Page last updated: 2024-12-11

bo 653

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2,3-dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran: an antiatherogenic antioxidant; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	9800472
CHEMBL ID	104186
SCHEMBL ID	5055886
MeSH ID	M0277494

Synonyms (17)

Synonym
CHEMBL104186
bo-653
157360-23-1
2,3-dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran
2vsp9t5lrx ,
unii-2vsp9t5lrx
bo 653
2,3-dihydro-5-hydroxy-4,6-di-tert-butyl-2,2-dipentylbenzofuran
4,6-ditert-butyl-2,2-dipentyl-3h-benzofuran-5-ol
4,6-di-t-butyl-5-hydroxy-2,2-di-n-pentyl-2,3-dihydrobenzofuran
AGURKSYKTJQPNA-UHFFFAOYSA-N
4,6-di-tert-butyl-5-hydroxy-2,2-dipentyl-2,3-dihydrobenzofuran
SCHEMBL5055886
DTXSID20166253
4,6-bis(1,1-dimethylethyl)-2,3-dihydro-2,2-dipentyl-5-benzofuranol
5-benzofuranol, 4,6-bis(1,1-dimethylethyl)-2,3-dihydro-2,2-dipentyl-
4,6-ditert-butyl-2,2-dipentyl-3h-1-benzofuran-5-ol

Research Excerpts

Bioavailability

Excerpt	Reference	Relevance
"We examined the design of the versatile novel self-emulsifying drug delivery systems (SEDDS) type O/W microemulsion formulation which enhances the oral bioavailability by raising the solubility of poorly water soluble compounds."	( The novel formulation design of self-emulsifying drug delivery systems (SEDDS) type O/W microemulsion I: enhancing effects on oral bioavailability of poorly water soluble compounds in rats and beagle dogs. Araya, H; Hayashi, M; Nagao, S; Tomita, M, 2005)	0.33

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (12)

Assay ID	Title	Year	Journal	Article
AID29847	Distribution of compound into HDL lipoprotein fraction of WHHL Rabbit's plasma after oral administration	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID29926	Distribution of compound into VLDL lipoprotein fraction of WHHL Rabbit's plasma after oral administration	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID26958	cLogP was determined	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID28408	Distribution of compound into WHHL Rabbit's plasma after oral administration	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID100078	Inhibition of LDL oxidation induced by cupric ions (CuSO4) at 1 uM expressed as % control.	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID100079	Inhibition of LDL oxidation induced by cupric ions (CuSO4) at 10 uM expressed as % control.	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID100080	Inhibition of LDL oxidation induced by soybean lipoxygenase (SLO) at 0.5 uM expressed as % control.	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID27547	Distribution of compound into LDL lipoprotein fraction of WHHL Rabbit's plasma after oral administration	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID100081	Inhibition of LDL oxidation induced by soybean lipoxygenase (SLO) at 5 uM expressed as % control.	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID326215	Antioxidant activity assessed as oxygen radical scavenging activity in presence of human plasma by ORAC method relative to control	2008	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 18, Issue:7	Antioxidant capacity of BO-653, 2,3-dihydro-5-hydroxy-4,6-di-tert-butyl-2,2-dipentylbenzofuran, and uric acid as evaluated by ORAC method and inhibition of lipid peroxidation.
AID226841	Inhibition of MCLA chemiluminescence generated by autoxidation of linoleic acid	2003	Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14	Design and synthesis of 4,6-di-tert-butyl-2,3-dihydro-5-benzofuranols as a novel series of antiatherogenic antioxidants.
AID326216	Antioxidant activity in human plasma assessed as inhibition of cholesteryl ester hydroperoxide formation after 60 mins relative to control	2008	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 18, Issue:7	Antioxidant capacity of BO-653, 2,3-dihydro-5-hydroxy-4,6-di-tert-butyl-2,2-dipentylbenzofuran, and uric acid as evaluated by ORAC method and inhibition of lipid peroxidation.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	5 (21.74)	18.2507
2000's	16 (69.57)	29.6817
2010's	2 (8.70)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.39

