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58-85-5 molecular structure
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5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid

ChemBase ID: 8
Molecular Formular: C10H16N2O3S
Molecular Mass: 244.31064
Monoisotopic Mass: 244.08816338
SMILES and InChIs

SMILES:
S1[C@H]([C@H]2NC(=O)N[C@H]2C1)CCCCC(=O)O
Canonical SMILES:
OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
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
InChIKey:
YBJHBAHKTGYVGT-ZKWXMUAHSA-N

Cite this record

CBID:8 http://www.chembase.cn/molecule-8.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
IUPAC Traditional name
biotin
5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
Brand Name
Biodermatin
Bioepiderm
Bios II
Factor S
Lutavit H2
Meribin
Rovimix H2
Biotin Forte
Synonyms
(+)-Biotin
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid
Vitamin H
Vitamin B7
D(+)-Biotin
D-Biotin
Coenzyme R
Biotin
Bioepiderm
Factor S
D(+)-Biotin
5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid
D-BIOTIN, USP GRADE
Biotin
Vitamin B7
Biopeiderm
Biotinum
Bios II
D-BIOTIN
Biotin
(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic Acid
Lutavit H2
Meribin
NSC 63865
Rovimix H2
Vitamin B 7
D-Biotin
Biotin 生物素
维生素 B7
维生素 H
辅酶 R
生物素
生物素
吡哆素
D-生物素
CAS Number
58-85-5
EC Number
200-399-3
MDL Number
MFCD00005541
Beilstein Number
86838
PubChem SID
160963471
24891512
24851733
24891716
46508694
24891795
24871542
24891778
PubChem CID
171548
CHEBI ID
15956
ATC CODE
A11HA05
CHEMBL
857
Chemspider ID
149962
DrugBank ID
DB00121
KEGG ID
D00029
Unique Ingredient Identifier
6SO6U10H04
Wikipedia Title
Biotin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.4043164  H Acceptors
H Donor LogD (pH = 5.5) -0.8081781 
LogD (pH = 7.4) -2.5652478  Log P 0.31942365 
Molar Refractivity 60.0509 cm3 Polarizability 23.706692 Å3
Polar Surface Area 78.43 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.17  LOG S -2.3 
Solubility (Water) 1.22e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 M NaOH: soluble10 mg/mL at 25 °C, clear, colorless expand Show data source
0.22 mg/mL at 25 oC [MERCK INDEX (1996)] expand Show data source
22 mg/100 mL in water expand Show data source
H2O: soluble0.2 mg/mL (Solubility increases with addition of 1 N NaOH.) expand Show data source
Water expand Show data source
Apperance
lyophilized powder expand Show data source
powder expand Show data source
White crystalline needles expand Show data source
White Solid expand Show data source
Melting Point
229-234 °C expand Show data source
231-233 °C(lit.) expand Show data source
232-233 expand Show data source
232-233 °C expand Show data source
232-233°C expand Show data source
Optical Rotation
[α]20/D +91±2°, c = 1% in 0.1 M NaOH expand Show data source
Hydrophobicity(logP)
0.5 expand Show data source
Storage Condition
2-8°C expand Show data source
Refrigerator expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
XJ9088200 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
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German water hazard class
1 expand Show data source
TSCA Listed
false expand Show data source
NFPA704
NFPA 704 diagram
1
1
0
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Mechanism of Action
Cofactor responsible for carbon dioxide transfer expand Show data source
Purity
≥98.0% expand Show data source
≥99% expand Show data source
≥99% (TLC) expand Show data source
≥99.0% (T) expand Show data source
95+% expand Show data source
Grade
analytical standard expand Show data source
certified reference material expand Show data source
Ph Eur expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Packaging
ampule of 100 mg expand Show data source
Suitability
meets USP testing specifications expand Show data source
plant cell culture tested expand Show data source
suitable for cell culture expand Show data source
suitable for insect cell culture expand Show data source
suitable for plant cell culture expand Show data source
Ignition Residue
≤0.1% (as SO4) expand Show data source
Cation Traces
Ca: ≤50 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤10 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Na: ≤500 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Biological Source
