ChemFOnt: Showing chemical card for 2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine (CFc000007234)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:27 UTC

Chemfont ID

CFc000007234

Molecule Identification

Common Name

2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine

Definition

2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine is an unusual amino acid that results from the post-translational modification of histidine in certain proteins. In particular, it is a post-translational derivative of histidine that exists in protein synthesis elongation factor 2 (EF2) at the site of diphtheria toxin-catalyzed ADP-ribosylation of elongation factor 2. It is a precursor for diphthamide. This compound is a substrate for the enzyme diphthine synthase (EC 2.1.1.98). This enzyme catalyzes the chemical reaction: S-adenosyl-L-methionine + 2-(3-carboxy-3-aminopropyl)-L-histidine = S-adenosyl-L-homocysteine + 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
EF-2 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine	ChEBI
Elongation factor 2 2-[3-carboxy-3-(methylammonio)propyl]-L-histidine	ChEBI
1-Carboxy-3-(L-histidin-2-yl)-N-methylpropan-1-aminium	HMDB
2-[3-Carboxy-3-(methylammonio)propyl]-his	HMDB
2-[3-Carboxy-3-(methylammonio)propyl]-histidine	HMDB
[3-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]]-1-carboxy- propyl]-methyl-ammonium	HMDB

Chemical Formula

C₁₁H₁₉N₄O₄

Average Molecular Weight

271.293

Monoisotopic Molecular Weight

271.140630116

IUPAC Name

(3-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}-1-carboxypropyl)(methyl)azanium

Traditional Name

(3-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}-1-carboxypropyl)(methyl)azanium

CAS Registry Number

None

SMILES

C[NH2+]C(CCC1=NC=C(C[C@H](N)C(O)=O)N1)C(O)=O

InChI Identifier

InChI=1S/C11H18N4O4/c1-13-8(11(18)19)2-3-9-14-5-6(15-9)4-7(12)10(16)17/h5,7-8,13H,2-4,12H2,1H3,(H,14,15)(H,16,17)(H,18,19)/p+1/t7-,8?/m0/s1

InChI Key

YBMOTEQVMANKGX-JAMMHHFISA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives 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
Alpha-amino acid
L-alpha-amino acid
Aralkylamine
Dicarboxylic acid or derivatives
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Organoheterocyclic compound
Azacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Amine
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ammonium ion (CHEBI:16475 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0011654)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.2 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-6.3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.42	ChemAxon
pKa (Strongest Basic)	10.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	77.33 m³·mol⁻¹	ChemAxon
Polarizability	27.91 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

HMDB0011654

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028345

KNApSAcK ID

Not Available

Chemspider ID

389379

KEGG Compound ID

C04692

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440443

PDB ID

Not Available

ChEBI ID

16475

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine (CFc000007234)

MOL for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

3D MOL for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

3D SDF for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

3D-SDF for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

PDB for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

3D PDB for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

SMILES for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

INCHI for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

Structure for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)

3D Structure for CFc000007234 (2-(3-Carboxy-3-(methylammonio)propyl)-L-histidine)