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	16.39 (24.57)
Research Supply Index	3.26 (2.92)
Research Growth Index	4.46 (4.65)
Search Engine Demand Index	10.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (16.39)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (4.17%)	5.53%
Reviews	4 (16.67%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	19 (79.17%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
choline [no description available]	2.03	1	0	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	3.82	2	1	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
2,2'-azobis(2-amidinopropane) 2,2'-azobis(2-amidinopropane): water-soluble free-radical initiator	1.99	1	0	monoazo compound
ibuprofen Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine	2.02	1	0	monocarboxylic acid	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic
ketoprofen Ketoprofen: An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It is used in the treatment of rheumatoid arthritis and osteoarthritis.. ketoprofen : An oxo monocarboxylic acid that consists of propionic acid substituted by a 3-benzoylphenyl group at position 2.	2.02	1	0	benzophenones; oxo monocarboxylic acid	antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic
probucol Probucol: A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).. probucol : A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood.	4.2	5	0	dithioketal; polyphenol	anti-inflammatory drug; anticholesteremic drug; antilipemic drug; antioxidant; cardiovascular drug
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	2.02	1	0	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
aniline [no description available]	2.05	1	0	anilines; primary arylamine
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	3.12	1	0	dialdehyde	biomarker
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	6.29	11	1	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
2-tert-butylhydroquinone 2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.	2	1	0	hydroquinones	food antioxidant
pyranine pyranine: structure	2.04	1	0	organic sodium salt	fluorochrome
2,2'-azobis(2,4-dimethylvaleronitrile) 2,2'-azobis(2,4-dimethylvaleronitrile): free radical initiator in liposome systems	2.4	2	0
succinobucol succinobucol: monosuccinic acid ester of probucol; a metabolically stable modification of probucol, an equipotent antioxidant to probucol but is pharmacologically distinct	3.12	1	0	benzoate ester; phenols
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	7.83	23	1
bilirubin [no description available]	3.41	1	1	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.43	2	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.01	1	0	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
8-epi-prostaglandin f2alpha 8-epi-prostaglandin F2alpha: a potent preglomerular vasoconstrictor acting principally through thromboxane A2 receptor activation. 8-epi-prostaglandin F2alpha : An isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.	2.43	2	0	F2-isoprostane	biomarker; bronchoconstrictor agent; vasoconstrictor agent
methyl linoleate [no description available]	2.4	2	0	fatty acid methyl ester	plant metabolite
1-palmitoyl-2-linoleoylphosphatidylcholine [no description available]	2.01	1	0
ag-041r AG-041R: structure in first source	2.02	1	0
tocotrienols tocotrienol : A tocol in which the hydrocarbon chain at position 2 contains three double bonds.	2.02	1	0	diterpenoid
ubiquinol ubiquinol: reduced forms of ubiquinone; see also record for ubiquinol 10. ubiquinol-10 : A ubiquinol in which the polyprenyl substituent is decaprenyl.	2.02	1	0	polyprenylhydroquinone; ubiquinol	biomarker; metabolite
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.4	2	0	1,2-diacyl-sn-glycero-3-phosphocholine
ubiquinone Ubiquinone: A lipid-soluble benzoquinone which is involved in ELECTRON TRANSPORT in mitochondrial preparations. The compound occurs in the majority of aerobic organisms, from bacteria to higher plants and animals.	2.43	2	0
cholesteryl ester hydroperoxide cholesteryl ester hydroperoxide: RN given refers to the (3-beta)-isomer; do not confuse with cholesterol hydroperoxide (5-hydroperoxycholesterol)	3.41	1	1
hydroxyoctadecadienoic acid hydroxyoctadecadienoic acid: structure in first source	2.72	3	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	4.65	6	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent

Condition	Relationship Strength	Studies
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	5	9
Atherogenesis [description not available]	3.64	3
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.94	4
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	3.64	3
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	2.08	1
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	2.08	1
Coronary Restenosis Recurrent narrowing or constriction of a coronary artery following surgical procedures performed to alleviate a prior obstruction.	2.93	1
Choline Deficiency A condition produced by a deficiency of CHOLINE in animals. Choline is known as a lipotropic agent because it has been shown to promote the transport of excess fat from the liver under certain conditions in laboratory animals. Combined deficiency of choline (included in the B vitamin complex) and all other methyl group donors causes liver cirrhosis in some animals. Unlike compounds normally considered as vitamins, choline does not serve as a cofactor in enzymatic reactions. (From Saunders Dictionary & Encyclopedia of Laboratory Medicine and Technology, 1984)	2.03	1
Liver Steatosis [description not available]	2.03	1
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	2.03	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.94	1
Deficiency, Vitamin E [description not available]	2.03	1
Hyperlipemia [description not available]	2.03	1
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.03	1
Injury, Ischemia-Reperfusion [description not available]	1.99	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	1.99	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	1.99	1

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