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20449-79-0 molecular structure
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(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}propanamido]-3-methylbutanamido]-4-methylpentanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]acetamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]-4-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-3-methylpentanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]pentanediamide

ChemBase ID: 106604
Molecular Formular: C131H229N39O31
Molecular Mass: 2846.46266
Monoisotopic Mass: 2844.75417174
SMILES and InChIs

SMILES:
CC[C@H](C)[C@H](NC(=O)CN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)N)C(=O)N
Canonical SMILES:
NCCCC[C@@H](C(=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)N1CCC[C@H]1C(=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[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[C@H](C(=O)N[C@H](C(=O)N)CCC(=O)N)CCC(=O)N)CCCNC(=N)N)CCCCN)CCCNC(=N)N)CCCCN)[C@H](CC)C)Cc1c[nH]c2c1cccc2)CO)[C@H](CC)C)CC(C)C)C)CC(C)C)[C@H](O)C)[C@H](O)C)CC(C)C)C(C)C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H]([C@H](CC)C)NC(=O)CN)C)CC(C)C
InChI:
InChI=1S/C131H229N39O31/c1-23-71(16)102(163-97(176)60-135)122(194)146-62-98(177)148-74(19)109(181)164-100(69(12)13)124(196)160-88(55-65(4)5)116(188)155-84(41-30-33-51-134)115(187)165-101(70(14)15)125(197)161-90(57-67(8)9)118(190)168-106(77(22)173)128(200)169-105(76(21)172)123(195)147-63-99(178)150-92(58-68(10)11)129(201)170-54-36-44-94(170)121(193)149-75(20)108(180)158-89(56-66(6)7)117(189)166-104(73(18)25-3)127(199)162-93(64-171)120(192)159-91(59-78-61-145-80-38-27-26-37-79(78)80)119(191)167-103(72(17)24-2)126(198)157-83(40-29-32-50-133)111(183)154-85(42-34-52-143-130(139)140)112(184)152-82(39-28-31-49-132)110(182)153-86(43-35-53-144-131(141)142)113(185)156-87(46-48-96(137)175)114(186)151-81(107(138)179)45-47-95(136)174/h26-27,37-38,61,65-77,81-94,100-106,145,171-173H,23-25,28-36,39-60,62-64,132-135H2,1-22H3,(H2,136,174)(H2,137,175)(H2,138,179)(H,146,194)(H,147,195)(H,148,177)(H,149,193)(H,150,178)(H,151,186)(H,152,184)(H,153,182)(H,154,183)(H,155,188)(H,156,185)(H,157,198)(H,158,180)(H,159,192)(H,160,196)(H,161,197)(H,162,199)(H,163,176)(H,164,181)(H,165,187)(H,166,189)(H,167,191)(H,168,190)(H,169,200)(H4,139,140,143)(H4,141,142,144)/t71-,72-,73-,74-,75-,76+,77+,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,100-,101-,102-,103-,104-,105-,106-/m0/s1
InChIKey:
VDXZNPDIRNWWCW-JFTDCZMZSA-N

Cite this record

CBID:106604 http://www.chembase.cn/molecule-106604.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}propanamido]-3-methylbutanamido]-4-methylpentanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]acetamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]-4-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-3-methylpentanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]pentanediamide
IUPAC Traditional name
(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-{2-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S,3S)-2-(2-aminoacetamido)-3-methylpentanamido]acetamido}propanamido]-3-methylbutanamido]-4-methylpentanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]acetamido}-4-methylpentanoyl]pyrrolidin-2-yl]formamido}propanamido]-4-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-(1H-indol-3-yl)propanamido]-3-methylpentanamido]hexanamido]-5-carbamimidamidopentanamido]hexanamido]-5-carbamimidamidopentanamido]-4-carbamoylbutanamido]pentanediamide
Synonyms
GIGAVLKVLTTGLPALISWIKRKRQQ-NH2
GIGAVLKVLTTGLPALISWIKRKRQQ-NH2 MELITTIN
Melittin
Melittin from honey bee venom
Melittin
CAS Number
20449-79-0
37231-28-0
EC Number
253-417-7
MDL Number
MFCD00076868
PubChem SID
24896718
24896910
162087302
PubChem CID
16133648
CHEMBL
412927
Chemspider ID
17290230
MeSH Name
Melitten
Wikipedia Title
Melittin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors 41  H Donor 41 
LogD (pH = 5.5) -26.697006  LogD (pH = 7.4) -23.742332 
Log P -10.533494  Molar Refractivity 755.6249 cm3
Polarizability 289.77097 Å3 Polar Surface Area 1152.34 Å2
Rotatable Bonds 97  Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Flash Point
112 °C expand Show data source
233.6 °F expand Show data source
RTECS
OS3960000 expand Show data source
OS3965000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
3462 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
1 expand Show data source
Risk Statements
21/22 expand Show data source
23/24/25 expand Show data source
Safety Statements
36 expand Show data source
36/37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H301-H311-H331 expand Show data source
H302-H312 expand Show data source
GHS Precautionary statements
P261-P280-P301 + P310-P311 expand Show data source
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 3462 6.1/PG 1 expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Gene Information
human ... ATP1A1(476), CALM1(801)mouse ... ATP1A1(11928), CALM1(12313)rat ... ATP1A1(24211), CALM1(24242) expand Show data source
Purity
~70% (HPLC) expand Show data source
≥85% (HPLC) expand Show data source
≥90% (HPLC) expand Show data source
≥97% (HPLC) expand Show data source
65-85% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
vial of 100 μg expand Show data source
Foreign Activity
Phospholipase A2 ≤0.5% expand Show data source
Phospholipase A2 ≤2% expand Show data source
Empirical Formula (Hill Notation)
C131H229N39O31 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - M2272 external link
Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.
Sigma Aldrich - M4171 external link
Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.
Sigma Aldrich - M1407 external link
Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.
Preparation Note
HPLC-purified and use tested as a protease substrate.
Sigma Aldrich - M7391 external link
Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.
Sigma Aldrich - 63650 external link
Amino Acid Sequence
Gly-Ile-Gly-Ala-Val-Leu-Lys-Val-Leu-Thr-Thr-Gly-Leu-Pro-Ala-Leu-Ile-Ser-Trp-Ile-Lys-Arg-Lys-Arg-Gln-Gln-NH2
Biochem/physiol Actions
Binds calmodulin in a Ca2+-dependent manner; inhibits Na+-K+-ATPase.
Other Notes
The principle hemolytic component of honeybee venom.
Main component of the honeybee venom. It is a basic hydrophobic peptide which alters membrane permeability1; Interference with enzymes2; Interaction with calmodulin3; Used in the affinity chromatographic purification of calmodulin4

REFERENCES

REFERENCES

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PATENTS

PATENTS

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