Compounds > bisnorbiotin
Page last updated: 2024-12-07

bisnorbiotin

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

Description

Bisnorbiotin is a synthetic analog of biotin, a vitamin essential for various metabolic processes. It is characterized by the absence of two methylene groups in the valeric acid side chain compared to biotin. Research on bisnorbiotin has focused on its potential applications in areas such as:

- **Inhibiting biotin-dependent enzymes:** Bisnorbiotin acts as a competitive inhibitor of biotin-dependent carboxylases, enzymes crucial for fatty acid synthesis and gluconeogenesis. This inhibition has been explored in the context of developing new drugs for metabolic diseases and cancer.

- **Studying biotin metabolism:** As a structural analog of biotin, bisnorbiotin has been used as a tool to investigate the mechanisms of biotin uptake, transport, and metabolism. It has been shown to be efficiently taken up by cells and metabolized to its corresponding tetrahydro derivative.

- **Developing novel biotin-based probes:** Bisnorbiotin's unique structural features have led to its use in the development of biotin-based probes for studying cellular processes. It can be incorporated into biomolecules or small molecules to create specific probes that can be easily detected and quantified.

- **Investigating the role of biotin in human health:** Studies have explored the potential effects of bisnorbiotin on various health outcomes, including its impact on cholesterol metabolism, immune response, and oxidative stress. However, more research is needed to fully understand the role of bisnorbiotin in human health.

The synthesis of bisnorbiotin typically involves chemical modifications of biotin, using methods such as reduction and oxidation reactions. Research on bisnorbiotin is ongoing, with ongoing investigations into its potential therapeutic applications and its role in human health.'

bisnorbiotin: bacterial catabolite of biotin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID86492
CHEBI ID89481
SCHEMBL ID10047679
MeSH IDM0042636

Synonyms (15)

Synonym
bisnorbiotin
16968-98-2
3-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]propanoic acid
1h-thieno(3,4-d)imidazole-4-propanoic acid, hexahydro-2-oxo-, (3as-(3aalpha,4beta,6aalpha))-
d-allobisnorbiotin
C20384
1h-thieno[3,4-d]imidazole-4-propanoicacid, hexahydro-2-oxo-, (3as,4s,6ar)-
hexahydro-2-oxo-1h-thieno[3,4-d]imidazole-4-propionic acid
SCHEMBL10047679
3-[(3as,4s,6ar)-2-oxo-hexahydro-1h-thieno[3,4-d]imidazolidin-4-yl]propanoic acid
CHEBI:89481
[3as-(3aa,4b,6aa)]-hexahydro-2-oxo-1h-thieno[3,4-d]imidazole-4-propanoate
Q27161674
[3as-(3aa,4b,6aa)]-hexahydro-2-oxo-1h-thieno[3,4-d]imidazole-4-propanoic acid
DTXSID301317948

Research Excerpts

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

Drug Classes (1)

ClassDescription
heterocyclic fatty acidAny fatty acid containing a ring composed of atoms including at least one heteroatom.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (8.70)18.7374
1990's13 (56.52)18.2507
2000's5 (21.74)29.6817
2010's2 (8.70)24.3611
2020's1 (4.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.53

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.

MetricThis Compound (vs All)
Research Demand Index19.53 (24.57)
Research Supply Index3.22 (2.92)
Research Growth Index5.12 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (4.35%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (95.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ammonium hydroxide
azane : Saturated acyclic nitrogen hydrides having the general formula NnHn+2.		2.0110azane;
gas molecular entity;
mononuclear parent hydride		EC 3.5.1.4 (amidase) inhibitor;
metabolite;
mouse metabolite;
neurotoxin;
NMR chemical shift reference compound;
nucleophilic reagent;
refrigerant
carbamates
[no description available]		1.9510amino-acid anion
carnitine
[no description available]		4.411amino-acid betainehuman metabolite;
mouse metabolite
choline
[no description available]		4.411cholinesallergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter;
nutrient;
plant metabolite;
Saccharomyces cerevisiae metabolite
lactic acid
Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.		2.01102-hydroxy monocarboxylic acidalgal metabolite;
Daphnia magna metabolite
phenytoin
[no description available]		2.420imidazolidine-2,4-dioneanticonvulsant;
drug allergen;
sodium channel blocker;
teratogenic agent
carbamazepine
Carbamazepine: A dibenzazepine that acts as a sodium channel blocker. It is used as an anticonvulsant for the treatment of grand mal and psychomotor or focal SEIZURES. It may also be used in the management of BIPOLAR DISORDER, and has analgesic properties.. carbamazepine : A dibenzoazepine that is 5H-dibenzo[b,f]azepine carrying a carbamoyl substituent at the azepine nitrogen, used as an anticonvulsant.		2.6930dibenzoazepine;
ureas		analgesic;
anticonvulsant;
antimanic drug;
drug allergen;
EC 3.5.1.98 (histone deacetylase) inhibitor;
environmental contaminant;
glutamate transporter activator;
mitogen;
non-narcotic analgesic;
sodium channel blocker;
xenobiotic
clofibrate
angiokapsul: contains clofibrate & insoitolnicotinate		1.9910aromatic ether;
ethyl ester;
monochlorobenzenes		anticholesteremic drug;
antilipemic drug;
geroprotector;
PPARalpha agonist
phenobarbital
Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.		2.420barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative
dehydroepiandrosterone
Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.		1.991017-oxo steroid;
3beta-hydroxy-Delta(5)-steroid;
androstanoid		androgen;
human metabolite;
mouse metabolite
lysine
Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.		2.0110aspartate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
lysine;
organic molecular entity;
proteinogenic amino acid		algal metabolite;
anticonvulsant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
leucine
Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.		4.7521amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
diethylhexyl phthalate
Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.		1.9910diester;
phthalate ester		androstane receptor agonist;
apoptosis inhibitor;
plasticiser
beta-hydroxyisovaleric acid
3-hydroxyisovaleric acid : A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency.		5.81813-hydroxy monocarboxylic acidhuman metabolite
biocytin
biocytin : A monocarboxylic acid amide that results from the formal condensation of the carboxylic acid group of biotin with the N(6)-amino group of L-lysine.		2.0110azabicycloalkane;
L-alpha-amino acid zwitterion;
L-lysine derivative;
monocarboxylic acid amide;
non-proteinogenic L-alpha-amino acid;
thiabicycloalkane;
ureas		mouse metabolite
d-biotin-d-sulfoxide
biotin sulfoxide : A sulfoxide that is the S-oxide of biotin.		3.87120biotins;
sulfoxide		metabolite
biotin sulfone
biotin sulfone: RN given for (3aS-(3aalpha,4beta,6aalpha))-isomer; structure in first source. biotin sulfone : A member of the class of biotins that is biotin sulfoxide with a sulfone group replacing the sulfoxide.		1.9910biotins;
sulfone		metabolite
valerates
Valerates: Derivatives of valeric acid, including its salts and esters.		5.8181short-chain fatty acid anion;
straight-chain saturated fatty acid anion		plant metabolite
biotin
vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.		6.78231biotins;
vitamin B7		coenzyme;
cofactor;
Escherichia coli metabolite;
fundamental metabolite;
human metabolite;
mouse metabolite;
nutraceutical;
prosthetic group;
Saccharomyces cerevisiae metabolite
3-hydroxyisovalerylcarnitine
3-hydroxyisovalerylcarnitine : An O-acylcarnitine having 3-hydroxyisovaleryl as the acyl substituent.		4.411O-acylcarnitinehuman metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		05.2441
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		01.9910
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.420
Aura
[description not available]		01.9910
Epilepsy
A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)		01.9910