ContaminantDB: L,L-Cyclo(histidylprolyl)

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:39:20 UTC

Update Date

2016-11-09 01:21:17 UTC

Accession Number

CHEM035313

Identification

Common Name

L,L-Cyclo(histidylprolyl)

Class

Small Molecule

Description

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
His-pro-DKP	MeSH
Cyclo(his-pro)	MeSH
Cyclo(histidyl-prolyl)	MeSH
Histidyl-proline diketopiperazine	MeSH
Histidyl-proline diketopiperazine, (3R-cis)-isomer	MeSH
Histidyl-proline diketopiperazine, (3S-cis)-isomer	MeSH
Histidyl-proline diketopiperazine, (3S-trans)-isomer	MeSH
Histidyl-proline-diketopiperazine	MeSH

Chemical Formula

C₁₂H₁₆N₄O₂

Average Molecular Mass

248.281 g/mol

Monoisotopic Mass

248.127 g/mol

CAS Registry Number

53109-32-3

IUPAC Name

(3S,9aS)-3-(1H-imidazol-5-ylmethyl)-octahydro-1H-pyrido[1,2-a]piperazine-1,4-dione

Traditional Name

(3S,9aS)-3-(3H-imidazol-4-ylmethyl)-hexahydro-2H-pyrido[1,2-a]piperazine-1,4-dione

SMILES

[H][C@@]12CCCCN1C(=O)[C@H](CC1=CN=CN1)NC2=O

InChI Identifier

InChI=1S/C12H16N4O2/c17-11-10-3-1-2-4-16(10)12(18)9(15-11)5-8-6-13-7-14-8/h6-7,9-10H,1-5H2,(H,13,14)(H,15,17)/t9-,10-/m0/s1

InChI Key

LCXWQHWWTPOAFI-UWVGGRQHSA-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
Piperidine
Azole
Imidazole
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Heteroaromatic compound
Lactam
Carboxamide group
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	9.12 g/L	ALOGPS
logP	-0.36	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	10.95	ChemAxon
pKa (Strongest Basic)	6.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.45 m³·mol⁻¹	ChemAxon
Polarizability	24.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0c10-8960000000-b59521a7bf7f2dbcd98b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-843d3723786addf5c81b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-0090000000-38a066bbd349061998cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-98e8fd70b7c52af6ad80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0190000000-1981c342d35a74baaaf5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-8940000000-df121bc941f701b83e43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9400000000-bb22aeb05ef45a82e903	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-2d6df444943bd8abf9e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-7a61131b9929146e0cc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000t-9560000000-d98006bfa210732b955f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-9825da4495af4eed0ee2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1290000000-03e21d76de28525b9ad9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9410000000-f6ed33b9456dfc589d83	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002053

FooDB ID

FDB022818

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

58646

ChEBI ID

90039

PubChem Compound ID

65137

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Ma, Yaping; Bai, Wei; Zhong, Fei; Cui, Xueyun. Method for the preparation of all stereoisomers of cyclo(histidylproline). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 11pp.

2. Leduque P, Jackson IM, Kervran A, Aratan-Spire S, Czernichow P, Dubois PM: Histidyl-proline diketopiperazine (His-Pro DKP) immunoreactivity is present in the glucagon-containing cells of the human fetal pancreas. J Clin Invest. 1987 Mar;79(3):875-80.

3. Takahara Y, Battaini F, Ross DD, Akman SA, Bachur NR, Bailey KR, Lakatos E, Peterkofsky A: Detection in human serum by radioimmunoassay of histidyl-proline diketopiperazine, a metabolite of thyrotropin-releasing hormone. J Clin Endocrinol Metab. 1983 Feb;56(2):312-9.

L,L-Cyclo(histidylprolyl) (CHEM035313)

Structure for CHEM035313: L,L-Cyclo(histidylprolyl)