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129696-25-9 molecular structure
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(4R)-4-{2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R)-2-[(2R)-6-amino-2-[(2R)-6-amino-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R,3R)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]hexanamido]hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}-4-{[(1R,2R)-1-{[(1R)-1-{[(1R)-2-carbamoyl-1-{[(1R)-1-carbamoyl-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid

ChemBase ID: 131007
Molecular Formular: C114H181N31O28S
Molecular Mass: 2465.91284
Monoisotopic Mass: 2464.34130531
SMILES and InChIs

SMILES:
CC[C@@H](C)[C@H](C(=O)NCC(=O)N[C@H](CCCCN)C(=O)N[C@H](Cc1ccccc1)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](Cc1c[nH]cn1)C(=O)N[C@H](CO)C(=O)N[C@H](C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](Cc1ccccc1)C(=O)NCC(=O)N[C@H](CCCCN)C(=O)N[C@H](C)C(=O)N[C@H](Cc1ccccc1)C(=O)N[C@H](C(C)C)C(=O)NCC(=O)N[C@H](CCC(=O)O)C(=O)N[C@H]([C@H](C)CC)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(=O)N)C(=O)N[C@H](CO)C(=O)N)NC(=O)CN
Canonical SMILES:
NCCCC[C@H](C(=O)N[C@@H](C(=O)NCC(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)NCC(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N)CO)CC(=O)N)CCSC)[C@@H](CC)C)CCC(=O)O)C(C)C)Cc1ccccc1)C)CCCCN)Cc1ccccc1)NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H]([C@@H](CC)C)NC(=O)CN)CCCCN)Cc1ccccc1)CC(C)C)Cc1nc[nH]c1)CO)C)CCCCN
InChI:
InChI=1S/C114H181N31O28S/c1-12-65(7)94(143-88(149)55-119)113(172)125-59-90(151)130-74(38-24-28-45-116)101(160)138-81(51-70-33-19-15-20-34-70)107(166)136-79(49-63(3)4)106(165)139-83(53-72-56-122-62-126-72)108(167)142-86(61-147)111(170)128-67(9)97(156)132-75(39-25-29-46-117)102(161)133-76(40-26-30-47-118)103(162)137-80(50-69-31-17-14-18-32-69)99(158)123-57-89(150)129-73(37-23-27-44-115)100(159)127-68(10)98(157)135-82(52-71-35-21-16-22-36-71)110(169)144-93(64(5)6)112(171)124-58-91(152)131-77(41-42-92(153)154)105(164)145-95(66(8)13-2)114(173)134-78(43-48-174-11)104(163)140-84(54-87(120)148)109(168)141-85(60-146)96(121)155/h14-22,31-36,56,62-68,73-86,93-95,146-147H,12-13,23-30,37-55,57-61,115-119H2,1-11H3,(H2,120,148)(H2,121,155)(H,122,126)(H,123,158)(H,124,171)(H,125,172)(H,127,159)(H,128,170)(H,129,150)(H,130,151)(H,131,152)(H,132,156)(H,133,161)(H,134,173)(H,135,157)(H,136,166)(H,137,162)(H,138,160)(H,139,165)(H,140,163)(H,141,168)(H,142,167)(H,143,149)(H,144,169)(H,145,164)(H,153,154)/t65-,66-,67-,68-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,93-,94-,95-/m1/s1
InChIKey:
VBHOTDXAQOWLHQ-ONJVDTHJSA-N

Cite this record

CBID:131007 http://www.chembase.cn/molecule-131007.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4R)-4-{2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R)-2-[(2R)-6-amino-2-[(2R)-6-amino-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R,3R)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]hexanamido]hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}-4-{[(1R,2R)-1-{[(1R)-1-{[(1R)-2-carbamoyl-1-{[(1R)-1-carbamoyl-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
IUPAC Traditional name
(4R)-4-{2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R)-2-[(2R)-6-amino-2-[(2R)-6-amino-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-2-[(2R)-6-amino-2-{2-[(2R,3R)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]hexanamido]hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}-4-{[(1R,2R)-1-{[(1R)-1-{[(1R)-2-carbamoyl-1-{[(1R)-1-carbamoyl-2-hydroxyethyl]carbamoyl}ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}butanoic acid
Synonyms
D-Magainin II amide
CAS Number
129696-25-9
PubChem SID
162225285
PubChem CID
71308376

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
M8535 external link Add to cart Please log in.
Data Source Data ID
PubChem 71308376 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.609873  H Acceptors 34 
H Donor 33  LogD (pH = 5.5) -24.266697 
LogD (pH = 7.4) -20.235832  Log P -12.620802 
Molar Refractivity 633.675 cm3 Polarizability 249.21127 Å3
Polar Surface Area 962.92 Å2 Rotatable Bonds 86 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Compostion
Peptide content, ~70% expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - M8535 external link
Application
The all-D maganin peptides were resistant to enzymatic degradation and caused equivalent amounts of electrical conductivity when tested in planar lipid bilayers. The D enantiomers were equally active against representative Gram-negative and Gram-positive species.
Biochem/physiol Actions
Antibiotic peptide. Thought to preferentially bind to anionic phospholipids abundant in bacterial membranes with the formation of dynamic peptide-lipid supramolecular pore and cell permeabilization, magainins are positively charged and amphiphatic. Binding to artificial neutral membranes has also been demonstrated.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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