Milk Composition Database: Showing metabocard for Biotin (BMDB0000030)

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Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:18:40 UTC

Update Date

2020-06-04 20:42:57 UTC

MCDB ID

BMDB0000030

Secondary Accession Numbers

BMDB00030

Metabolite Identification

Common Name

Biotin

Description

Biotin, also known as D-biotin or biotin ratiopharm, 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. Biotin is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Biotin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Biotin exists in all living species, ranging from bacteria to humans. In cattle, biotin is involved in the metabolic pathway called the biotin metabolism pathway. Biotin is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid	ChEBI
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acid	ChEBI
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acid	ChEBI
Biotina	ChEBI
Biotine	ChEBI
Biotinum	ChEBI
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid	ChEBI
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid	ChEBI
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valeric acid	ChEBI
Coenzyme R	ChEBI
D-(+)-Biotin	ChEBI
D-Biotin	ChEBI
Vitamin b7	ChEBI
Vitamin H	ChEBI
Bioepiderm	Kegg
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valerate	Generator
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerate	Generator
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoate	Generator
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valerate	Generator
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valerate	Generator
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valerate	Generator
(+)-Biotin	HMDB
-(+)-Biotin	HMDB
1SWK	HMDB
1SWN	HMDB
1SWR	HMDB
Biodermatin	HMDB
Bios H	HMDB
Bios II	HMDB
D(+)-Biotin	HMDB
D-Biotin factor S	HMDB
delta-(+)-Biotin	HMDB
delta-Biotin	HMDB
delta-Biotin factor S	HMDB
Factor S	HMDB
Factor S (vitamin)	HMDB
Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoate	HMDB
Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoic acid	HMDB
Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoate	HMDB
Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoic acid	HMDB
Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoate	HMDB
Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoic acid	HMDB
Lutavit H2	HMDB
Meribin	HMDB
Rovimix H 2	HMDB
Vitamin-H	HMDB
Biotin hermes brand	HMDB
Biotin roche brand	HMDB
Biotin simons brand	HMDB
Biotin strathmann brand	HMDB
Biotin ziethen brand	HMDB
Biotin ratiopharm	HMDB
Roche brand OF biotin	HMDB
Roche, biotine	HMDB
E+b pharma brand OF biotin	HMDB
Medobiotin	HMDB
Biokur	HMDB
Biotinratiopharm	HMDB
Gelfert, biotin	HMDB
Hermes brand OF biotin	HMDB
Hermes, biotin	HMDB
Medopharm brand OF biotin	HMDB
Ratiopharm brand OF biotin	HMDB
Biocur brand OF biotin	HMDB
Biotin dermapharm brand	HMDB
Biotine roche	HMDB
Deacura	HMDB
Dermapharm brand OF biotin	HMDB
Gabunat	HMDB
Medebiotin	HMDB
Rombellin	HMDB
Ziethen brand OF biotin	HMDB
Biotin biocur brand	HMDB
Biotin gelfert	HMDB
Biotin hermes	HMDB
Biotin medopharm brand	HMDB
Biotin ratiopharm brand	HMDB
Biotin-ratiopharm	HMDB
H, Vitamin	HMDB
Medea brand OF biotin sodium salt	HMDB
Simons brand OF biotin	HMDB
Strathmann brand OF biotin	HMDB

Chemical Formula

C₁₀H₁₆N₂O₃S

Average Molecular Weight

244.311

Monoisotopic Molecular Weight

244.088163078

IUPAC Name

5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid

Traditional Name

5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid

CAS Registry Number

58-85-5

SMILES

[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2

InChI Identifier

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

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Biotin and derivatives

Sub Class

Not Available

Direct Parent

Biotin and derivatives

Alternative Parents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

biotins (CHEBI:15956 )
Water-soluble vitamins (C00120 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	232 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.22 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.17	ALOGPS
logP	0.32	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	60.05 m³·mol⁻¹	ChemAxon
Polarizability	24.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0f76-1960000000-b21ddd69490cac3254f8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0f76-3960000000-a8a94e2de123f66979d8	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f76-1960000000-b21ddd69490cac3254f8	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f76-3960000000-a8a94e2de123f66979d8	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6910000000-11bfe0a5a77f7dfaa8c5	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9680000000-eb01d8147a82f7982b54	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0090000000-6d956bb533d353d449c9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-0190000000-01f67d1bdf8c742e48c8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0fxx-3920000000-f0b9613cbd9371e4be92	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9400000000-107f2a44f521c2513578	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-1a3f65d909dc40055e87	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-004i-0090000000-c928e8d0a18f3f848262	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-066s-1920000000-5f795e0b7f1d7cf986e5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0ar1-1920000000-c298be862857cb3bbc7f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000t-0900000000-cdc4a4c359ff765fd32d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-05xs-1920000000-3be430b63e9c748c681a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0090000000-bcffb0dcf77e8fd727a4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f6x-0390000000-c209523d36e9a7681f44	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0090000000-c0f81ee86772310db415	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0190000000-016eb89528e564c74720	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fxx-3920000000-f0b9613cbd9371e4be92	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9400000000-107f2a44f521c2513578	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d08e1b3709844e1e91b0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0190000000-21d0f2512788276bbb89	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udj-0690000000-dc372934024e58bdcc60	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0290000000-43932f104dea28cbdfb8	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1960000000-d3673c6bc624b97f35be	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-00a4e152d89024a9b423	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1390000000-3f4b512cfa57b894ff94	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6y-7890000000-ea1e647fc5b31e42af0b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e139c928dcc46b225bdb	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01pt-9500000000-a1e1ec56cf32236ac6b1	2018-05-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.1 uM	Fooddata+, T...	details
Detected and Quantified	0.041 uM	Fooddata+, T...	details
Detected and Quantified	0.082 uM	Fooddata+, T...	details
Detected and Quantified	0.078 uM	Fooddata+, T...	details
Detected and Quantified	0.082 uM	Fooddata+, T...	details
Detected and Quantified	0.082 uM	Fooddata+, T...	details
Detected and Quantified	0.064 uM	Fooddata+, T...	details
Detected and Quantified	0.041 uM	Fooddata+, T...	details
Detected and Quantified	0.041 uM	Park, Y. W; Juáre...	details
Detected and Quantified	0.080 +/- 0.003 uM	PMID: 30994344	details
Detected and Quantified	0.097 +/- 0.004 uM	PMID: 30994344	details
Detected and Quantified	0.090 +/- 0.003 uM	PMID: 30994344	details
Detected and Quantified	0.090 +/- 0.002 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000030

DrugBank ID

DB00121

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15956

References

Synthesis Reference

Corey, E. J.; Mehrotra, Mukund M. A simple and enantioselective synthesis of (+)-biotin. Tetrahedron Letters (1988), 29(1), 57-60.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Biotin (BMDB0000030)

Structure for BMDB0000030 (Biotin)