ChemFOnt: Showing chemical card for Cyclo(Leu-Phe) (CFc000075083)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 20:37:19 UTC

Chemfont ID

CFc000075083

Molecule Identification

Common Name

Cyclo(Leu-Phe)

Definition

Cyclo(leu-phe), also known as cyclo(Phe-leu) or cFL, is classified as an alpha amino acid or an Alpha amino acid derivative. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Cyclo(leu-phe) is considered to be a practically insoluble (in water) and a moderately acidic compound. Cyclo(leu-phe) can be found in feces.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3S,6S)-3-(2-Methylpropyl)-6-(phenylmethyl)-2,5-piperazinedione	ChEBI
cFL	ChEBI
Cyclo(L-leu-L-phe)	ChEBI
Cyclo(L-leucyl-L-phenylalanyl)	ChEBI
Cyclo(L-phe-L-leu)	ChEBI
Cyclo(phe-leu)	ChEBI
L-Phenylalanyl-L-leucine diketopiperazine	ChEBI
(3S,6S)-3-Benzyl-6-(2-methylpropyl)piperazine-2,5-dione	Kegg
Cyclo(leucyl-phenylalanyl)	HMDB
cyclo(Leu-phe)	ChEBI

Chemical Formula

C₁₅H₂₀N₂O₂

Average Molecular Weight

260.337

Monoisotopic Molecular Weight

260.152477892

IUPAC Name

(3S,6S)-3-benzyl-6-(2-methylpropyl)-3,6-dihydropyrazine-2,5-diol

Traditional Name

(3S,6S)-3-benzyl-6-(2-methylpropyl)-3,6-dihydropyrazine-2,5-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC(C)C)N=C(O)[C@]([H])(CC2=CC=CC=C2)N=C1O

InChI Identifier

InChI=1S/C15H20N2O2/c1-10(2)8-12-14(18)17-13(15(19)16-12)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9H2,1-2H3,(H,16,19)(H,17,18)/t12-,13-/m0/s1

InChI Key

QPDMOMIYLJMOQJ-STQMWFEESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Benzenoid
Secondary carboxylic acid amide
Lactam
Carboxamide group
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

2,5-diketopiperazines (CHEBI:71608 )

Functional Ontology

Not Available

Feces (PMID: 27275383)

Source

Exogenous

Exogenous (HMDB: HMDB0094673)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.097 g/L	ALOGPS
logP	2.36	ALOGPS
logP	1.76	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	4.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.93 m³·mol⁻¹	ChemAxon
Polarizability	28.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0094673

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5429202

KEGG Compound ID

C20519

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7076347

PDB ID

Not Available

ChEBI ID

71608

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cyclo(Leu-Phe) (CFc000075083)

MOL for CFc000075083 (Cyclo(Leu-Phe))

3D MOL for CFc000075083 (Cyclo(Leu-Phe))

3D SDF for CFc000075083 (Cyclo(Leu-Phe))

3D-SDF for CFc000075083 (Cyclo(Leu-Phe))

PDB for CFc000075083 (Cyclo(Leu-Phe))

3D PDB for CFc000075083 (Cyclo(Leu-Phe))

SMILES for CFc000075083 (Cyclo(Leu-Phe))

INCHI for CFc000075083 (Cyclo(Leu-Phe))

Structure for CFc000075083 (Cyclo(Leu-Phe))

3D Structure for CFc000075083 (Cyclo(Leu-Phe))