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108433-99-4 molecular structure
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(4S)-4-{[(1S,2S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}pentyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}-4-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]acetamido}hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}butanoic acid

ChemBase ID: 133801
Molecular Formular: C112H177N29O28S
Molecular Mass: 2409.84628
Monoisotopic Mass: 2408.30385717
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)NCC(=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](CCCCN)C(=O)N[C@@H](CO)C(=O)O)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)O)CO)CCCCN)CCSC)[C@H](CC)C)CCC(=O)O)C(C)C)Cc1ccccc1)C)CCCCN)Cc1ccccc1)NC(=O)CNC(=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
InChI:
InChI=1S/C112H177N29O28S/c1-12-65(7)93(139-86(144)54-117)110(166)122-59-89(147)128-75(39-25-29-46-115)100(156)135-81(51-70-33-19-15-20-34-70)105(161)133-79(49-63(3)4)104(160)136-83(53-72-55-118-62-123-72)106(162)137-84(60-142)108(164)124-67(9)95(151)119-56-87(145)127-74(38-24-28-45-114)99(155)134-80(50-69-31-17-14-18-32-69)97(153)120-57-88(146)126-73(37-23-27-44-113)98(154)125-68(10)96(152)132-82(52-71-35-21-16-22-36-71)107(163)140-92(64(5)6)109(165)121-58-90(148)129-77(41-42-91(149)150)103(159)141-94(66(8)13-2)111(167)131-78(43-48-170-11)102(158)130-76(40-26-30-47-116)101(157)138-85(61-143)112(168)169/h14-22,31-36,55,62-68,73-85,92-94,142-143H,12-13,23-30,37-54,56-61,113-117H2,1-11H3,(H,118,123)(H,119,151)(H,120,153)(H,121,165)(H,122,166)(H,124,164)(H,125,154)(H,126,146)(H,127,145)(H,128,147)(H,129,148)(H,130,158)(H,131,167)(H,132,152)(H,133,161)(H,134,155)(H,135,156)(H,136,160)(H,137,162)(H,138,157)(H,139,144)(H,140,163)(H,141,159)(H,149,150)(H,168,169)/t65-,66-,67-,68-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,92-,93-,94-/m0/s1
InChIKey:
OFIZOVDANLLTQD-ZVNXOKPXSA-N

Cite this record

CBID:133801 http://www.chembase.cn/molecule-133801.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4S)-4-{[(1S,2S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}pentyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}-4-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]acetamido}hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}butanoic acid
IUPAC Traditional name
(4S)-4-{[(1S,2S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}pentyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-2-methylbutyl]carbamoyl}-4-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-hydroxypropanamido]propanamido]acetamido}hexanamido]-3-phenylpropanamido]acetamido}hexanamido]propanamido]-3-phenylpropanamido]-3-methylbutanamido]acetamido}butanoic acid
Synonyms
Magainin I
CAS Number
108433-99-4
MDL Number
MFCD00133521
PubChem SID
162228078
PubChem CID
44350363

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
M7152 external link Add to cart Please log in.
Data Source Data ID
PubChem 44350363 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.1285455  H Acceptors 34 
H Donor 32  LogD (pH = 5.5) -21.811525 
LogD (pH = 7.4) -18.026985  Log P -13.197715 
Molar Refractivity 619.5013 cm3 Polarizability 243.60574 Å3
Polar Surface Area 914.04 Å2 Rotatable Bonds 84 
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
Purity
≥97% (HPLC) expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - M7152 external link
Amino Acid Sequence
Gly-Ile-Gly-Lys-Phe-Leu-His-Ser-Ala-Gly-Lys-Phe-Gly-Lys-Ala-Phe-Val-Gly-Glu-Ile-Met-Lys-Ser
Application
Initial sites of magainin I binding to E. coli have been shown to be lipopolysaccharide.
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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