CAERULEIN CAS#: 17650-98-5; 凯望编码 (ChemWhat Code): 98454

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名CAERULEIN
IUPAC Name(3S)-3-[[(2S)-5-amino-5-oxo-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-[[(2S)-1-[[(2S,3R)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid  
分子结构CAERULEIN-CAS-17650-98-5
CAS编号 17650-98-5
MDL NumberMFCD00076478
别名Caerulein
Ceruletide
17650-98-5
Cerulein
Ceruletida
Ceruletidum
5-Oxo-L-prolyl-L-glutaminyl-L-alpha-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamide
5-Oxo-L-prolyl-L-glutaminyl-L-aspartyl-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-L-alaninamide 4-(hydrogen sulfate) (ester)
CHEBI:59219
Caerulein (~85%)
888Y08971B
Ceruletidum [INN-Latin]
Ceruletida [INN-Spanish]
Ceruletide [USAN:INN:BAN]
(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid
5-oxo-L-prolyl-L-glutaminyl-L-a-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-a-aspartyl-L-phenylalaninamide
CCRIS 3063
Ceruletide (USAN/INN)
UNII-888Y08971B
Caerulein, sulfated
MFCD00076478
CERULETIDE [MI]
CERULETIDE [INN]
CERULETIDE [USAN]
CERULETIDE [MART.]
CERULETIDE [WHO-DD]
SCHEMBL29520
GTPL7589
CHEMBL1201355
DTXSID8040434
YRALAIOMGQZKOW-HYAOXDFASA-N
HY-A0190
AKOS030529560
CS-5876
DB00403
AS-56061
NS00004791
C73362
D03442
EN300-23248418
Q5065299
pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2
(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid
5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE
分子式C58H73N13O21S2
分子量1352.4
InChIInChI=1S/C58H73N13O21S2/c1-29(72)49(71-57(87)40(23-31-12-14-33(15-13-31)92-94(89,90)91)68-56(86)43(26-48(78)79)69-52(82)37(16-18-44(59)73)65-51(81)36-17-19-45(74)63-36)58(88)62-28-46(75)64-41(24-32-27-61-35-11-7-6-10-34(32)35)54(84)66-38(20-21-93-2)53(83)70-42(25-47(76)77)55(85)67-39(50(60)80)22-30-8-4-3-5-9-30/h3-15,27,29,36-43,49,61,72H,16-26,28H2,1-2H3,(H2,59,73)(H2,60,80)(H,62,88)(H,63,74)(H,64,75)(H,65,81)(H,66,84)(H,67,85)(H,68,86)(H,69,82)(H,70,83)(H,71,87)(H,76,77)(H,78,79)(H,89,90,91)/t29-,36+,37+,38+,39+,40+,41+,42+,43+,49+/m1/s1
InChI KeyYRALAIOMGQZKOW-HYAOXDFASA-N
Isomeric SMILESC[C@H]([C@@H](C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]5CCC(=O)N5)O 
Patent Information
Patent IDTitlePublication Date
US4351829Use of polypeptides as analgesic drugs1982

Physical Data

AppearanceWhite Powder

Spectra

No data available

Route of Synthesis (ROS)

Route of Synthesis (ROS) of CAERULEIN CAS 17650-98-5
Route of Synthesis (ROS) of CAERULEIN CAS 17650-98-5
ConditionsYield

Experimental Procedure
XIII N-terminal tetrapeptide sulfate ester hydrazide of CRL
butyl ester and coupled with DCC to the Tyr-sulfate ester-resin. After deblocking with 50% TFA/CH2 Cl2 (v/v), BOC-Glu(p-nitrophenyl ester) and pGlu(pentafluorophenyl ester) are respectively used for stepwise coupling. The tetrapeptide sulfate ester is cleaved from the resin in DMF with 30-fold excess hydrazine and isolated by precipitation with ethyl ether. It is further purified by precipitation from DMF with ethylacetate, yielding a pure Caerulein 1-4 tetrapeptide hydrazide suitable for further synthesis.

Safety and Hazards

GHS Hazard StatementsNot Classified

Source: European Chemicals Agency (ECHA)
License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
License URL: https://echa.europa.eu/web/guest/legal-notice
Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446
Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database

Other Data

TransportationStore at -20°C for long time, in container tightly sealed; Protect from light.
HS Code
StorageStore at -20°C for long time, in container tightly sealed; Protect from light.
Shelf Life2 years
Market Price
Druglikeness
Lipinski rules component
分子量1352.42
logP-5.328
HBA33
HBD17
Matching Lipinski Rules1
Veber rules component
Polar Surface Area (PSA)585.08
Rotatable Bond (RotB)47
Matching Veber Rules0
Use Pattern
Frogletin (also known as Frog Dermaseptin) is a type of antimicrobial peptide extracted from frog skin, with a variety of biological activities. Its main functions include:
Antimicrobial Activity: Frogletin has significant inhibitory or killing effects on various pathogens, including bacteria, fungi, and viruses. This gives it potential applications in fighting infections, especially those caused by multidrug-resistant bacteria.
Antitumor Activity: Some studies have shown that Frogletin peptides can selectively kill certain cancer cells without significantly harming normal cells, making it a promising candidate for cancer treatment.
Immune Modulation: Frogletin has the potential to regulate immune responses by stimulating or suppressing immune cell activity, enhancing the body’s defense against infections and diseases.
Anti-inflammatory Effects: In certain cases, Frogletin exhibits anti-inflammatory properties, helping to reduce inflammation caused by infections or immune reactions.

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