N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide | CAS No. 120287-85-6

N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide

Basic Information

CAS Number

120287-85-6

Molecular Formula

C70H92ClN17O14

Molecular Weight

1431.06 g/mol

AD

Basic Physical Properties

CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CCCNC(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CN=CC=C3)NC(=O)C(CC4=CC=C(C=C4)Cl)NC(=O)C(CC5=CC6=CC=CC=C6C=C5)NC(=O)C

InChI

InChI=1S/C70H92ClN17O14/c1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+/m1/s1

InChIKey

SBNPWPIBESPSIF-MHWMIDJBSA-N

LogP

-0.5061300000000226

Topological Polar Surface Area

495.6699999999998 Ų

Hydrogen Bond Donor/Acceptor

20 / 31

Complexity

2840

Synonyms & References

English

  • SCHEMBL19712202
  • 130143-01-0
  • LHRH, N-acetyl-1-(3-(2-naphthyl)alanyl)-2-(4-chlorophenylalanyl)-3-(3-(3-pyridyl)alanyl)-6-citrulline-10-alanine-
  • SB 75
  • D-Alaninamide,N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N5-(aminocarbonyl)-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-
  • AC-28734
  • H01CC02
  • Cetrorelix [INN]
  • LHRH, N-Ac-1-Nal(2)-2-Phe(pCl)-3-Pal(3)-6-Cit-10-Ala-
  • CETRORELIX [WHO-DD]
  • N-acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-L-tyrosyl-N5-carbomoyl-D-ornithyl-L-leucyl-L-prolyl-D-alaninamide
  • HSDB 7696
  • UNII-OON1HFZ4BA
  • CETRORELIX [VANDF]
  • GTPL1190
  • DTXCID5020996
  • NS00078781
  • N-acetyl-3-(naphthalen-2-yl)-D-alanyl-4-chloro-D-phenylalanyl-3-(pyridin-3-yl)-D-alanyl-L-seryl-L-tyrosyl-N(5)-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide
  • HY-P0009
  • Ac-(D-Ala[3-(2-Naphthyl)])-[D-Phe(4-Cl)]-(D-Ala[3-(3-Pyridyl)])-Ser-Tyr-(D-Cit)-Leu-Arg-Pro-D-Ala-Oh
  • CHEMBL1200490
  • VEA28785
  • CHEBI:59224
  • CETRORELIX [HSDB]
  • BDBM50369965
  • Cetrorelix [INN:BAN]
  • 120287-85-6
  • Cetrotide (TN)
  • N-Acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N5-(aminocarbonyl)-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide
  • HS-2008
  • DB00050

MDL Number

MFCD00884467

FAQ

What are the physical and chemical properties of N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide (CAS: 120287-85-6)?

N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide is a crystalline compound with a high molecular weight. It has a high solubility in polar solvents such as dimethyl sulfoxide (DMSO) and low solubility in non-polar solvents. The compound is known for its reactivity, particularly in peptide bond formation and cleavage. It is also stable in acidic and basic conditions.

How is N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide (CAS: 120287-85-6) typically synthesized?

N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide is typically synthesized via solid-phase peptide synthesis (SPPS) methods. The synthesis involves the sequential addition of amino acid derivatives to a growing peptide chain using a suitable coupling agent and activation method. Commonly used coupling agents include HATU and DIC, with the coupling process being highly selective and yielding up to 95% purity.

What industries use N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide (CAS: 120287-85-6)?

N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide is primarily used in the pharmaceutical industry for the development of novel peptide-based therapeutics. It is also relevant in the polymer industry for the synthesis of functionalized peptides and in the field of sensors for its unique chemical reactivity.

What precautions should be taken when handling N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide (CAS: 120287-85-6)?

When handling N-Acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N~5~-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide, it is important to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat. Work should be conducted in a well-ventilated area or fume hood to minimize exposure. Spills should be cleaned up with appropriate absorbents and disposed of according to local regulations. Always consult the safety data sheet (SDS) for detailed handling and disposal procedures.

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