ChemFOnt: Showing chemical card for 2-(3-Carboxy-3-aminopropyl)-L-histidine (CFc000007235)

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

CFc000007235

Molecule Identification

Common Name

2-(3-Carboxy-3-aminopropyl)-L-histidine

Definition

2-(3-Carboxy-3-aminopropyl)-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
2-(3-Carboxy-3-aminopropyl)-L-histidine	ChEBI
2-(3-amino-3-Carboxypropyl)-L-histidine	HMDB
2-amino-4-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]] butanoate	HMDB
2-amino-4-[[4-(2-amino-2-Carboxy-ethyl)-1H-imidazol-2-yl]] butanoic acid	HMDB

Chemical Formula

C₁₀H₁₆N₄O₄

Average Molecular Weight

256.2584

Monoisotopic Molecular Weight

256.11715502

IUPAC Name

2-amino-4-{5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl}butanoic acid

Traditional Name

2-amino-4-{4-[(2S)-2-amino-2-carboxyethyl]-3H-imidazol-2-yl}butanoic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C10H16N4O4/c11-6(9(15)16)1-2-8-13-4-5(14-8)3-7(12)10(17)18/h4,6-7H,1-3,11-12H2,(H,13,14)(H,15,16)(H,17,18)/t6?,7-/m0/s1

InChI Key

CJCSNWWKPUXVRD-MLWJPKLSSA-N

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
Imidazolyl carboxylic acid derivative
Aralkylamine
Dicarboxylic acid or derivatives
Azole
Imidazole
Heteroaromatic compound
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:17144 )
L-histidine derivative (CHEBI:17144 )

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0011655)

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	8.71 g/L	ALOGPS
logP	-4.1	ALOGPS
logP	-6.5	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.63	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	61.14 m³·mol⁻¹	ChemAxon
Polarizability	25.54 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