biotin
CHEBI:15956 EXACT SEEDED antiviralcytotoxicenzyme inhibitor
An organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thieno[3,4-d]imidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. The parent of the class of biotins.
Structure
| Standard InChIKey | YBJHBAHKTGYVGT-ZKWXMUAHSA-N |
|---|---|
| SMILES | OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12 |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA013155, pubchem:171548 |
Filing pathway
Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.
Producer organisms 2
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Aspergillus nidulans NCBITaxon:162425 |
SOURCE_ASSERTION | mibig:BGC0001238 | PMID:20713166 |
| Aspergillus nidulans NCBITaxon:162425 |
SOURCE_ASSERTION | mibig:BGC0001239 | PMID:20713166 |
Occurrences 23
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Mus musculus NCBITaxon:10090 |
CHEBI | PMID:19425150 |
| Lysinibacillus sphaericus NCBITaxon:1421 |
LOTUS | DOI:10.1271/BBB1961.49.2783 |
| Achromobacter NCBITaxon:222 |
LOTUS | DOI:10.1016/0006-291X(81)90262-X |
| Lipomyces starkeyi NCBITaxon:29829 |
LOTUS | DOI:10.2323/JGAM.20.277 |
| Glycine max NCBITaxon:3847 |
LOTUS | DOI:10.1080/09540100903203004 |
| Phaseolus vulgaris NCBITaxon:3885 |
LOTUS | DOI:10.3390/IJMS19041049 |
| Phaseolus vulgaris NCBITaxon:3885 |
LOTUS | DOI:10.3390/METABO4030599 |
| Phycomyces blakesleeanus NCBITaxon:4837 |
LOTUS | DOI:10.1016/0031-9422(96)00146-X |
| Escherichia coli NCBITaxon:562 |
LOTUS | DOI:10.1021/JA00085A061 |
| Escherichia coli NCBITaxon:562 |
LOTUS | DOI:10.1038/MSB.2011.65 |
| Escherichia coli NCBITaxon:562 |
LOTUS | DOI:10.1073/PNAS.69.8.2219 |
| Escherichia coli NCBITaxon:562 |
CHEBI | PMID:21988831 |
| Caenorhabditis elegans NCBITaxon:6239 |
LOTUS | DOI:10.3389/FMOLB.2018.00096 |
| Artemia salina NCBITaxon:85549 |
LOTUS | DOI:10.1021/JF60200A008 |
| Homo sapiens NCBITaxon:9606 |
LOTUS | DOI:10.1007/S11306-012-0464-Y |
| Homo sapiens NCBITaxon:9606 |
LOTUS | DOI:10.1007/S11306-016-1051-4 |
| Homo sapiens NCBITaxon:9606 |
LOTUS | DOI:10.1038/NBT.2488 |
| Homo sapiens NCBITaxon:9606 |
LOTUS | DOI:10.1111/J.1600-0404.1999.TB07369.X |
| Homo sapiens NCBITaxon:9606 |
CHEBI | Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992. |
| Homo sapiens NCBITaxon:9606 |
CHEBI | MTBLS87 |
| Homo sapiens NCBITaxon:9606 |
CHEBI | PMID:10577274 |
| Homo sapiens NCBITaxon:9606 |
CHEBI | Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles. |
| Aspergillus nidulans NCBITaxon:162425 |
LOTUS | DOI:10.1016/J.FGB.2010.08.004 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001238 | Aspergillus nidulans NCBITaxon:162425 |
CLUSTER_UNSTATED | genbank:FJ430072.1 |
| mibig:BGC0001239 | Aspergillus nidulans NCBITaxon:162425 |
CLUSTER_UNSTATED | genbank:FJ430073.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Causal graph — bioactivity 3 nodes, 2 edges
Biotin binds the Streptomyces avidinii streptavidin and chicken avidin subunits captured in homotetrameric biotin complexes.
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
| biotin | binds | Streptomyces avidinii streptavidin | DOI:10.1126/science.2911722 |
| biotin | binds | chicken avidin | DOI:10.1006/jmbi.1993.1321 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| Counterscreen for IDE activators: Fluorescence polarization-based biochemical high throughput dose response assay for activators of recombinant IDE | EC50 2.526 uM | pubchem.aid:588681 |
| Counterscreen for IDE activators: Fluorescence polarization-based biochemical high throughput dose response assay to identify fluorescent artifacts and/or optically active compounds | EC50 2.057 uM | pubchem.aid:588442 |
| Counterscreen for activators of insulin-degrading enzyme (IDE): fluorescence-based cell-based high throughput dose response LDH release assay to identify compounds that are cytotoxic to HEK cells or compromise cell membrane permeability | IC50 89.251 uM | pubchem.aid:588440 |
| Counterscreen for inhibitors of the interaction of the Ras and Rab interactor 1 protein (Rin1) and the c-abl oncogene 1, non-receptor tyrosine kinase (Abl): Fluorescence-based biochemical high throughput dose response assay to identify GFP inhibitors and fluorescence quenchers | IC50 67.588 uM | pubchem.aid:602182 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 0.1096 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily C Member 19 (CYP2C19) small molecule antagonists: luciferase reporter qHTS assay | 0.1096 uM | pubchem.aid:1671197 |
| Cytochrome P450 Family 2 Subfamily D Member 6 (CYP2D6) small molecule antagonists: luciferase reporter qHTS assay | 43.6486 uM | pubchem.aid:1671196 |
| Cytochrome P450 Family 2 Subfamily D Member 6 (CYP2D6) small molecule antagonists: luciferase reporter qHTS assay | 43.6486 uM | pubchem.aid:1671196 |
| Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assay | 21.8761 uM | pubchem.aid:1963596 |
| Cytochrome P450 family 3 subfamily A member 7 (CYP3A7) small molecule antagonists: luciferase cell-based qHTS assay | 21.8761 uM | pubchem.aid:1963596 |
| Discovery of Small Molecule Probes for H1N1 Influenza NS1A | IC50 0.2 uM | pubchem.aid:504329 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 1e-09 uM | PMID:8515446 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 0.0002 uM | PMID:10850797 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 0.0002 uM | PMID:10850797 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 2.8e-05 uM | PMID:12925786 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 2.8e-05 uM | PMID:12925786 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 1.1e-05 uM | PMID:12925786 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 1.1e-05 uM | PMID:12925786 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 6.9e-07 uM | PMID:12925786 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 6.9e-07 uM | PMID:12925786 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 4e-08 uM | PMID:2911722 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 0.0439 uM | PMID:9568892 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 1e-06 uM | PMID:9636711 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 1e-06 uM | PMID:9636711 |
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 1e-06 uM | PMID:9636711 |
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0001238, BGC0001239. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001238 | MIBIG | 3 |
| BGC0001239 | MIBIG | 3 |
| CHEBI:15956 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/biotin.yaml, which is generated from the committed inventories. Neither is edited by hand.