Basic information
- CAS
53109-32-3- Standard SMILES
O=C1N[C@@H](Cc2cnc[nH]2)C(=O)N2CCC[C@@H]12- InChIKey
NAKUGCPAQTUSBE-IUCAKERBSA-N- Molecular formula
- C11H14N4O2
- Average molar mass
- 234.25 g/mol
- Monoisotopic mass
- 234.1116757
Overview
Cyclo(L-His-L-Pro) is a homodetic cyclic peptide resulting from the formal condensation of both the amino and acid groups of L-histidine with the acid and amino groups of L-proline. It is a metabolite of thyrotropin-releasing hormone (TRH). It has a role as a dopamine uptake inhibitor, an anti-inflammatory agent and a human blood serum metabolite. It is a homodetic cyclic peptide, a member of imidazoles, a dipeptide and a pyrrolopyrazine. It is functionally related to a L-histidine and a L-proline.
Names & identifiers
- Preferred name
- Cyclo(his-pro)
- IUPAC
- (3S,8aS)-3-(1H-imidazol-5-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
- English name
- Cyclo(-His-Pro)
- Molecular formula
- C11H14N4O2
- Molecular weight
- 234.25
Names & synonyms
Cyclo(his-pro)53109-32-3Cyclo(L-His-L-Pro)UNII-Q10817UXVTQ10817UXVTL-His-L-Pro-DKPL,L-cyclo(histidylprolyl)CHEBI:90039(3S,8aS)-3-(1H-Imidazol-4-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(3S,8aS)-3-[(1H-imidazol-5-yl)methyl]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione(3S,8AS)-3-(1H-IMIDAZOL-5-YLMETHYL)-2,3,6,7,8,8A-HEXAHYDROPYRROLO(1,2-A)PYRAZINE-1,4-DIONE(3S,8aS)-3-(1H-imidazol-5-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Show more names
Histidylproline diketopiperazineCyclo(HP)c(His-Pro)Cyclo(Pro-His)HIS-PRO, CYCLICCyclo-Pro-His-HOCYCLO(HIS-PRO), >99%Vitamin B6 Impurity 93Cyclo(histidyl-proline)
(3S,8aS)-3-((1H-imidazol-5-yl)methyl)-octahydropyrrolo(1,2-a)pyrazine-1,4-dione(3S,8aS)-3-((1H-imidazol-5-yl)methyl)hexahydropyrrolo(1,2-a)pyrazine-1,4-dione(3S,8aS)-3-(1H-Imidazol-4-ylmethyl)hexahydropyrrolo(1,2-a)pyrazine-1,4-dione(3S,8aS)-3-[(1H-imidazol-5-yl)methyl]-octahydropyrrolo[1,2-a]pyrazine-1,4-dioneRefChem:129278Cyclo(-His-Pro)Protirelin EP Impurity EMFCD00133207
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 78.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 346
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 162 · 162—164 °C
- Boiling point
- 659.3 · 659.3±48.0 °C(Predicted)
- Density
- 1.41 · 1.41±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 1 mg/ml; · DMF: 1 mg/ml; DMSO: 1 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 1 mg/ml
- pka
- 12.73 · 12.73±0.40(Predicted)
- form
- solid
- color
- Light yellow to yellow
- Cosmetics Ingredients Functions
- HUMECTANTANTIOXIDANTSKIN CONDITIONING - MISCELLANEOUSPRESERVATIVESKIN PROTECTING
- InChI
- 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
- InChIKey
- NAKUGCPAQTUSBE-IUCAKERBSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
UsesCyclo(L-histidyl-L-proline) is used in the pharmaceutical composition comprising cyclo(His-Pro) for preventing or treating obesity.
Suppliers60 total
LIDE PHARMACEUTICALS LIMITED+852-55945652 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
湖北强耀生物科技有限公司18301728382 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
南京昱盛康生物科技有限公司13327808530 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
南通先行生物医药科技有限公司513-85982855 18921614129 · [email protected]
Aladdin Scientific[email protected]
上海鸿肽生物科技有限公司15318089928 · [email protected]
中科华药(江苏)生物科技有限公司18020125070 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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