4-[(5-amino-1-{[1-({1-[(1-{2-[(1-{[1-({1-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{[5-amino-1-({2-carbamoyl-1-[(1-{[1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl)carbamoyl]ethyl}carbamoyl)pentyl]carbamoyl}-2-methylbutyl)carbamoyl]-2-methylbutyl}carbamoyl)ethyl]carbamoyl}-2-carbamoylethyl)carbamoyl]pentyl}carbamoyl)-2-phenylethyl]carbamoyl}-3-methylbutyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-methylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)carbamoyl]-3-carbamoylpropyl}carbamoyl)-2-hydroxyethyl]carbamoyl}pentyl)carbamoyl]-4-[2-(2-{2-[2-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid

• ChemBase ID: 133675
• Molecular Formular: C141H219N33O41S
• Molecular Mass: 3064.50906
• Monoisotopic Mass: 3062.57869459
• SMILES: CCC(C)C(C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CC(=O)N)C(=O)NC(C)C(=O)NC(Cc1ccc(cc1)O)C(=O)O)NC(=O)C(C)NC(=O)C(CC(=O)N)NC(=O)C(CCCCN)NC(=O)C(Cc1ccccc1)NC(=O)C(CC(C)C)NC(=O)C(C(C)O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C1CCCN1C(=O)C(C(C)O)NC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CCCCN)NC(=O)C(CCC(=O)O)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C(CCSC)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)NC(=O)C
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)Cc1ccc(cc1)O)C)CC(=O)N)CCCCN)C(CC)C)C(CC)C)C)CC(=O)N)CCCCN)Cc1ccccc1)CC(C)C)C(O)C)C(C)C)CC(C)C)C(O)C)CCC(=O)N)CO)NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)C(Cc1ccc(cc1)O)NC(=O)C)CCSC)CO)CCC(=O)O
• InChI: InChI=1S/C141H219N33O41S/c1-18-74(9)112(136(209)159-90(39-28-31-56-144)121(194)162-99(65-106(146)184)126(199)150-76(11)117(190)165-101(141(214)215)64-85-43-47-87(182)48-44-85)170-137(210)113(75(10)19-2)169-118(191)77(12)151-127(200)100(66-107(147)185)161-120(193)88(37-26-29-54-142)155-130(203)98(62-83-35-24-21-25-36-83)160-128(201)94(59-71(3)4)164-138(211)115(79(14)178)172-135(208)111(73(7)8)168-131(204)95(60-72(5)6)163-134(207)104-40-32-57-174(104)140(213)116(80(15)179)173-124(197)91(49-51-105(145)183)156-132(205)102(69-175)166-122(195)89(38-27-30-55-143)154-123(196)92(50-52-110(188)189)157-133(206)103(70-176)167-139(212)114(78(13)177)171-125(198)93(53-58-216-17)158-129(202)97(61-82-33-22-20-23-34-82)153-109(187)68-148-108(186)67-149-119(192)96(152-81(16)180)63-84-41-45-86(181)46-42-84/h20-25,33-36,41-48,71-80,88-104,111-116,175-179,181-182H,18-19,26-32,37-40,49-70,142-144H2,1-17H3,(H2,145,183)(H2,146,184)(H2,147,185)(H,148,186)(H,149,192)(H,150,199)(H,151,200)(H,152,180)(H,153,187)(H,154,196)(H,155,203)(H,156,205)(H,157,206)(H,158,202)(H,159,209)(H,160,201)(H,161,193)(H,162,194)(H,163,207)(H,164,211)(H,165,190)(H,166,195)(H,167,212)(H,168,204)(H,169,191)(H,170,210)(H,171,198)(H,172,208)(H,173,197)(H,188,189)(H,214,215)
• InChIKey: KBTYRLSAENUDCP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(5-amino-1-{[1-({1-[(1-{2-[(1-{[1-({1-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{[5-amino-1-({2-carbamoyl-1-[(1-{[1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl)carbamoyl]ethyl}carbamoyl)pentyl]carbamoyl}-2-methylbutyl)carbamoyl]-2-methylbutyl}carbamoyl)ethyl]carbamoyl}-2-carbamoylethyl)carbamoyl]pentyl}carbamoyl)-2-phenylethyl]carbamoyl}-3-methylbutyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-methylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)carbamoyl]-3-carbamoylpropyl}carbamoyl)-2-hydroxyethyl]carbamoyl}pentyl)carbamoyl]-4-[2-(2-{2-[2-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid
• IUPAC Traditional name: 4-[(5-amino-1-{[1-({1-[(1-{2-[(1-{[1-({1-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{[5-amino-1-({2-carbamoyl-1-[(1-{[1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl)carbamoyl]ethyl}carbamoyl)pentyl]carbamoyl}-2-methylbutyl)carbamoyl]-2-methylbutyl}carbamoyl)ethyl]carbamoyl}-2-carbamoylethyl)carbamoyl]pentyl}carbamoyl)-2-phenylethyl]carbamoyl}-3-methylbutyl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-methylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pyrrolidin-1-yl}-3-hydroxy-1-oxobutan-2-yl)carbamoyl]-3-carbamoylpropyl}carbamoyl)-2-hydroxyethyl]carbamoyl}pentyl)carbamoyl]-4-[2-(2-{2-[2-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanoic acid
• Synonyms: N-Acetyl-β-Endorphin Fragment 1-27 Human

Database IDs

• CAS Number: 76622-86-1
• MDL Number: MFCD00076391
• PubChem SID: 162227952
• PubChem CID: 16133237

CALCULATED PROPERTIES

• Acid pKa: 3.0846958
• H Acceptors: 44
• H Donor: 41
• LogD (pH = 5.5): -19.173653
• LogD (pH = 7.4): -18.420185
• Log P: -17.200224
• Molar Refractivity: 773.467 cm^3
• Polarizability: 304.0416 Å^3
• Polar Surface Area: 1200.45 Å^2
• Rotatable Bonds: 100
• 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 - E0762

Amino Acid Sequence
Ac-Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-lys-Asn-Ala-Tyr
Other Notes
Predominant form of β-endorphin in the intermediate lobe of the pituitary under normal conditions