439c6	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000900000-05ca0bd606f47edc98c5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-0001900000-f8147a299fc6f4a27886	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002e-2009800000-f3e02607e1649f1439c6	2015-04-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36838

CRC / DFC (Dictionary of Food Compounds) ID

JVB93-S:KJC50-N

EAFUS ID

Not Available

Dr. Duke ID

BETULIN

BIGG ID

Not Available

KNApSAcK ID

C00003740

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

Betulin

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 carcinomic	35610	An agent that inhibits the growth and proliferation of cancer cells, playing a crucial role in cancer prevention and treatment. Therapeutically, it is used to manage and treat various types of cancer, reducing tumor size and slowing disease progression, with key medical uses in oncology and chemotherapy.	DUKE
Anti feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	DUKE
Anti-flu	22587	An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.	DUKE
Anti HIV	22587	An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	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
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Aphidifuge	25944	An agent that repels aphids, used in agriculture to protect plants. Biologically, it disrupts aphid feeding and reproduction. Therapeutically, it has been explored for its potential insecticidal and antiparasitic properties, with possible applications in managing insect-borne diseases and parasitic infections.	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
Hypolipemic		An agent that lowers lipid levels, treating hyperlipidemias by reducing cholesterol and triglyceride levels, with therapeutic applications in managing cardiovascular disease, atherosclerosis, and stroke prevention.	DUKE
Prostaglandin synthesis inhibitor	35222	An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs).	DUKE
Topoisomerase-II inhibitor	50750	An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.	DUKE