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Showing NP-Card for N-Acetylhistidine (NP0333865)

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Record Information
Version2.0
Created at2024-09-09 21:01:01 UTC
Updated at2024-09-09 21:01:01 UTC
NP-MRD IDNP0333865
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Acetylhistidine
DescriptionConstituent of the tissues of various fish and amphibian subspecies N-Acetylhistidine is found in fishes.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333865 (N-Acetylhistidine)


  Mrv2104 05242323332D          

 14 14  0  0  0  0            999 V2000
    0.5678    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  6  2  0  0  0  0
  3  9  1  0  0  0  0
  4  9  2  0  0  0  0
  4 10  1  0  0  0  0
  5 11  2  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8 13  2  0  0  0  0
  8 14  1  0  0  0  0
M  END
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3D MOL for NP0333865 (N-Acetylhistidine)

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3D SDF for NP0333865 (N-Acetylhistidine)

  Mrv2104 05242323332D          

 14 14  0  0  0  0            999 V2000
    0.5678    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  6  2  0  0  0  0
  3  9  1  0  0  0  0
  4  9  2  0  0  0  0
  4 10  1  0  0  0  0
  5 11  2  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8 13  2  0  0  0  0
  8 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(O)=N\C(CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C8H11N3O3/c1-5(12)11-7(8(13)14)2-6-3-9-4-10-6/h3-4,7H,2H2,1H3,(H,9,10)(H,11,12)(H,13,14)

> <INCHI_KEY>
KBOJOGQFRVVWBH-UHFFFAOYNA-N

> <FORMULA>
C8H11N3O3

> <MOLECULAR_WEIGHT>
197.194

> <EXACT_MASS>
197.080041226

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.815651647786034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(Z)-(1-hydroxyethylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid

> <JCHEM_LOGP>
-1.5900007385531811

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.739111128770752

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5811329524155284

> <JCHEM_PKA_STRONGEST_BASIC>
6.80243067765145

> <JCHEM_POLAR_SURFACE_AREA>
98.57000000000001

> <JCHEM_REFRACTIVITY>
48.0245

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(Z)-(1-hydroxyethylidene)amino]-3-(3H-imidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333865 (N-Acetylhistidine)
Download
PDB for NP0333865 (N-Acetylhistidine)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         0                                  
HETATM    1  C   UNK     0       1.060   8.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   6.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.608   3.620   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       2.306   1.175   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      -0.274   5.930   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.941   4.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.608   2.080   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6    7                                                       
CONECT    3    6    9                                                       
CONECT    4    9   10                                                       
CONECT    5    1   11   12                                                  
CONECT    6    2    3   10                                                  
CONECT    7    2    8   11                                                  
CONECT    8    7   13   14                                                  
CONECT    9    3    4                                                       
CONECT   10    4    6                                                       
CONECT   11    5    7                                                       
CONECT   12    5                                                            
CONECT   13    8                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0333865 (N-Acetylhistidine)
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SMILES for NP0333865 (N-Acetylhistidine)
C\C(O)=N\C(CC1=CN=CN1)C(O)=O
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INCHI for NP0333865 (N-Acetylhistidine)
InChI=1/C8H11N3O3/c1-5(12)11-7(8(13)14)2-6-3-9-4-10-6/h3-4,7H,2H2,1H3,(H,9,10)(H,11,12)(H,13,14)
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H11N3O3
Average Mass197.1940 Da
Monoisotopic Mass197.08004 Da
IUPAC Name2-[(Z)-(1-hydroxyethylidene)amino]-3-(1H-imidazol-5-yl)propanoic acid
Traditional Name2-[(Z)-(1-hydroxyethylidene)amino]-3-(3H-imidazol-4-yl)propanoic acid
CAS Registry NumberNot Available
SMILES
C\C(O)=N\C(CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1/C8H11N3O3/c1-5(12)11-7(8(13)14)2-6-3-9-4-10-6/h3-4,7H,2H2,1H3,(H,9,10)(H,11,12)(H,13,14)
InChI KeyKBOJOGQFRVVWBH-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • N-acyl-alpha-amino acid
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • Imidazolyl carboxylic acid derivative
    • 

