rhododendrol

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

Description

rhododendrol: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	919205
CHEMBL ID	1086681
SCHEMBL ID	13698052
MeSH ID	M0298328

Synonyms (32)

Synonym
rhododendrol
4-[(3r)-3-hydroxybutyl]phenol
CHEMBL1086681
(-)-rhododendrol
unii-97ptr2f3z8
rhododendrol, (-)-
betuligenol, (-)-
2-butanol, 4-(p-hydroxyphenyl)-
501-96-2
97ptr2f3z8 ,
(-)-betuligenol
(r)-frambinol
benzenepropanol, 4-hydroxy-alpha-methyl-, (alphar)-
(r)-(-)-rhododendrol
benzenepropanol, 4-hydroxy-alpha-methyl-, (r)-
benzenepropanol, 4-hydroxy-.alpha.-methyl-, (r)-
benzenepropanol, 4-hydroxy-.alpha.-methyl-, (.alpha.r)-
4r-(4-hydroxyphenyl)-2-butanol
SCHEMBL13698052
SFUCGABQOMYVJW-MRVPVSSYSA-N
benzenepropanol, 4-hydroxy-.alpha.-methyl-, (-)-
p-(3-hydroxybutyl)phenol, (r)-
DTXSID20198211
AKOS032948275
mfcd20274761
(r)-4-(3-hydroxybutyl)phenol
AS-18098
(r)-(-)-rhododendrol; (r)-frambinol; betuligenol; betuligenol, (-)-; rhododendrol; rhododendrol, (-)-
Q27272029
EN300-1870666
HY-N0948
CS-0016082

Research Excerpts

Overview

Rhododendrol (RD) is a potent tyrosinase inhibitor that is metabolized to RD-quinone. It may underlie the cytotoxicity of RD and leukoderma of the skin that may result.

Excerpt	Reference	Relevance
"Rhododendrol (RD) is a potent tyrosinase inhibitor that is metabolized to RD-quinone by tyrosinase, which may underlie the cytotoxicity of RD and leukoderma of the skin that may result. "	( NAD(P)H dehydrogenase, quinone 1 (NQO1), protects melanin-producing cells from cytotoxicity of rhododendrol. Akasaka, T; Maesawa, C; Masuda, T; Okubo, A; Shibazaki, M; Takahashi, K; Yasuhira, S, 2016)	2.1
"Rhododendrol is a phenolic compound that shows a tyrosinase-dependent toxicity for melanocytes and occasionally induces a vitiligo-like skin depigmentation. "	( Glutathione maintenance is crucial for survival of melanocytes after exposure to rhododendrol. Hachiya, A; Inoue, S; Kawabata, K; Kondo, M; Sato, K; Takahashi, Y; Yamaguchi, S, 2016)	2.1

Toxicity

Excerpt	Reference	Relevance
" Our results help to elucidate the development mechanisms of RD-induced leukoderma and provide information for innovation of safe skin-whitening compounds."	( 4-(4-Hydroxyphenyl)-2-butanol (rhododendrol)-induced melanocyte cytotoxicity is enhanced by UVB exposure through generation of oxidative stress. Goto, N; Ito, S; Masaki, T; Nagai, H; Nishigori, C; Tsujimoto, M; Wakamatsu, K, 2018)	0.77

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

Bioassays (2)

Assay ID	Title	Year	Journal	Article
AID480668	Inhibition of anti-DNP-IgE-induced degranulation in rat RBL2H3 cells assessed as betahexosaminidase released at 100 uM after 20 mins by microplate reader assay	2010	Bioorganic & medicinal chemistry letters, May-01, Volume: 20, Issue:9	Inhibition of antigen-induced degranulation by aryl compounds isolated from the bark of Betula platyphylla in RBL-2H3 cells.
AID480667	Inhibition of anti-DNP-IgE-induced degranulation in rat RBL2H3 cells assessed as betahexosaminidase released at 10 uM after 20 mins by microplate reader assay	2010	Bioorganic & medicinal chemistry letters, May-01, Volume: 20, Issue:9	Inhibition of antigen-induced degranulation by aryl compounds isolated from the bark of Betula platyphylla in RBL-2H3 cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (57)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (1.75)	18.2507
2000's	0 (0.00)	29.6817
2010's	42 (73.68)	24.3611
2020's	14 (24.56)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.15

