Record Information
Version2.0
Creation Date2012-05-31 10:23:03 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00177
Identification
Name:L-Histidine
Description:Histidine is an amino acid. It is a precursor for histamine and carnosine biosynthesis. The enzyme histidine ammonia-lyase converts histidine into ammonia and urocanic acid. (Wikipedia)
Structure
Thumb
Synonyms:
  • α-amino-4-imidazoleproprionate
  • α-amino-4-imidazoleproprionic acid
  • (S)-α-amino-1H-imidazole-4-propanoate
  • (S)-α-amino-1H-imidazole-4-propanoic acid
  • (S)-1H-Imidazole-4-alanine
  • (S)-2-Amino-3-(4-imidazolyl)propionsaeure
  • (S)-4-(2-Amino-2-carboxyethyl)imidazole
  • (S)-a-Amino-1H-imidazole-4-propanoate
  • (S)-a-Amino-1H-imidazole-4-propanoic acid
  • (S)-a-amino-1H-Imidazole-4-propionate
  • (S)-a-amino-1H-Imidazole-4-propionic acid
  • (S)-alpha-Amino-1H-imidazole-4-propanoate
  • (S)-alpha-Amino-1H-imidazole-4-propanoic acid
  • (S)-alpha-Amino-1H-imidazole-4-propionate
  • (S)-alpha-Amino-1H-imidazole-4-propionic acid
  • (S)-Histidine
  • (S)-α-amino-1H-Imidazole-4-propanoate
  • (S)-α-amino-1H-Imidazole-4-propanoic acid
  • (S)-α-amino-1H-Imidazole-4-propionate
  • (S)-α-amino-1H-Imidazole-4-propionic acid
  • (S)1H-Imidazole-4-alanine
  • 3-(1H-Imidazol-4-yl)-L-Alanine
  • a-amino-4-Imidazoleproprionate
  • a-amino-4-Imidazoleproprionic acid
  • Alpha-Amino-4-imidazoleproprionate
  • Alpha-Amino-4-imidazoleproprionic acid
  • Amino-1H-imidazole-4-propanoate
  • Amino-1H-imidazole-4-propanoic acid
  • Amino-4-imidazoleproprionate
  • Amino-4-imidazoleproprionic acid
  • Glyoxaline-5-alanine
  • H
  • His
  • Histidine
  • L-(-)-Histidine
  • α-amino-4-Imidazoleproprionate
  • α-amino-4-Imidazoleproprionic acid
Chemical Formula:C6H9N3O2
Weight:Average: 155.1546
Monoisotopic: 155.069476547
InChI Key:HNDVDQJCIGZPNO-YFKPBYRVSA-N
InChI:InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1
CAS number:71-00-1
IUPAC Name:(2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
Traditional IUPAC Name:L-histidine
SMILES:N[C@@H](CC1=CN=CN1)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as histidine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • Aralkylamine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:287 °C
Experimental Properties:
PropertyValueSource
Water Solubility:45.6 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-3.32 [CHMELIK,J ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility62.0 mg/mLALOGPS
logP-3.1ALOGPS
logP-3.6ChemAxon
logS-0.4ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.06 m3·mol-1ChemAxon
Polarizability14.67 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Secondary Metabolites: Histidine biosynthesisPW000984 Pw000984Pw000984 greyscalePw000984 simple
beta-Alanine metabolismPW000896 Pw000896Pw000896 greyscalePw000896 simple
histidine biosynthesisPW000810 Pw000810Pw000810 greyscalePw000810 simple
tRNA Charging 2PW000803 Pw000803Pw000803 greyscalePw000803 simple
tRNA chargingPW000799 Pw000799Pw000799 greyscalePw000799 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
68± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
175± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
98± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
52± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
235± 26 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
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0.22± 0.01 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
Download Details
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0940000000-43b9b035189af65e19cbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-0910000000-fc3ecec9d4ff3aa8cb09View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-0910000000-8284a673a35f7ac2241fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fk9-8910000000-a3231b1a418b5798ecacView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0udi-1920000000-227e8116769731104e82View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0ufu-2942100000-31605fd50ecc1f5be0edView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-001i-9500000000-1d29684ccb6383687865View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0940000000-43b9b035189af65e19cbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0910000000-fc3ecec9d4ff3aa8cb09View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0910000000-8284a673a35f7ac2241fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQsplash10-0002-2901100000-ae0f3865934743de764cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fk9-8910000000-a3231b1a418b5798ecacView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0udi-1920000000-227e8116769731104e82View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0ufu-2942100000-31605fd50ecc1f5be0edView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0ue9-0900000000-75e38a3f347210c301b0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0910000000-c54bd92cc112eec7e509View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-03di-6900000000-1dd400a16b8067f4daeaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-21530fac9975dc1edc7cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-9300000000-a946c375931adb366aaeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053r-9000000000-61a3602d80bc0d54c579View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-7d63b501889c2628f4f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d4ccd4e44ca818b4cb17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-811aee5724fe0999c134View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-2900000000-052753eb699ae7cb4cb9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-3e145a05e6a71a0a2f56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-143a4b9d88183bc5abe7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-a8c213472da676a241f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-dfdf9562f155abb5fdebