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Identification
YMDB IDYMDB00702
NameL-histidinol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTopiramate, also known as topamax or MCN-4853, belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring. Topiramate is an extremely weak basic (essentially neutral) compound (based on its pKa). Topiramate is a bitter tasting compound. Outside of the human body,. Topiramate is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (S)-beta-Amino-1H-imidazole-4-propanol
  • HSO
  • 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate
  • 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate
  • MCN-4853
  • RWJ-17021
  • Tipiramate
  • Tipiramato
  • Topamax
  • Topiramato
  • Topiramatum
  • TPM
  • Trokendi XR
  • 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamate
  • 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamic acid
  • 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamate
  • 2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamic acid
  • 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamic acid
  • 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamate
  • 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamic acid
  • 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
  • 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamic acid
  • 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamate
  • 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamic acid
  • 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamate
  • 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamic acid
  • 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamate
  • 2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamic acid
  • 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamic acid
  • 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamate
  • 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamic acid
  • 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamate
  • 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamic acid
  • 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamate
  • 2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamic acid
  • Tipiramic acid
  • Topiramic acid
  • Epitomax
  • Topamax sprinkle
  • Topomax
  • 2,3-4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate
  • 4-[(S)-2-amino-3-Hydroxypropyl]imidazole
  • Histidinol
  • Imidazole C-4(5) deriv. 4
  • Histidol
  • Lacto-N-fuco-pentaose I
  • LNF 1
  • LNF I
  • LNFP I
CAS number4836-52-6
WeightAverage: 141.171
Monoisotopic: 141.090211989
InChI KeyZQISRDCJNBUVMM-YFKPBYRVSA-N
InChIInChI=1S/C6H11N3O/c7-5(3-10)1-6-2-8-4-9-6/h2,4-5,10H,1,3,7H2,(H,8,9)/t5-/m0/s1
IUPAC Name(2S)-2-amino-3-(1H-imidazol-5-yl)propan-1-ol
Traditional IUPAC NameHSO
Chemical FormulaC6H11N3O
SMILESN[C@H](CO)CC1=CNC=N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDioxolopyrans
Sub ClassNot Available
Direct ParentDioxolopyrans
Alternative Parents
Substituents
  • Dioxolopyran
  • Ketal
  • Oxane
  • Monosaccharide
  • Organic sulfuric acid or derivatives
  • Meta-dioxolane
  • Oxacycle
  • Acetal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility129 g/LALOGPS
logP-1.3ALOGPS
logP-1.7ChemAxon
logS-0.04ALOGPS
pKa (Strongest Acidic)13.45ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area74.93 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.19 m³·mol⁻¹ChemAxon
Polarizability14.74 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Histidine BiosynthesisPW002418 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Histidine metabolismec00340 Map00340
SMPDB Reactions
L-histidinol + NADhydron + NADH + Histidinal
L-histidinol phosphate + waterL-histidinol + phosphate
KEGG Reactions
water + NAD + L-histidinolNADH + L-Histidine + hydron
L-histidinol phosphate + waterphosphate + L-histidinol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-1970000000-5f8fce52ae008e9577d3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-1960000000-2bd5915e1e2204265b30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0udi-0960000000-04ea4478dfe81318bf5cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fk9-9540000000-9d5008be3cb2086af6f4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1970000000-5f8fce52ae008e9577d3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1960000000-2bd5915e1e2204265b30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0960000000-04ea4478dfe81318bf5cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-9540000000-9d5008be3cb2086af6f4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-5900000000-b7271e5101b1cf971b24JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03e9-9800000000-eb7ec98ac413a4a5067dJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006x-1900000000-c360dc1772243d0c7ccaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-eba5a77ea4a62d8375f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-009922321d7904037f80JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0900000000-3a563827d1023d4dadd7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00e9-7900000000-4baa9781af4596ef1a49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-98f4a65357b52f544e0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-5921f5ed9c6159fbe48eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9000000000-a7a82388a3feef766362JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0089-8900000000-b7fa72e4e20dbc5d79d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-3a563827d1023d4dadd7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00e9-7900000000-4baa9781af4596ef1a49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-98f4a65357b52f544e0cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-5921f5ed9c6159fbe48eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-128590ab44ecade57be8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0089-8900000000-b7fa72e4e20dbc5d79d2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-e19200b81166dd2ceb6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-3900000000-8073bbe0237addc54c81JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5a-9300000000-a833e6da71592c915e87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-f2eb428fd58c551e9f84JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0596-9800000000-7dcca6b55761d69a3dc2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9100000000-4649be9a2b45a85f4de1JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Raju, R. V., Datla, R. S., Warrington, R. C., Sharma, R. K. (1998). "Effects of L-histidine and its structural analogues on human N-myristoyltransferase activity and importance of EEVEH amino acid sequence for enzyme activity." Biochemistry 37:14928-14936.9778369
  • Vallen, E. (2002). "Analysis of protein localization and secretory pathway function using the yeast Saccharomyces cerevisiae." Cell Biol Educ 1:173-192.12669100
Synthesis Reference:Beltra, A. P.; Bonete, P.; Gonzalez-Garcia, J.; Garcia-Garcia, V.; Montiel, V. Electrochemical synthesis of L-histidinol using solvated electrons. Journal of the Electrochemical Society (2005), 152(4), D65-D68.
External Links:
ResourceLink
CHEBI ID16255
HMDB IDHMDB03431
Pubchem Compound ID165271
Kegg IDC00860
ChemSpider ID144886
FOODB IDFDB023601
Wikipedia IDTopiramate
BioCyc IDL-HISTIDINOL-P

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
1-(5-phosphoribosyl)-AMP + H(2)O = 1-(5- phosphoribosyl)-5-((5- phosphoribosylamino)methylideneamino)imidazole-4-carboxamide
Gene Name:
HIS4
Uniprot ID:
P00815
Molecular weight:
87720.5
Reactions
1-(5-phosphoribosyl)-AMP + H(2)O → 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide.
1-(5-phosphoribosyl)-ATP + H(2)O → 1-(5-phosphoribosyl)-AMP + diphosphate.
L-histidinol + H(2)O + 2 NAD(+) → L-histidine + 2 NADH.
General function:
Involved in histidinol-phosphatase activity
Specific function:
L-histidinol phosphate + H(2)O = L-histidinol + phosphate
Gene Name:
HIS2
Uniprot ID:
P38635
Molecular weight:
38581.5
Reactions
L-histidinol phosphate + H(2)O → L-histidinol + phosphate.