Record Information
Version1.0
Created at2020-04-17 18:36:37 UTC
Updated at2020-12-07 19:10:55 UTC
CannabisDB IDCDB004786
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameBiotin
DescriptionBiotin, 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
Thumb
Synonyms
ValueSource
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acidChEBI
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valeric acidChEBI
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoic acidChEBI
BiotinaChEBI
BiotineChEBI
BiotinumChEBI
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acidChEBI
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acidChEBI
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valeric acidChEBI
Coenzyme RChEBI
D-(+)-BiotinChEBI
D-BiotinChEBI
Vitamin b7ChEBI
Vitamin HChEBI
BioepidermKegg
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valerateGenerator
(3AS,4S,6ar)-hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-valerateGenerator
5-(2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-yl)pentanoateGenerator
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valerateGenerator
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valerateGenerator
cis-Tetrahydro-2-oxothieno(3,4-D)imidazoline-4-valerateGenerator
(+)-BiotinHMDB
-(+)-BiotinHMDB
1SWKHMDB
1SWNHMDB
1SWRHMDB
BiodermatinHMDB
Bios HHMDB
Bios IIHMDB
D(+)-BiotinHMDB
D-Biotin factor SHMDB
delta-(+)-BiotinHMDB
delta-BiotinHMDB
delta-Biotin factor SHMDB
Factor SHMDB
Factor S (vitamin)HMDB
Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoateHMDB
Hexahydro-2-oxo-1H-thieno(3,4-D)imidazole-4-pentanoic acidHMDB
Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoateHMDB
Hexahydro-2-oxo-[3as-(3aa,4b,6aa)]-1H-thieno[3,4-D]imidazole-4-pentanoic acidHMDB
Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoateHMDB
Hexahydro-2-oxo-[3as-(3alpha,4beta,6alpha)]-1H-thieno[3,4-D]imidazole-4-pentanoic acidHMDB
Lutavit H2HMDB
MeribinHMDB
Rovimix H 2HMDB
Vitamin-HHMDB
Biotin hermes brandHMDB
Biotin roche brandHMDB
Biotin simons brandHMDB
Biotin strathmann brandHMDB
Biotin ziethen brandHMDB
Biotin ratiopharmHMDB
Roche brand OF biotinHMDB
Roche, biotineHMDB
E+b pharma brand OF biotinHMDB
MedobiotinHMDB
BiokurHMDB
BiotinratiopharmHMDB
Gelfert, biotinHMDB
Hermes brand OF biotinHMDB
Hermes, biotinHMDB
Medopharm brand OF biotinHMDB
Ratiopharm brand OF biotinHMDB
Biocur brand OF biotinHMDB
Biotin dermapharm brandHMDB
Biotine rocheHMDB
DeacuraHMDB
Dermapharm brand OF biotinHMDB
GabunatHMDB
MedebiotinHMDB
RombellinHMDB
Ziethen brand OF biotinHMDB
Biotin biocur brandHMDB
Biotin gelfertHMDB
Biotin hermesHMDB
Biotin medopharm brandHMDB
Biotin ratiopharm brandHMDB
Biotin-ratiopharmHMDB
H, VitaminHMDB
Medea brand OF biotin sodium saltHMDB
Simons brand OF biotinHMDB
Strathmann brand OF biotinHMDB
Chemical FormulaC10H16N2O3S
Average Molecular Weight244.31
Monoisotopic Molecular Weight244.0882
IUPAC Name5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
Traditional Name5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
CAS Registry Number58-85-5
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 KeyYBJHBAHKTGYVGT-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBiotin and derivatives
Sub ClassNot Available
Direct ParentBiotin 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 FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point232 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.22 mg/mL at 25 °CNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.17ALOGPS
logP0.32ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity60.05 m³·mol⁻¹ChemAxon
Polarizability24.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01pt-9500000000-a1e1ec56cf32236ac6b1Spectrum
GC-MSBiotin, non-derivatized, GC-MS Spectrumsplash10-0f76-1960000000-b21ddd69490cac3254f8Spectrum
GC-MSBiotin, 3 TMS, GC-MS Spectrumsplash10-0f76-3960000000-a8a94e2de123f66979d8Spectrum
GC-MSBiotin, non-derivatized, GC-MS Spectrumsplash10-0f76-1960000000-b21ddd69490cac3254f8Spectrum
GC-MSBiotin, non-derivatized, GC-MS Spectrumsplash10-0f76-3960000000-a8a94e2de123f66979d8Spectrum
Predicted GC-MSBiotin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-6910000000-11bfe0a5a77f7dfaa8c5Spectrum