  • Azole
    • 

  • Imidazole
    • 

  • Acetamide
    • 

  • Heteroaromatic compound
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Azacycle
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.6ChemAxon
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area98.57 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.02 m³·mol⁻¹ChemAxon
Polarizability18.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Chai W, Wang L, Li T, Wang T, Wang X, Yan M, Zhu M, Gao J, Wang C, Ma Q, Qu H: Liquid Chromatography-Mass Spectrometry-Based Metabolomics Reveals Dynamic Metabolite Changes during Early Postmortem Aging of Donkey Meat. Foods. 2024 May 9;13(10):1466. doi: 10.3390/foods13101466. [PubMed:38790766  ] 
  2. Atunnise AK, Bodede O, Adewuyi A, Maharaj V, Prinsloo G, Salau BA: Metabolomics and in-vitro bioactivities studies of fermented Musa paradisiaca pulp: A potential alpha-amylase inhibitor. Heliyon. 2024 Jan 19;10(3):e24659. doi: 10.1016/j.heliyon.2024.e24659.  eCollection 2024 Feb 15. [PubMed:38317983  ] 
  3. Kim H, Shin J, Yang J, Sim Y, Yang JY: Biomarker Development for Identifying Mud Loach (Misgurnus mizolepis) Origin Country Using Untargeted Metabolite Profiling. Life (Basel). 2023 Oct 31;13(11):2149. doi: 10.3390/life13112149. [PubMed:38004289  ] 
  4. Xu J, Chen Q, Cai M, Han X, Lu H: Ultra-high performance liquid chromatography coupled to tandem mass spectrometry-based metabolomics study of diabetic distal symmetric polyneuropathy. J Diabetes Investig. 2023 Sep;14(9):1110-1120. doi: 10.1111/jdi.14041. Epub 2023  Jun 22. [PubMed:37347226  ] 
  5. Luo S, Surapaneni A, Zheng Z, Rhee EP, Coresh J, Hung AM, Nadkarni GN, Yu B, Boerwinkle E, Tin A, Arking DE, Steinbrenner I, Schlosser P, Kottgen A, Grams ME: NAT8 Variants, N-Acetylated Amino Acids, and Progression of CKD. Clin J Am Soc Nephrol. 2020 Dec 31;16(1):37-47. doi: 10.2215/CJN.08600520. [PubMed:33380473  ] 
  6. Cao M, Han Q, Zhang J, Zhang R, Wang J, Gu W, Kang W, Lian K, Ai L: An untargeted and pseudotargeted metabolomic combination approach to identify differential markers to distinguish live from dead pork meat by liquid chromatography-mass spectrometry. J Chromatogr A. 2020 Jan 11;1610:460553. doi: 10.1016/j.chroma.2019.460553. Epub  2019 Sep 17. [PubMed:31558272  ] 
  7. Razzano V, Paolino M, Reale A, Giuliani G, Donati A, Giorgi G, Artusi R, Caselli G, Visintin M, Makovec F, Battiato S, Samperi F, Villafiorita-Monteleone F, Botta C, Cappelli A: Poly-histidine grafting leading to fishbone-like architectures. RSC Adv. 2018 Feb 26;8(16):8638-8656. doi: 10.1039/c8ra00315g. eCollection 2018  Feb 23. [PubMed:35539867  ] 
  8. Jonassen T, Hamadi M, Remo SC, Waagbo R: An epidemiological study of cataracts in wild and farmed lumpfish (Cyclopterus lumpus L.) and the relation to nutrition. J Fish Dis. 2017 Dec;40(12):1903-1914. doi: 10.1111/jfd.12664. Epub 2017 Jun 29. [PubMed:28661002  ] 
  9. Roemeling MD, Williams J, Beckman JS, Hurst JK: Imidazole catalyzes chlorination by unreactive primary chloramines. Free Radic Biol Med. 2015 May;82:167-78. doi:  10.1016/j.freeradbiomed.2015.01.026. Epub 2015 Feb 4. [PubMed:25660996  ] 
