NP-MRD: Showing NP-Card for N-Acetylhistidine (NP0333865)

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Record Information

Version

2.0

Created at

2024-09-09 21:01:01 UTC

Updated at

2024-09-09 21:01:01 UTC

NP-MRD ID

NP0333865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetylhistidine

Description

Constituent of the tissues of various fish and amphibian subspecies N-Acetylhistidine is found in fishes.

Structure

MOL SDF PDB SMILES InChI

  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

$$$$

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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈H₁₁N₃O₃

Average Mass

197.1940 Da

Monoisotopic Mass

197.08004 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not 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 Key

KBOJOGQFRVVWBH-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

histidine derivative (CHEBI:86910 )
a small molecule (CPD0-2016 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.6	ChemAxon
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	98.57 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.02 m³·mol⁻¹	ChemAxon
Polarizability	18.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing NP-Card for N-Acetylhistidine (NP0333865)

MOL for NP0333865 (N-Acetylhistidine)

3D MOL for NP0333865 (N-Acetylhistidine)

3D SDF for NP0333865 (N-Acetylhistidine)

3D-SDF for NP0333865 (N-Acetylhistidine)

PDB for NP0333865 (N-Acetylhistidine)

3D PDB for NP0333865 (N-Acetylhistidine)

SMILES for NP0333865 (N-Acetylhistidine)

INCHI for NP0333865 (N-Acetylhistidine)

Structure for NP0333865 (N-Acetylhistidine)

3D Structure for NP0333865 (N-Acetylhistidine)