Cannabis Compound Database: Showing Compound Card for Biotin (CDB004786)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (9)transporters (1) Show 16 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:36:37 UTC

Updated at

2020-12-07 19:10:55 UTC

CannabisDB ID

CDB004786

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Biotin

Description

Biotin, also known as D-biotin or coenzyme R, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). An organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thienoimidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. Biotin exists in all living species, ranging from bacteria to humans. In humans, biotin is involved in the metabolic disorder called the multiple carboxylase deficiency, neonatal or early onset form pathway. Biotin is a potentially toxic compound. Biotin is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

244.31

Monoisotopic Molecular Weight

244.0882

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

All tissues

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Role

Industrial application:

Personal care products

Food and nutrition:

Nutritional supplement

Pharmaceutical industry:

Pharmaceutical

Biological role:

Essential vitamin

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-01pt-9500000000-a1e1ec56cf32236ac6b1	Spectrum
GC-MS	Biotin, non-derivatized, GC-MS Spectrum	splash10-0f76-1960000000-b21ddd69490cac3254f8	Spectrum
GC-MS	Biotin, 3 TMS, GC-MS Spectrum	splash10-0f76-3960000000-a8a94e2de123f66979d8	Spectrum
GC-MS	Biotin, non-derivatized, GC-MS Spectrum	splash10-0f76-1960000000-b21ddd69490cac3254f8	Spectrum
GC-MS	Biotin, non-derivatized, GC-MS Spectrum	splash10-0f76-3960000000-a8a94e2de123f66979d8	Spectrum
Predicted GC-MS	Biotin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-6910000000-11bfe0a5a77f7dfaa8c5	Spectrum
Predicted GC-MS	Biotin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9680000000-eb01d8147a82f7982b54	Spectrum
Predicted GC-MS	Biotin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Biotin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Biotin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Biotin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Biotin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Biotin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Biotin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0090000000-6d956bb533d353d449c9	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-0190000000-01f67d1bdf8c742e48c8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0fxx-3920000000-f0b9613cbd9371e4be92	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9400000000-107f2a44f521c2513578	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0006-9000000000-1a3f65d909dc40055e87	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-004i-0090000000-c928e8d0a18f3f848262	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-066s-1920000000-5f795e0b7f1d7cf986e5	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0ar1-1920000000-c298be862857cb3bbc7f	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000t-0900000000-cdc4a4c359ff765fd32d	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-05xs-1920000000-3be430b63e9c748c681a	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0090000000-bcffb0dcf77e8fd727a4	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f6x-0390000000-c209523d36e9a7681f44	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0090000000-c0f81ee86772310db415	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0190000000-016eb89528e564c74720	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0fxx-3920000000-f0b9613cbd9371e4be92	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9400000000-107f2a44f521c2513578	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-d08e1b3709844e1e91b0	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0190000000-21d0f2512788276bbb89	Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udj-0690000000-dc372934024e58bdcc60	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0290000000-43932f104dea28cbdfb8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1960000000-d3673c6bc624b97f35be	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9600000000-00a4e152d89024a9b423	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1390000000-3f4b512cfa57b894ff94	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6y-7890000000-ea1e647fc5b31e42af0b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e139c928dcc46b225bdb	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Biotin Metabolism
Alanine Metabolism
Primary Hyperoxaluria Type I		Not Available
Pyruvate Carboxylase Deficiency		Not Available
Lactic Acidemia		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acetyl-CoA carboxylase 2	ACACB	12q24.11	O00763	details
Pyruvate carboxylase, mitochondrial	PC	11q13.4-q13.5	P11498	details
Acetyl-CoA carboxylase 1	ACACA	17q21	Q13085	details
Propionyl-CoA carboxylase beta chain, mitochondrial	PCCB	3q21-q22	P05166	details
Propionyl-CoA carboxylase alpha chain, mitochondrial	PCCA	13q32	P05165	details
Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial	MCCC2	5q12-q13	Q9HCC0	details
Biotin--protein ligase	HLCS	21q22.13	P50747	details
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial	MCCC1	3q27	Q96RQ3	details
Biotinidase	BTD	3p25	P43251	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sodium-dependent multivitamin transporter	SLC5A6	2p23	Q9Y289	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acetyl-CoA carboxylase 2	ACACB	12q24.11	O00763	details
Pyruvate carboxylase, mitochondrial	PC	11q13.4-q13.5	P11498	details
Acetyl-CoA carboxylase 1	ACACA	17q21	Q13085	details
Propionyl-CoA carboxylase alpha chain, mitochondrial	PCCA	13q32	P05165	details
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial	MCCC1	3q27	Q96RQ3	details
Cytochrome P450 1B1	CYP1B1	2p22.2	Q16678	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

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

General References

Not Available

Only showing the first 10 proteins. There are 16 proteins in total.

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Enzymes

Enzyme Details

1. Acetyl-CoA carboxylase 2

General function:: Involved in acetyl-CoA carboxylase activity
Specific function:: ACC-beta may be involved in the provision of malonyl-CoA or in the regulation of fatty acid oxidation, rather than fatty acid biosynthesis. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
Gene Name:: ACACB
Uniprot ID:: O00763
Molecular weight:: 276538.575

Enzyme Details

2. Pyruvate carboxylase, mitochondrial

General function:: Involved in catalytic 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

Enzyme Details

3. Acetyl-CoA carboxylase 1

General function:: Involved in acetyl-CoA carboxylase activity
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:: 269997.01

Enzyme Details

4. Propionyl-CoA carboxylase beta chain, mitochondrial

General function:: Involved in ligase activity
Specific function:: Not Available
Gene Name:: PCCB
Uniprot ID:: P05166
Molecular weight:: 58215.13

Enzyme Details

5. Propionyl-CoA carboxylase alpha chain, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: PCCA
Uniprot ID:: P05165
Molecular weight:: 80058.295

Enzyme Details

6. Methylcrotonoyl-CoA carboxylase beta chain, mitochondrial

General function:: Involved in ligase activity
Specific function:: Not Available
Gene Name:: MCCC2
Uniprot ID:: Q9HCC0
Molecular weight:: 61332.65

Enzyme Details

7. Biotin--protein ligase

General function:: Involved in biotin-[acetyl-CoA-carboxylase] ligase activity
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

Enzyme Details

8. Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: MCCC1
Uniprot ID:: Q96RQ3
Molecular weight:: 80472.45

Enzyme Details

9. Biotinidase

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:: Catalytic release of biotin from biocytin, the product of biotin-dependent carboxylases degradation.
Gene Name:: BTD
Uniprot ID:: P43251
Molecular weight:: 61132.43

Transporters

Enzyme Details

1. Sodium-dependent multivitamin transporter

General function:: Involved in transporter activity
Specific function:: Transports pantothenate, biotin and lipoate in the presence of sodium.
Gene Name:: SLC5A6
Uniprot ID:: Q9Y289
Molecular weight:: 68641.27

Only showing the first 10 proteins. There are 16 proteins in total.

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Showing Compound Card for Biotin (CDB004786)

Structure for CDB004786 (Biotin)

Enzymes

Transporters