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	31.15 (24.57)
Research Supply Index	4.11 (2.92)
Research Growth Index	6.91 (4.65)
Search Engine Demand Index	36.71 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (31.15)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	3 (5.26%)	5.53%
Reviews	5 (8.77%)	6.00%
Case Studies	2 (3.51%)	4.05%
Observational	0 (0.00%)	0.25%
Other	47 (82.46%)	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
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	10.18	55	3	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
catechol [no description available]	2.11	1	0	catechols	allelochemical; genotoxin; plant metabolite
dihydroxyacetone [no description available]	7.25	1	0	ketotriose; primary alpha-hydroxy ketone	antifungal agent; Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dihydroxyphenylalanine Dihydroxyphenylalanine: A beta-hydroxylated derivative of phenylalanine. The D-form of dihydroxyphenylalanine has less physiologic activity than the L-form and is commonly used experimentally to determine whether the pharmacological effects of LEVODOPA are stereospecific.. dopa : A hydroxyphenylalanine carrying hydroxy substituents at positions 3 and 4 of the benzene ring.	2.11	1	0	hydroxyphenylalanine; non-proteinogenic alpha-amino acid; tyrosine derivative	human metabolite
caffeine [no description available]	2.31	1	0	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
penicillamine Penicillamine: 3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.. penicillamine : An alpha-amino acid having the structure of valine substituted at the beta position with a sulfanyl group.	7.6	1	0	non-proteinogenic alpha-amino acid; penicillamine	antirheumatic drug; chelator; copper chelator; drug allergen
butylphen butylphen: irritant; structure. 4-tert-butylphenol : A member of the class of phenols that is phenol substituted with a tert-butyl group at position 4.	3.21	1	0	phenols	allergen
monobenzone monobenzone: structure. monobenzone : The monobenzyl ether of hydroquinone. It is used as a topical drug for medical depigmentation.	8.62	2	0	benzyl ether	allergen; dermatologic drug; melanin synthesis inhibitor
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.21	1	0	pyrrole; secondary amine
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.13	1	0	adamantanes; polycyclic alkane
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.17	1	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
raspberry ketone rheosmin: an NSAID that blocks NF-kappaB activation; isolated from Pinus densiflora; structure in first source. raspberry ketone : A ketone that is 4-phenylbutan-2-one in which the phenyl ring is substituted at position 4 by a hydroxy group. It is found in a variety of fruits including raspberries, blackberries and cranberries, and is used in perfumery and cosmetics.	3.11	4	0	methyl ketone; phenols	androgen antagonist; cosmetic; flavouring agent; fragrance; hepatoprotective agent; metabolite
hydroiodic acid hydrogen iodide : A diatomic molecule containing covalently bonded hydrogen and iodine atoms.	2.11	1	0	gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
salvin salvin: a biocyclic diterpenoid; from sage and rosemary (Lamiaceae)	2.13	1	0	abietane diterpenoid; carbotricyclic compound; catechols; monocarboxylic acid	angiogenesis modulating agent; anti-inflammatory agent; antineoplastic agent; antioxidant; apoptosis inducer; food preservative; HIV protease inhibitor; plant metabolite
4-(4-hydroxyphenyl)-2-butanol 4-(4-hydroxyphenyl)-2-butanol: Depigmenting Agent	2.13	1	0	phenols
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	7.17	1	0	oxygen hydride; oxygen radical; reactive oxygen species
4-n-butylresorcinol 4-n-butylresorcinol: structure in first source	2.13	1	0	resorcinols
dopaquinone [no description available]	2.11	1	0	1,2-benzoquinones; amino acid zwitterion; L-phenylalanine derivative	human metabolite; mouse metabolite
Rhododendrin rhododendrin: isolated from leaves of Rhododendron plants; has anti-inflammatory properties	2.05	1	0	glycoside
glycosides [no description available]	2.51	2	0
phenylthiourea Phenylthiourea: Phenylthiourea is a THIOUREA derivative containing a phenyl ring. Depending on their genetic makeup, humans can find it either bitter-tasting or tasteless.. N-phenylthiourea : A member of the class of thioureas that is thiourea in which one of the hydrogens is replaced by a phenyl group. Depending on their genetic makeup, humans find it either very bitter-tasting or tasteless. This unusual property resulted in N-phenylthiourea being used in paternity testing prior to the advent of DNA testing.	2.1	1	0	thioureas	EC 1.14.18.1 (tyrosinase) inhibitor
quercetin [no description available]	2.05	1	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
cholecalciferol Cholecalciferol: Derivative of 7-dehydroxycholesterol formed by ULTRAVIOLET RAYS breaking of the C9-C10 bond. It differs from ERGOCALCIFEROL in having a single bond between C22 and C23 and lacking a methyl group at C24.. calciol : A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.	9.04	2	1	D3 vitamins; hydroxy seco-steroid; seco-cholestane; secondary alcohol; steroid hormone	geroprotector; human metabolite
shogaol shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source	2.25	1	0	enone; monomethoxybenzene; phenols
bimatoprost Bimatoprost: A cloprostenol-derived amide that is used as an ANTIHYPERTENSIVE AGENT in the treatment of OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.	3.98	2	1	monocarboxylic acid amide	antiglaucoma drug; antihypertensive agent
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	7.15	1	0	cysteinium	fundamental metabolite
platyphylloside platyphylloside: from the bark of black alder, inhibits the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells; structure in first source	2.05	1	0
mart-1 antigen MART-1 Antigen: A melanosome-specific protein that plays a role in the expression, stability, trafficking, and processing of GP100 MELANOMA ANTIGEN, which is critical to the formation of Stage II MELANOSOMES. The protein is used as an antigen marker for MELANOMA cells.	2.81	3	0
tofacitinib tofacitinib : A pyrrolopyrimidine that is pyrrolo[2,3-d]pyrimidine substituted at position 4 by an N-methyl,N-(1-cyanoacetyl-4-methylpiperidin-3-yl)amino moiety. Used as its citrate salt to treat moderately to severely active rheumatoid arthritis.	7.21	1	0	N-acylpiperidine; nitrile; pyrrolopyrimidine; tertiary amino compound	antirheumatic drug; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
(E)-1,7-Bis(4-hydroxyphenyl)hept-4-en-3-one [no description available]	2.05	1	0	diarylheptanoid
piperidines Piperidines: A family of hexahydropyridines.	2.21	1	0
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.1	1	0
5-adamantan-1-yl-n-(2,4-dihydroxybenzyl)-2,4-dimethoxybenzamide 5-adamantan-1-yl-N-(2,4-dihydroxybenzyl)-2,4-dimethoxybenzamide: a tyrosinase inhibitor; structure in first source	2.13	1	0