Predicted GC-MSBiotin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9680000000-eb01d8147a82f7982b54Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0090000000-6d956bb533d353d449c9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-0190000000-01f67d1bdf8c742e48c8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fxx-3920000000-f0b9613cbd9371e4be92Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9400000000-107f2a44f521c2513578Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-1a3f65d909dc40055e87Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-0090000000-c928e8d0a18f3f848262Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-066s-1920000000-5f795e0b7f1d7cf986e5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0ar1-1920000000-c298be862857cb3bbc7fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000t-0900000000-cdc4a4c359ff765fd32dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05xs-1920000000-3be430b63e9c748c681aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0006-0090000000-bcffb0dcf77e8fd727a4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f6x-0390000000-c209523d36e9a7681f44Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0090000000-c0f81ee86772310db415Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0190000000-016eb89528e564c74720Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fxx-3920000000-f0b9613cbd9371e4be92Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9400000000-107f2a44f521c2513578Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d08e1b3709844e1e91b0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0190000000-21d0f2512788276bbb89Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0690000000-dc372934024e58bdcc60Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0290000000-43932f104dea28cbdfb8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1960000000-d3673c6bc624b97f35beSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-00a4e152d89024a9b423Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1390000000-3f4b512cfa57b894ff94Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6y-7890000000-ea1e647fc5b31e42af0bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e139c928dcc46b225bdbSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Acetyl-CoA carboxylase 2ACACB12q24.11O00763 details
Pyruvate carboxylase, mitochondrialPC11q13.4-q13.5P11498 details
Acetyl-CoA carboxylase 1ACACA17q21Q13085 details
Propionyl-CoA carboxylase beta chain, mitochondrialPCCB3q21-q22P05166 details
Propionyl-CoA carboxylase alpha chain, mitochondrialPCCA13q32P05165 details
Methylcrotonoyl-CoA carboxylase beta chain, mitochondrialMCCC25q12-q13Q9HCC0 details
Biotin--protein ligaseHLCS21q22.13P50747 details
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrialMCCC13q27Q96RQ3 details
BiotinidaseBTD3p25P43251 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Sodium-dependent multivitamin transporterSLC5A62p23Q9Y289 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Acetyl-CoA carboxylase 2ACACB12q24.11O00763 details
Pyruvate carboxylase, mitochondrialPC11q13.4-q13.5P11498 details
Acetyl-CoA carboxylase 1ACACA17q21Q13085 details
Propionyl-CoA carboxylase alpha chain, mitochondrialPCCA13q32P05165 details
Methylcrotonoyl-CoA carboxylase subunit alpha, mitochondrialMCCC13q27Q96RQ3 details
Cytochrome P450 1B1CYP1B12p22.2Q16678 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000030
DrugBank IDDB00121
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014510
KNApSAcK IDC00000756
Chemspider ID149962
KEGG Compound IDC00120
BioCyc IDBIOTIN
BiGG ID33931
Wikipedia LinkBiotin
METLIN ID243
PubChem Compound171548
PDB IDNot Available
ChEBI ID15956
References
General ReferencesNot Available

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

Enzymes

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
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
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
General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
PCCB
Uniprot ID:
P05166
Molecular weight:
58215.13
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PCCA
Uniprot ID:
P05165
Molecular weight:
80058.295
General function:
Involved in ligase activity
Specific function:
Not Available
Gene Name:
MCCC2
Uniprot ID:
Q9HCC0
Molecular weight:
61332.65
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
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
MCCC1
Uniprot ID:
Q96RQ3
Molecular weight:
80472.45
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

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.