Record Information
Version1.0
Creation date2011-09-21 00:24:51 UTC
Update date2015-10-09 22:31:22 UTC
Primary IDFDB023111
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBiocytin
DescriptionBiocytin is a naturally occurring low molecular weight analog of biotin, and a primary source of this essential metabolite for mammals. Biotinidase acts as a hydrolase by cleaving biocytin and biotinyl-peptides, thereby liberating biotin for reutilization. Mammals cannot synthesize biotin and, therefore, derive the vitamin from dietary sources or from the endogenous turnover of the carboxylases. Free biotin can readily enter the biotin pool, whereas holocarboxylases or other biotin-containing proteins must first be degraded proteolytically to biocytin (biotinyl-e-lysine) or biotinyl-peptides. Biocytin is also an especially versatile marker for neuroanatomical investigations, shown that may have multiple applications, especially for labeling neurons. (PMID: 8930409, 1384763, 2479450) [HMDB]
CAS Number576-19-2
Structure
Thumb
Synonyms
SynonymSource
(3AS-(3aalpha,4beta,6aalpha))-N(6)-(5-(hexahydro-2-oxo-1H-thieno(3,4-D)imidazol-4-yl)-1-oxopentyl)-L-lysineChEBI
Biotinyl-L-lysineChEBI
epsilon-N-Biotinyl-L-lysineChEBI
epsilon-N-BiotinyllysineChEBI
N(epsilon)-Biotinyl-L-lysineChEBI
N-Biotinyl-L-lysineChEBI
N6-D-Biotinyl-L-lysineChEBI
N(6)-D-Biotinyl-L-lysineChEBI
(3AS-(3aalpha,4b,6aalpha))-N(6)-(5-(hexahydro-2-oxo-1H-thieno(3,4-D)imidazol-4-yl)-1-oxopentyl)-L-lysineGenerator
(3AS-(3aalpha,4β,6aalpha))-N(6)-(5-(hexahydro-2-oxo-1H-thieno(3,4-D)imidazol-4-yl)-1-oxopentyl)-L-lysineGenerator
H-Lys(biotinyl)-OHHMDB
N-epsilon-Biotin-L-lysineHMDB
N6-delta-Biotinyl-L-lysineHMDB
Ne-biotynyl-L-lysineHMDB
Ne-Biotynyl-L-lysinehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP-0.69ALOGPS
logP-2.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.24ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area133.55 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity94.66 m³·mol⁻¹ChemAxon
Polarizability40.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H28N4O4S
IUPAC name(2S)-6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamido}-2-aminohexanoic acid
InChI IdentifierInChI=1S/C16H28N4O4S/c17-10(15(22)23)5-3-4-8-18-13(21)7-2-1-6-12-14-11(9-25-12)19-16(24)20-14/h10-12,14H,1-9,17H2,(H,18,21)(H,22,23)(H2,19,20,24)/t10-,11-,12-,14-/m0/s1
InChI KeyBAQMYDQNMFBZNA-MNXVOIDGSA-N
Isomeric SMILES[H][C@]12CS[C@@H](CCCCC(=O)NCCCC[C@H](N)C(O)=O)[C@@]1([H])NC(=O)N2
Average Molecular Weight372.483
Monoisotopic Molecular Weight372.183126094
Classification
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Fatty acid
  • Fatty acyl
  • Thiolane
  • 2-imidazoline
  • Amino acid
  • Isourea
  • Azacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid
  • Thioether
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organic oxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBiocytin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0035-9633000000-af428e64c7164519343bSpectrum
Predicted GC-MSBiocytin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9745000000-c60f47e829fe15e1e793Spectrum
Predicted GC-MSBiocytin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0009000000-e021402fd0b719844eb2Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-003r-9064000000-5ce2eb2b09d3a1c52ce8Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9110000000-d9630fc3192cacdc2fdfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05di-0429000000-0bfe49385b5205b2e046Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fc1-3922000000-9e29cfc78fb1faa6e51bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9500000000-e9574b5d68137a62b679Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-105dd5c3f301cc7dc40eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9437000000-8ea9d972c1d5eeb423e9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-6a46fba2d13aba09d4f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-29850915bb5c6d661d6dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-1129000000-d0a10775c2694ba6ee3eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7910000000-0d78214d8d0838c98e75Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-fc712e350aa1f6640bd7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9133000000-748bb305ae1784021d66Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9100000000-e607ed2f383027caf589Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID75634
ChEMBL IDNot Available
KEGG Compound IDC05552
Pubchem Compound ID83814
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03134
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID46012
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
BiotinidaseBTDP43251
Signal peptidase complex subunit 1SPCS1Q9Y6A9
Pathways
NameSMPDB LinkKEGG Link
Biotin MetabolismSMP00066 map00780
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference