BIOTIN
General Information
| Mainterm | BIOTIN |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 58-85-5 |
| Regnum |
101.9 107.100 182.8159 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 171548 |
| IUPAC Name | 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid |
| InChI | InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1 |
| InChI Key | YBJHBAHKTGYVGT-ZKWXMUAHSA-N |
| Canonical SMILES | C1C2C(C(S1)CCCCC(=O)O)NC(=O)N2 |
| Molecular Formula | C10H16N2O3S |
| Wikipedia | biotin |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 244.309 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 298.0 |
| CACTVS Substructure Key Fingerprint | A A A D c e B z M A B A A A A A A A A A A A A A A A A A A W J A A A A A A A A A A A A W A A A A A A A A H g Q Q C A A A C C j F w A S B C A L A A g g I A A C Q G A A A A A A A A B A A A I E I A A C A Q B I g g A A U Q A A M F g I g A A G Y y K C A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 104.0 |
| Monoisotopic Mass | 244.088 |
| Exact Mass | 244.088 |
| XLogP3 | None |
| XLogP3-AA | 0.3 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9383 |
| Human Intestinal Absorption | HIA+ | 0.7395 |
| Caco-2 Permeability | Caco2- | 0.7206 |
| P-glycoprotein Substrate | Substrate | 0.6413 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9561 |
| Non-inhibitor | 1.0000 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8803 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7672 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7602 |
| CYP450 2D6 Substrate | Non-substrate | 0.7872 |
| CYP450 3A4 Substrate | Non-substrate | 0.6911 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9252 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9231 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8959 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9762 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9596 |
| Non-inhibitor | 0.9145 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9598 |
| Fish Toxicity | High FHMT | 0.7316 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7604 |
| Honey Bee Toxicity | Low HBT | 0.6080 |
| Biodegradation | Not ready biodegradable | 0.8923 |
| Acute Oral Toxicity | III | 0.6733 |
| Carcinogenicity (Three-class) | Non-required | 0.6441 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5732 | LogS |
| Caco-2 Permeability | -0.0582 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0581 | LD50, mol/kg |
| Fish Toxicity | 2.3455 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.0482 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Oral. Systemic - approximately 50% |
|---|---|
| Mechanism of Toxicity | Biotin is necessary for the proper functioning of enzymes that transport carboxyl units and fix carbon dioxide, and is required for various metabolic functions, including gluconeogenesis, lipogenesis, fatty acid biosynthesis, propionate metabolism, and catabolism of branched-chain amino acids. |
| Metabolism | |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Biotin and derivatives |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Biotin and derivatives |
| Alternative Parents |
|
| Molecular Framework | Aliphatic heteropolycyclic compounds |
| Substituents | Biotin - Imidazolyl carboxylic acid derivative - Medium-chain fatty acid - Heterocyclic fatty acid - Thia fatty acid - Fatty acid - Fatty acyl - Thiolane - 2-imidazoline - Isourea - Azacycle - Dialkylthioether - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Carboxylic acid derivative - Thioether - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organonitrogen compound - Organopnictogen compound - Organooxygen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as biotin and derivatives. These are organic compounds containing a ureido (tetrahydroimidizalone) ring fused with a tetrahydrothiophene ring. |
From ClassyFire
Targets
- General Function:
- Metal ion binding
- Specific Function:
- Catalyzes the rate-limiting reaction in the biogenesis of long-chain fatty acids. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
- Gene Name:
- ACACA
- Uniprot ID:
- Q13085
- Molecular Weight:
- 265551.725 Da
References
- Leonard E, Lim KH, Saw PN, Koffas MA: Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl Environ Microbiol. 2007 Jun;73(12):3877-86. Epub 2007 Apr 27. [17468269 ]
- General Function:
- Propionyl-coa carboxylase activity
- Gene Name:
- PCCA
- Uniprot ID:
- P05165
- Molecular Weight:
- 80058.295 Da
References
- Vlasova TI, Stratton SL, Wells AM, Mock NI, Mock DM: Biotin deficiency reduces expression of SLC19A3, a potential biotin transporter, in leukocytes from human blood. J Nutr. 2005 Jan;135(1):42-7. [15623830 ]
- General Function:
- Methylcrotonoyl-coa carboxylase activity
- Specific Function:
- Carboxyltransferase subunit of the 3-methylcrotonyl-CoA carboxylase, an enzyme that catalyzes the conversion of 3-methylcrotonyl-CoA to 3-methylglutaconyl-CoA, a critical step for leucine and isovaleric acid catabolism.
