(2S)-2-[(2S)-2-(2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-aminoacetamido)-3-phenylpropanamido]-3-phenylpropanamido]propanamido]-4-methylpentanamido]-3-methylpentanoyl]pyrrolidin-2-yl]formamido}hexanamido]-3-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-phenylpropanamido]hexanamido]-3-hydroxybutanamido]-4-methylpentanamido]-4-methylpentanamido]-3-hydroxypropanamido]propanamido]-3-methylbutanamido]acetamido}-3-hydroxypropanamido]propanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]acetamido}acetamido)-4-carbamoylbutanamido]pentanedioic acid

• ChemBase ID: 132475
• Molecular Formular: C154H248N36O45
• Molecular Mass: 3323.83112
• Monoisotopic Mass: 3321.82243002
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)NCC(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)CN
• 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)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[C@H](C(=O)NCC(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCC(=O)O)CCC(=O)N)CO)CO)CO)CC(C)C)C)CO)C(C)C)C)CO)CC(C)C)CC(C)C)[C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](CC)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CN)Cc1ccccc1)C)CC(C)C)CCCCN)CO)CO)CC(C)C)Cc1ccccc1
• InChI: InChI=1S/C154H248N36O45/c1-23-84(16)122(186-150(230)123(85(17)24-2)185-131(211)95(48-36-38-56-156)169-146(226)114-50-40-58-190(114)153(233)124(86(18)25-3)187-140(220)102(63-82(12)13)172-126(206)87(19)162-133(213)104(65-92-43-31-27-32-44-92)174-138(218)103(166-116(200)67-157)64-91-41-29-26-30-42-91)149(229)182-111(76-196)145(225)183-112(77-197)152(232)189-57-39-49-113(189)147(227)176-100(61-80(8)9)134(214)175-105(66-93-45-33-28-34-46-93)139(219)168-94(47-35-37-55-155)132(212)188-125(90(22)198)151(231)177-101(62-81(10)11)135(215)173-99(60-79(6)7)137(217)179-108(73-193)142(222)164-89(21)128(208)184-121(83(14)15)148(228)161-70-119(203)167-107(72-192)141(221)163-88(20)127(207)171-98(59-78(4)5)136(216)180-109(74-194)144(224)181-110(75-195)143(223)178-106(71-191)129(209)160-68-117(201)159-69-118(202)165-96(51-53-115(158)199)130(210)170-97(154(234)235)52-54-120(204)205/h26-34,41-46,78-90,94-114,121-125,191-198H,23-25,35-40,47-77,155-157H2,1-22H3,(H2,158,199)(H,159,201)(H,160,209)(H,161,228)(H,162,213)(H,163,221)(H,164,222)(H,165,202)(H,166,200)(H,167,203)(H,168,219)(H,169,226)(H,170,210)(H,171,207)(H,172,206)(H,173,215)(H,174,218)(H,175,214)(H,176,227)(H,177,231)(H,178,223)(H,179,217)(H,180,216)(H,181,224)(H,182,229)(H,183,225)(H,184,208)(H,185,211)(H,186,230)(H,187,220)(H,188,212)(H,204,205)(H,234,235)/t84-,85-,86-,87-,88-,89-,90+,94-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,121-,122-,123-,124-,125-/m0/s1
• InChIKey: CTVQQQPWNOVEAG-QDOPKCMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-(2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-aminoacetamido)-3-phenylpropanamido]-3-phenylpropanamido]propanamido]-4-methylpentanamido]-3-methylpentanoyl]pyrrolidin-2-yl]formamido}hexanamido]-3-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-phenylpropanamido]hexanamido]-3-hydroxybutanamido]-4-methylpentanamido]-4-methylpentanamido]-3-hydroxypropanamido]propanamido]-3-methylbutanamido]acetamido}-3-hydroxypropanamido]propanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]acetamido}acetamido)-4-carbamoylbutanamido]pentanedioic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-(2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S,3S)-2-[(2S,3S)-2-[(2S)-6-amino-2-{[(2S)-1-[(2S,3S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-aminoacetamido)-3-phenylpropanamido]-3-phenylpropanamido]propanamido]-4-methylpentanamido]-3-methylpentanoyl]pyrrolidin-2-yl]formamido}hexanamido]-3-methylpentanamido]-3-methylpentanamido]-3-hydroxypropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-phenylpropanamido]hexanamido]-3-hydroxybutanamido]-4-methylpentanamido]-4-methylpentanamido]-3-hydroxypropanamido]propanamido]-3-methylbutanamido]acetamido}-3-hydroxypropanamido]propanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]-3-hydroxypropanamido]acetamido}acetamido)-4-carbamoylbutanamido]pentanedioic acid
• Synonyms: Gly-Phe-Phe-Ala-Leu-Ile-Pro-Lys-Ile-Ile-Ser-Ser-Pro-Leu-Phe-Lys-Thr-Leu-Leu-Ser-Ala-Val-Gly-Ser-Ala-Leu-Ser-Ser-Ser-Gly-Gly-Gln-Glu; [Gly31]-Pardaxin P1; Pardaxin

Database IDs

• CAS Number: 134940-98-0
• PubChem SID: 162226752
• PubChem CID: 16143997

CALCULATED PROPERTIES

• Acid pKa: 3.0219588
• H Acceptors: 48
• H Donor: 44
• LogD (pH = 5.5): -19.87921
• LogD (pH = 7.4): -18.184832
• Log P: -17.690868
• Molar Refractivity: 838.2229 cm^3
• Polarizability: 330.0508 Å^3
• Polar Surface Area: 1271.21 Å^2
• Rotatable Bonds: 108
• 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

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - P0435

Biochem/physiol Actions
Induces neurotransmitter release
Other Notes
Originally isolated from Pardachirus marmoratus (Moses sole)