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0uk9-0879331100-8434b5b9e7e5700c2353View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-aaaaadcecd4cd7c94e1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-90c4cbd09d7abc003013View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-1381708d18c24486773dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0w29-0696321100-eb62fc608270d1151707View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-3450566ff38e6506a70fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01q9-7900000000-124509a66476629ce10aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-efa6a21b1be16fda0802View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-137840e69da48c6114e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udu-3900000000-06d50e90c797793a72d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9100000000-de7c9eb8068ef4f39f85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00l6-9000000000-ebf778679d4c6d6a6057View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-9000000000-08d0188684283d1b2372View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0900000000-46c2f608d27f0381a039View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
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  • Janknecht R, Hipskind RA, Houthaeve T, Nordheim A, Stunnenberg HG: Identification of multiple SRF N-terminal phosphorylation sites affecting DNA binding properties. EMBO J. 1992 Mar;11(3):1045-54. Pubmed: 1547771
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  • Masini E, Fabbroni V, Giannini L, Vannacci A, Messerini L, Perna F, Cortesini C, Cianchi F: Histamine and histidine decarboxylase up-regulation in colorectal cancer: correlation with tumor stage. Inflamm Res. 2005 Apr;54 Suppl 1:S80-1. Pubmed: 15928846
  • Mason AB, Halbrooks PJ, James NG, Connolly SA, Larouche JR, Smith VC, MacGillivray RT, Chasteen ND: Mutational analysis of C-lobe ligands of human serum transferrin: insights into the mechanism of iron release. Biochemistry. 2005 Jun 7;44(22):8013-21. Pubmed: 15924420
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  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  • Sieja K, Stanosz S, von Mach-Szczypinski J, Olewniczak S, Stanosz M: Concentration of histamine in serum and tissues of the primary ductal breast cancers in women. Breast. 2005 Jun;14(3):236-41. Epub 2005 Jan 21. Pubmed: 15927833
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Watanabe M, Suliman ME, Qureshi AR, Garcia-Lopez E, Barany P, Heimburger O, Stenvinkel P, Lindholm B: Consequences of low plasma histidine in chronic kidney disease patients: associations with inflammation, oxidative stress, and mortality. Am J Clin Nutr. 2008 Jun;87(6):1860-6. Pubmed: 18541578
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Synthesis Reference:Aurelio Luigi; Brownlee Robert T C; Hughes Andrew B A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan. Organic letters (2002), 4(21), 3767-9.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15971
HMDB IDHMDB00177
Pubchem Compound ID6274
Kegg IDC00135
ChemSpider ID6038
WikipediaL-Histidine
BioCyc IDHIS
EcoCyc IDHIS
Ligand ExpoHIS_LFZW_DHE2

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the sequential NAD-dependent oxidations of L- histidinol to L-histidinaldehyde and then to L-histidine
Gene Name:
hisD
Uniprot ID:
P06988
Molecular weight:
46110
Reactions
L-histidinol + H(2)O + 2 NAD(+) = L-histidine + 2 NADH.
General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for histidine. Probably responsible for energy coupling to the transport system
Gene Name:
hisP
Uniprot ID:
P07109
Molecular weight:
28653
General function:
Involved in nucleotide binding
Specific function:
ATP + L-histidine + tRNA(His) = AMP + diphosphate + L-histidyl-tRNA(His)
Gene Name:
hisS
Uniprot ID:
P60906
Molecular weight:
47029
Reactions
ATP + L-histidine + tRNA(His) = AMP + diphosphate + L-histidyl-tRNA(His).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
Gene Name:
hisM
Uniprot ID:
P0AEU3
Molecular weight:
26870
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
Gene Name:
hisQ
Uniprot ID:
P52094
Molecular weight:
24649
General function:
Involved in transporter activity
Specific function:
Component of the high-affinity histidine permease, a binding-protein-dependent transport system. The other components are proteins hisQ, hisM, and hisP
Gene Name:
hisJ
Uniprot ID:
P0AEU0
Molecular weight:
28483

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the binding-protein-dependent transport system for histidine. Probably responsible for energy coupling to the transport system
Gene Name:
hisP
Uniprot ID:
P07109
Molecular weight:
28653
General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Uniprot ID:
P37774
Molecular weight:
27677
General function:
Involved in transporter activity
Specific function:
Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
Gene Name:
yecS
Uniprot ID:
P0AFT2
Molecular weight:
24801
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
Gene Name:
hisM
Uniprot ID:
P0AEU3
Molecular weight:
26870
General function:
Involved in transport
Specific function:
Permease that is involved in the transport across the cytoplasmic membrane of the aromatic amino acids (phenylalanine, tyrosine, and tryptophan)
Gene Name:
aroP
Uniprot ID:
P15993
Molecular weight:
49690
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for histidine; probably responsible for the translocation of the substrate across the membrane
Gene Name:
hisQ
Uniprot ID:
P52094
Molecular weight:
24649
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
Component of the high-affinity histidine permease, a binding-protein-dependent transport system. The other components are proteins hisQ, hisM, and hisP
Gene Name:
hisJ
Uniprot ID:
P0AEU0
Molecular weight:
28483
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368