- Gene Name:
- MCCC2
- Uniprot ID:
- Q9HCC0
- Molecular Weight:
- 61332.65 Da
References
- Ludke A, Kramer R, Burkovski A, Schluesener D, Poetsch A: A proteomic study of Corynebacterium glutamicum AAA+ protease FtsH. BMC Microbiol. 2007 Jan 25;7:6. [17254330 ]
- General Function:
- Sodium-dependent multivitamin transmembrane transporter activity
- Specific Function:
- Transports pantothenate, biotin and lipoate in the presence of sodium.
- Gene Name:
- SLC5A6
- Uniprot ID:
- Q9Y289
- Molecular Weight:
- 68641.27 Da
References
- Camporeale G, Zempleni J, Eissenberg JC: Susceptibility to heat stress and aberrant gene expression patterns in holocarboxylase synthetase-deficient Drosophila melanogaster are caused by decreased biotinylation of histones, not of carboxylases. J Nutr. 2007 Apr;137(4):885-9. [17374649 ]
- General Function:
- Enzyme binding
- Specific Function:
- Post-translational modification of specific protein by attachment of biotin. Acts on various carboxylases such as acetyl-CoA-carboxylase, pyruvate carboxylase, propionyl CoA carboxylase, and 3-methylcrotonyl CoA carboxylase.
- Gene Name:
- HLCS
- Uniprot ID:
- P50747
- Molecular Weight:
- 80759.345 Da
References
- Camporeale G, Giordano E, Rendina R, Zempleni J, Eissenberg JC: Drosophila melanogaster holocarboxylase synthetase is a chromosomal protein required for normal histone biotinylation, gene transcription patterns, lifespan, and heat tolerance. J Nutr. 2006 Nov;136(11):2735-42. [17056793 ]
- General Function:
- Metal ion binding
- Specific Function:
- Catalyzes the ATP-dependent carboxylation of acetyl-CoA to malonyl-CoA. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase. Involved in inhibition of fatty acid and glucose oxidation and enhancement of fat storage (By similarity). May play a role in regulation of mitochondrial fatty acid oxidation through malonyl-CoA-dependent inhibition of carnitine palmitoyltransferase 1 (By similarity).
- Gene Name:
- ACACB
- Uniprot ID:
- O00763
- Molecular Weight:
- 276538.575 Da
References
- Liu Y, Zalameda L, Kim KW, Wang M, McCarter JD: Discovery of acetyl-coenzyme A carboxylase 2 inhibitors: comparison of a fluorescence intensity-based phosphate assay and a fluorescence polarization-based ADP Assay for high-throughput screening. Assay Drug Dev Technol. 2007 Apr;5(2):225-35. [17477831 ]
- General Function:
- Methylcrotonoyl-coa carboxylase activity
- Specific Function:
- Biotin-attachment subunit of the 3-methylcrotonyl-CoA carboxylase, an enzyme that catalyzes the conversion of 3-methylcrotonyl-CoA to 3-methylglutaconyl-CoA, a critical step for leucine and isovaleric acid catabolism.