Condition	Relationship Strength	Studies	Trials
Hypomelanosis [description not available]	8.17	28	1
Hypopigmentation A condition caused by a deficiency or a loss of melanin pigmentation in the epidermis, also known as hypomelanosis. Hypopigmentation can be localized or generalized, and may result from genetic defects, trauma, inflammation, or infections.	8.17	28	1
Malignant Melanoma [description not available]	2.61	2	0
Melanoma A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)	7.61	2	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.6	1	0
Vitiligo A disorder consisting of areas of macular depigmentation, commonly on extensor aspects of extremities, on the face or neck, and in skin folds. Age of onset is often in young adulthood and the condition tends to progress gradually with lesions enlarging and extending until a quiescent state is reached.	7.17	16	2
Genetic Predisposition [description not available]	2.25	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.26	5	0
Dermatitis Medicamentosa [description not available]	2.53	2	0
Experimental Neoplasms [description not available]	3.59	1	1
Mole, Skin [description not available]	3.95	2	1
Cancer of Skin [description not available]	3.94	2	1
Skin Neoplasms Tumors or cancer of the SKIN.	3.94	2	1
Allergic Reaction [description not available]	2.21	1	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	2.21	1	0
B16 Melanoma [description not available]	2.81	3	0
Allergic Contact Dermatitis [description not available]	7.11	1	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.11	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.13	1	0
Dermatoses [description not available]	3.45	2	0
Incontinentia Pigmenti Achromians [description not available]	3.03	1	0
Skin Diseases Diseases involving the DERMIS or EPIDERMIS.	3.45	2	0
Contact Dermatitis [description not available]	2.13	1	0
Dermatitis, Contact A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.	2.13	1	0

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