Cyclo(-His-Pro) - ≥98% , CAS No.53109-32-3

CAS: 53109-32-3 Cat. No.: C339850 Formula: C₁₁H₁₄N₄O₂ Molecular Weight: 234.26

GRADE & PURITY ≥98%

Synonyms

Cyclo(his-pro)|Histidylproline diketopiperazine|Cyclo(L-histidyl-L-proline)|Histidylproline dioxopiperazine|Cyclo(histidyl-proline)|Cyclo(prolylhistidine)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Cyclo(his-pro) (Cyclo(histidyl-proline)) is an orally active cyclic dipeptide structurally related to tyreotropin-releasing hormone. Cyclo(his-pro) could inhibit NF-κB nuclear accumulation. Cyclo(his-pro) can cross the brain-blood-barrier and affect diverse inflammatory and stress responses. 

Application：

Cyclo(L-His-L-Pro) is a versatile molecule and it finds application in biochemical and metabolomics research.

Specifications

Synonyms

Cyclo(his-pro) | Histidylproline diketopiperazine | Cyclo(L-histidyl-L-proline) | Histidylproline dioxopiperazine | Cyclo(histidyl-proline) | Cyclo(prolylhistidine)

Specifications & Purity

≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

Pubchem Sid

528763958

Canonical Smiles

C1CC2C(=O)NC(C(=O)N2C1)CC3=CN=CN3

IUPAC Name

(3S,8aS)-3-(1H-imidazol-5-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

InChIKey

NAKUGCPAQTUSBE-IUCAKERBSA-N

INCHI

1S/C11H14N4O2/c16-10-9-2-1-3-15(9)11(17)8(14-10)4-7-5-12-6-13-7/h5-6,8-9H,1-4H2,(H,12,13)(H,14,16)/t8-,9-/m0/s1

Isomeric SMILES

C1C[C@H]2C(=O)N[C@H](C(=O)N2C1)CC3=CN=CN3

WGK Germany

3

Molecular Weight

234.26

Reaxy-Rn

3558939

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3558939&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: 2,5-dioxopiperazines N-alkylpiperazines Tertiary carboxylic acid amides Pyrrolidines Imidazoles Heteroaromatic compounds Secondary carboxylic acid amides Lactams Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-amino acid or derivatives - Dioxopiperazine - 2,5-dioxopiperazine - N-alkylpiperazine - 1,4-diazinane - Piperazine - Azole - Imidazole - Pyrrolidine - Tertiary carboxylic acid amide - Heteroaromatic compound - Secondary carboxylic acid amide - Lactam - Carboxamide group - Organoheterocyclic compound - Azacycle - Organic nitrogen compound - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound 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.
• External Descriptors: imidazoles - pyrrolopyrazine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

HepG2 (196354 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SMN1 Tchem Survival motor neuron protein (34246 Activities)

Discover Target: SMN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Saccharomyces cerevisiae (19171 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasmodium falciparum (966862 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (Miscible).
• x_refractive_index: n20D~1.63 (Predicted)
• x_specific_rotation: +54.8° to +55.5°(c=10 in 0.2 ml 6N NH4OH/100 ml H2O)
• x_boil_point_char: 744.8° C at 760 mmHg
• x_melt_point_char: 165-170° C
• Molecular Weight: 234.250 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 234.112 Da
• Monoisotopic Mass: 234.112 Da
• Topological Polar Surface Area: 78.100 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 346.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1