Occurs in yeast, eggs and liver. Also prod. by various other microorganisms and isol. from various higher plant sources, e.g. maize seedlings, leaves of Raphanus sativus expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Loss on Drying
≤0.5% loss on drying expand Show data source
Application(s)
Additive for cosmetic and feedstuffs expand Show data source
Bacterial growth factor for ""egg white injury"" expand Show data source
Quality Level
PREMIUM expand Show data source
Feature
standard type water soluble vitamin expand Show data source
Pharmacopeia
testing & handling conforms to Pharmacopeia expand Show data source
Empirical Formula (Hill Notation)
C10H16N2O3S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals TRC TRC Wikipedia Wikipedia
DrugBank - DB00121 external link
Item Information
Drug Groups approved; nutraceutical
Description A water-soluble, enzyme co-factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. [PubChem]
Indication For nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology Biotin is a water-soluble B-complex vitamin which is composed of an ureido ring fused with a tetrahydrothiophene ring. A valeric acid substituent is attached to one of the carbon atoms of the tetrahydrothiophene ring. Biotin is used in cell growth, the production of fatty acids, metabolism of fats, and amino acids. It plays a role in the Kreb cycle, which is the process in which energy is released from food. Biotin not only assists in various metabolic chemical conversions, but also helps with the transfer of carbon dioxide. Biotin is also helpful in maintaining a steady blood sugar level. Biotin is often recommended for strengthening hair and nails. Consequenty, it is found in many cosmetic and health products for the hair and skin. Biotin deficiency is a rare nutritional disorder caused by a deficiency of biotin. Initial symptoms of biotin deficiency include: Dry skin, Seborrheic dermatitis, Fungal infections, rashes including erythematous periorofacial macular rash, fine and brittle hair, and hair loss or total alopecia. If left untreated, neurological symptoms can develop, including mild depression, which may progress to profound lassitude and, eventually, to somnolence; changes in mental status, generalized muscular pains (myalgias), hyperesthesias and paresthesias. The treatment for biotin deficiency is to simply start taking some biotin supplements. A lack of biotin in infants will lead to a condition called seborrheic dermatitis or "cradle cap". Biotin deficiencies are extremely rare in adults but if it does occur, it will lead to anemia, depression, hair loss, high blood sugar levels, muscle pain, nausea, loss of appetite and inflamed mucous membranes.
Toxicity Prolonged skin contact may cause irritation.
Affected Organisms
Humans and other mammals
Absorption Systemic - approximately 50%
References
Holmberg A, Blomstergren A, Nord O, Lukacs M, Lundeberg J, Uhlen M: The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis. 2005 Feb;26(3):501-10. [Pubmed]
External Links
Wikipedia
PDRhealth
Drugs.com
Sigma Aldrich - B4639 external link
Biochem/physiol Actions
对于氨基酸、能量代谢和脂肪酸合成有重要作用的必要维生素。它是四种哺乳类动物羧化酶中的辅基,促进二氧化碳的结合与输送。
Sigma Aldrich - 91827 external link
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - 14400 external link
Other Notes
Reviews1,2; Avidin-Biotin technology;
Sigma Aldrich - 47868 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Sigma Aldrich - B4501 external link
Application
可用于从抗生物素蛋白/链霉抗生物素蛋白树脂上洗脱蛋白质。
包装
1, 5, 10, 25 g in poly bottle
100, 500 mg in poly bottle
Sigma Aldrich - B0301 external link
Biochem/physiol Actions
对于氨基酸、能量代谢和脂肪酸合成有重要作用的必要维生素。它是四种哺乳类动物羧化酶中的辅基,促进二氧化碳的结合与输送。
MP Biomedicals - 02194634 external link
Cell Culture Reagent
Crystalline
MP Biomedicals - 02199537 external link
Solid
MP Biomedicals - 02101023 external link
Crystalline
Toronto Research Chemicals - B389040 external link
Growth factor present in minute amounts in every living cell. Plays an indispensable role in numerous naturally occurring carboxylation reactions. Occurs mainly bound to proteins or polypeptides. The richest sources are liver, kidney, pancreas, yeast, and

REFERENCES

REFERENCES

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