2-[2-(6-amino-2-{6-amino-2-[2-(2-{2-[6-amino-2-(2-{2-[2-(2-{6-amino-2-[2-(2-{2-[2-(2-{[1-(2-{2-[2-(6-amino-2-{4-carboxy-2-[2-(2-{2-[2-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanamido}hexanamido)-3-hydroxypropanamido]-4-carbamoylbutanamido}-3-hydroxybutanoyl)pyrrolidin-2-yl]formamido}-4-methylpentanamido)-3-methylbutanamido]-3-hydroxybutanamido}-4-methylpentanamido)-3-phenylpropanamido]hexanamido}-3-carbamoylpropanamido)propanamido]-3-methylpentanamido}-3-methylpentanamido)hexanamido]-3-carbamoylpropanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]hexanamido}hexanamido)acetamido]pentanedioic acid

• ChemBase ID: 132253
• Molecular Formular: C160H253N39O47S
• Molecular Mass: 3507.01892
• Monoisotopic Mass: 3504.83267743
• 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)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NCC(=O)NC(CCC(=O)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)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)O)CCC(=O)O)CCCCN)CCCCN)Cc1ccc(cc1)O)C)CC(=O)N)CCCCN)C(CC)C)C(CC)C)C)CC(=O)N)NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(C(C)C)NC(=O)C(NC(=O)C1CCCN1C(=O)C(C(O)C)NC(=O)C(NC(=O)C(NC(=O)C(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)CCCCN)CO)CCC(=O)N)CC(C)C)CC(C)C)Cc1ccccc1
• InChI: InChI=1S/C160H253N39O47S/c1-18-85(9)128(155(240)184-103(45-30-35-66-165)139(224)188-114(75-120(167)209)144(229)172-87(11)133(218)185-112(74-96-49-53-98(207)54-50-96)148(233)179-100(42-27-32-63-162)137(222)177-99(41-26-31-62-161)135(220)171-79-124(213)175-107(160(245)246)57-60-126(216)217)195-156(241)129(86(10)19-2)194-134(219)88(12)173-145(230)115(76-121(168)210)187-138(223)101(43-28-33-64-163)180-149(234)113(72-94-39-24-21-25-40-94)186-146(231)108(69-82(3)4)190-157(242)131(90(14)203)197-154(239)127(84(7)8)193-150(235)109(70-83(5)6)189-153(238)118-46-36-67-199(118)159(244)132(91(15)204)198-142(227)104(55-58-119(166)208)181-151(236)116(80-200)191-140(225)102(44-29-34-65-164)178-141(226)105(56-59-125(214)215)182-152(237)117(81-201)192-158(243)130(89(13)202)196-143(228)106(61-68-247-17)183-147(232)111(71-93-37-22-20-23-38-93)176-123(212)78-169-122(211)77-170-136(221)110(174-92(16)205)73-95-47-51-97(206)52-48-95/h20-25,37-40,47-54,82-91,99-118,127-132,200-204,206-207H,18-19,26-36,41-46,55-81,161-165H2,1-17H3,(H2,166,208)(H2,167,209)(H2,168,210)(H,169,211)(H,170,221)(H,171,220)(H,172,229)(H,173,230)(H,174,205)(H,175,213)(H,176,212)(H,177,222)(H,178,226)(H,179,233)(H,180,234)(H,181,236)(H,182,237)(H,183,232)(H,184,240)(H,185,218)(H,186,231)(H,187,223)(H,188,224)(H,189,238)(H,190,242)(H,191,225)(H,192,243)(H,193,235)(H,194,219)(H,195,241)(H,196,228)(H,197,239)(H,198,227)(H,214,215)(H,216,217)(H,245,246)
• InChIKey: FOABCKXRBHNWGH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(6-amino-2-{6-amino-2-[2-(2-{2-[6-amino-2-(2-{2-[2-(2-{6-amino-2-[2-(2-{2-[2-(2-{[1-(2-{2-[2-(6-amino-2-{4-carboxy-2-[2-(2-{2-[2-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanamido}hexanamido)-3-hydroxypropanamido]-4-carbamoylbutanamido}-3-hydroxybutanoyl)pyrrolidin-2-yl]formamido}-4-methylpentanamido)-3-methylbutanamido]-3-hydroxybutanamido}-4-methylpentanamido)-3-phenylpropanamido]hexanamido}-3-carbamoylpropanamido)propanamido]-3-methylpentanamido}-3-methylpentanamido)hexanamido]-3-carbamoylpropanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]hexanamido}hexanamido)acetamido]pentanedioic acid
• IUPAC Traditional name: 2-[2-(6-amino-2-{6-amino-2-[2-(2-{2-[6-amino-2-(2-{2-[2-(2-{6-amino-2-[2-(2-{2-[2-(2-{[1-(2-{2-[2-(6-amino-2-{4-carboxy-2-[2-(2-{2-[2-(2-{2-[2-acetamido-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido}-3-hydroxybutanamido)-3-hydroxypropanamido]butanamido}hexanamido)-3-hydroxypropanamido]-4-carbamoylbutanamido}-3-hydroxybutanoyl)pyrrolidin-2-yl]formamido}-4-methylpentanamido)-3-methylbutanamido]-3-hydroxybutanamido}-4-methylpentanamido)-3-phenylpropanamido]hexanamido}-3-carbamoylpropanamido)propanamido]-3-methylpentanamido}-3-methylpentanamido)hexanamido]-3-carbamoylpropanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]hexanamido}hexanamido)acetamido]pentanedioic acid
• Synonyms: N-Acetyl-β-endorphin Human

Database IDs

• CAS Number: 80102-04-1
• MDL Number: MFCD00076386
• PubChem SID: 24890577; 162226530
• PubChem CID: 16133151

CALCULATED PROPERTIES

• Acid pKa: 2.8351543
• H Acceptors: 52
• H Donor: 48
• LogD (pH = 5.5): -27.785648
• LogD (pH = 7.4): -26.245783
• Log P: -22.203226
• Molar Refractivity: 883.5775 cm^3
• Polarizability: 347.6036 Å^3
• Polar Surface Area: 1406.19 Å^2
• Rotatable Bonds: 119
• 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: ≥95% (HPLC)

DETAILS

Sigma Aldrich - A1660

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-Lys-Lys-Gly-Glu
Other Notes
Predominant form of β-endorphin stored in and released from the intermediate lobe of the pituitary under conditions of foot shock or swim stress.