- Gene Name:
- MCCC1
- Uniprot ID:
- Q96RQ3
- Molecular Weight:
- 80472.45 Da
References
- Friebel D, von der Hagen M, Baumgartner ER, Fowler B, Hahn G, Feyh P, Heubner G, Baumgartner MR, Hoffmann GF: The first case of 3-methylcrotonyl-CoA carboxylase (MCC) deficiency responsive to biotin. Neuropediatrics. 2006 Apr;37(2):72-8. [16773504 ]
- General Function:
- Propionyl-coa carboxylase activity
- Gene Name:
- PCCB
- Uniprot ID:
- P05166
- Molecular Weight:
- 58215.13 Da
References
- Ishii M, Chuakrut S, Arai H, Igarashi Y: Occurrence, biochemistry and possible biotechnological application of the 3-hydroxypropionate cycle. Appl Microbiol Biotechnol. 2004 Jun;64(5):605-10. Epub 2004 Feb 28. [14997352 ]
- General Function:
- Pyruvate carboxylase activity
- Specific Function:
- Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
- Gene Name:
- PC
- Uniprot ID:
- P11498
- Molecular Weight:
- 129632.565 Da
References
- Ozimek PZ, Klompmaker SH, Visser N, Veenhuis M, van der Klei IJ: The transcarboxylase domain of pyruvate carboxylase is essential for assembly of the peroxisomal flavoenzyme alcohol oxidase. FEMS Yeast Res. 2007 Oct;7(7):1082-92. Epub 2007 Feb 20. [17316367 ]
- General Function:
- Syntaxin binding
- Specific Function:
- Non-receptor tyrosine-protein kinase that plays a role in many key processes linked to cell growth and survival such as cytoskeleton remodeling in response to extracellular stimuli, cell motility and adhesion, receptor endocytosis, autophagy, DNA damage response and apoptosis. Coordinates actin remodeling through tyrosine phosphorylation of proteins controlling cytoskeleton dynamics like WASF3 (involved in branch formation); ANXA1 (involved in membrane anchoring); DBN1, DBNL, CTTN, RAPH1 and ENAH (involved in signaling); or MAPT and PXN (microtubule-binding proteins). Phosphorylation of WASF3 is critical for the stimulation of lamellipodia formation and cell migration. Involved in the regulation of cell adhesion and motility through phosphorylation of key regulators of these processes such as BCAR1, CRK, CRKL, DOK1, EFS or NEDD9. Phosphorylates multiple receptor tyrosine kinases and more particularly promotes endocytosis of EGFR, facilitates the formation of neuromuscular synapses through MUSK, inhibits PDGFRB-mediated chemotaxis and modulates the endocytosis of activated B-cell receptor complexes. Other substrates which are involved in endocytosis regulation are the caveolin (CAV1) and RIN1. Moreover, ABL1 regulates the CBL family of ubiquitin ligases that drive receptor down-regulation and actin remodeling. Phosphorylation of CBL leads to increased EGFR stability. Involved in late-stage autophagy by regulating positively the trafficking and function of lysosomal components. ABL1 targets to mitochondria in response to oxidative stress and thereby mediates mitochondrial dysfunction and cell death. ABL1 is also translocated in the nucleus where it has DNA-binding activity and is involved in DNA-damage response and apoptosis. Many substrates are known mediators of DNA repair: DDB1, DDB2, ERCC3, ERCC6, RAD9A, RAD51, RAD52 or WRN. Activates the proapoptotic pathway when the DNA damage is too severe to be repaired. Phosphorylates TP73, a primary regulator for this type of damage-induced apoptosis. Phosphorylates the caspase CASP9 on 'Tyr-153' and regulates its processing in the apoptotic response to DNA damage. Phosphorylates PSMA7 that leads to an inhibition of proteasomal activity and cell cycle transition blocks. ABL1 acts also as a regulator of multiple pathological signaling cascades during infection. Several known tyrosine-phosphorylated microbial proteins have been identified as ABL1 substrates. This is the case of A36R of Vaccinia virus, Tir (translocated intimin receptor) of pathogenic E.coli and possibly Citrobacter, CagA (cytotoxin-associated gene A) of H.pylori, or AnkA (ankyrin repeat-containing protein A) of A.phagocytophilum. Pathogens can highjack ABL1 kinase signaling to reorganize the host actin cytoskeleton for multiple purposes, like facilitating intracellular movement and host cell exit. Finally, functions as its own regulator through autocatalytic activity as well as through phosphorylation of its inhibitor, ABI1.
- Gene Name:
- ABL1
- Uniprot ID:
- P00519
- Molecular Weight:
- 122871.435 Da
References
- Liu T, Lin Y, Wen X, Jorissen RN, Gilson MK: BindingDB: a web-accessible database of experimentally determined protein-ligand binding affinities. Nucleic Acids Res. 2007 Jan;35(Database issue):D198-201. Epub 2006 Dec 1. [17145705 ]
From T3DB