(4S)-4-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-methylpentanamido]propanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]-5-[(2S)-2-[(2S)-2-{[(1S,2S)-1-{[(1S,2S)-1-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}butyl]carbamoyl}-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-5-oxopentanoic acid

• ChemBase ID: 131390
• Molecular Formular: C106H184N28O30
• Molecular Mass: 2330.76476
• Monoisotopic Mass: 2329.37331663
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CO)NC(=O)[C@H](CCC(=O)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)N[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=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)O)CCCNC(=N)N)CCCNC(=N)N)C(C)C)[C@H](O)C)[C@H](CC)C)[C@H](CC)C)CCC(=O)O)[C@H](O)C)[C@H](O)C)CC(C)C)C(C)C)NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](CCC(=O)O)N)CO)CC(C)C)C
• InChI: InChI=1S/C106H184N28O30/c1-19-55(12)78(125-88(147)67(48-51(4)5)120-90(149)70-33-26-44-131(70)101(160)69(50-135)122-85(144)62(108)37-39-74(139)140)95(154)115-58(15)84(143)116-63(30-22-23-41-107)87(146)123-76(53(8)9)94(153)121-68(49-52(6)7)89(148)128-82(60(17)137)99(158)129-81(59(16)136)98(157)118-65(38-40-75(141)142)100(159)134-47-29-36-73(134)102(161)132-45-27-34-71(132)92(151)126-79(56(13)20-2)96(155)127-80(57(14)21-3)97(156)130-83(61(18)138)103(162)133-46-28-35-72(133)91(150)124-77(54(10)11)93(152)117-64(31-24-42-113-105(109)110)86(145)119-66(104(163)164)32-25-43-114-106(111)112/h51-73,76-83,135-138H,19-50,107-108H2,1-18H3,(H,115,154)(H,116,143)(H,117,152)(H,118,157)(H,119,145)(H,120,149)(H,121,153)(H,122,144)(H,123,146)(H,124,150)(H,125,147)(H,126,151)(H,127,155)(H,128,148)(H,129,158)(H,130,156)(H,139,140)(H,141,142)(H,163,164)(H4,109,110,113)(H4,111,112,114)/t55-,56-,57-,58-,59+,60+,61+,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,76-,77-,78-,79-,80-,81-,82-,83-/m0/s1
• InChIKey: BLFWHYXWBKKRHI-JYBILGDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-methylpentanamido]propanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]-5-[(2S)-2-[(2S)-2-{[(1S,2S)-1-{[(1S,2S)-1-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}butyl]carbamoyl}-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-5-oxopentanoic acid
• IUPAC Traditional name: (4S)-4-[(2S,3R)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S,3S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-4-carboxybutanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-methylpentanamido]propanamido]hexanamido]-3-methylbutanamido]-4-methylpentanamido]-3-hydroxybutanamido]-3-hydroxybutanamido]-5-[(2S)-2-[(2S)-2-{[(1S,2S)-1-{[(1S,2S)-1-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(1S)-4-carbamimidamido-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}butyl]carbamoyl}-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-hydroxy-1-oxobutan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-methylbutyl]carbamoyl}pyrrolidine-1-carbonyl]pyrrolidin-1-yl]-5-oxopentanoic acid
• Synonyms: PLAP; Phospholipase A2 activating peptide; Glu-Ser-Pro-Leu-Ile-Ala-Lys-Val-Leu-Thr-Thr-Glu-Pro-Pro-Ile-Ile-Thr-Pro-Val-Arg-Arg

Database IDs

• CAS Number: 137314-60-4
• MDL Number: MFCD00171646
• PubChem SID: 162225668
• PubChem CID: 71308437

CALCULATED PROPERTIES

• Acid pKa: 3.0185943
• H Acceptors: 38
• H Donor: 31
• LogD (pH = 5.5): -15.596085
• LogD (pH = 7.4): -13.902905
• Log P: -13.16711
• Molar Refractivity: 608.5057 cm^3
• Polarizability: 231.10402 Å^3
• Polar Surface Area: 915.5 Å^2
• Rotatable Bonds: 71
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - G1153

Biochem/physiol Actions
Induced in smooth muscle and endothelial cells treated with leukotriene D4; activates phospholipase A2.