  10. Liu Q, Bruns H, Schultze D, Xue Y, Zorn M, Flechtenmacher C, Straub BK, Rauen U, Schemmer P: HTK-N, a modified HTK solution, decreases preservation injury in a model of microsteatotic rat liver transplantation. Langenbecks Arch Surg. 2012 Dec;397(8):1323-31. doi: 10.1007/s00423-012-1022-9.  Epub 2012 Nov 1. [PubMed:23111581  ] 
  11. Wilbring M, Tugtekin SM, Zatschler B, Ebner A, Reichenspurner H, Kappert U, Matschke K, Deussen A: Preservation of endothelial vascular function of saphenous vein grafts after long-time storage with a recently developed potassium-chloride and N-acetylhistidine enriched storage solution. Thorac Cardiovasc Surg. 2013 Dec;61(8):656-62. doi: 10.1055/s-0032-1311549. Epub  2012 Jul 12. [PubMed:22791204  ] 
  12. Kao D, Chaintreau A, Lepoittevin JP, Gimenez-Arnau E: Synthesis of allylic hydroperoxides and EPR spin-trapping studies on the formation of radicals in iron systems as potential initiators of the sensitizing pathway. J Org Chem. 2011 Aug 5;76(15):6188-200. doi: 10.1021/jo200948x. Epub 2011 Jun 28. [PubMed:21648947  ] 
  13. Wilbring M, Tugtekin SM, Zatschler B, Ebner A, Reichenspurner H, Matschke K, Deussen A: Even short-time storage in physiological saline solution impairs endothelial vascular function of saphenous vein grafts. Eur J Cardiothorac Surg. 2011 Oct;40(4):811-5. doi: 10.1016/j.ejcts.2011.01.024.  Epub 2011 Mar 3. [PubMed:21376620  ] 
  14. Rhodes JD, Breck O, Waagbo R, Bjerkas E, Sanderson J: N-acetylhistidine, a novel osmolyte in the lens of Atlantic salmon (Salmo salar L.). Am J Physiol Regul Integr Comp Physiol. 2010 Oct;299(4):R1075-81. doi:  10.1152/ajpregu.00214.2010. Epub 2010 Jul 21. [PubMed:20660107  ] 
  15. Trosse C, Rhodes JD, Sanderson J, Breck O, Waagbo R: Effect of plant-based feed ingredients on osmoregulation in the Atlantic salmon lens. Comp Biochem Physiol B Biochem Mol Biol. 2010 Apr;155(4):354-62. doi:  10.1016/j.cbpb.2009.12.002. Epub 2009 Dec 31. [PubMed:20044022  ] 
  16. Annangudi SP, Deng Y, Gu X, Zhang W, Crabb JW, Salomon RG: Low-density lipoprotein has an enormous capacity to bind (E)-4-hydroxynon-2-enal (HNE): detection and characterization of lysyl and histidyl adducts containing multiple molecules of HNE. Chem Res Toxicol. 2008 Jul;21(7):1384-95. doi: 10.1021/tx8000303. Epub 2008 Jun  21. [PubMed:18570390  ] 
  17. Wille T, de Groot H, Rauen U: Improvement of the cold storage of blood vessels with a vascular preservation solution. Study in porcine aortic segments. J Vasc Surg. 2008 Feb;47(2):422-31. doi: 10.1016/j.jvs.2007.09.048. [PubMed:18164170  ] 
  18. Lu W, Uetrecht JP: Possible bioactivation pathways of lamotrigine. Drug Metab Dispos. 2007 Jul;35(7):1050-6. doi: 10.1124/dmd.107.015271. Epub 2007  Apr 4. [PubMed:17409271  ] 
  19. Jablonowska E, Palys B, Wagner-Wysiecka E, Jamrogiewicz M, Biernat JF, Bilewicz R: pH-tunable equilibria in azocrown ethers with histidine moieties. Bioelectrochemistry. 2007 Sep;71(1):99-106. doi:  10.1016/j.bioelechem.2006.09.005. Epub 2006 Sep 26. [PubMed:17081808  ]