(4S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-[({[(1S)-3-carbamoyl-1-carboxypropyl]carbamoyl}methyl)carbamoyl]pentyl]carbamoyl}pentyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-carbamoylethyl]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-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-3-hydroxybutanamido]-3-hydroxypropanamido]butanoic acid

• ChemBase ID: 134005
• Molecular Formular: C157H254N42O44S
• Molecular Mass: 3466.01666
• Monoisotopic Mass: 3463.86498062
• SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCC(=O)N)C(=O)O)NC(=O)[C@H](C)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)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)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)O)CCC(=O)N)CCCCN)CCCCN)Cc1nc[nH]c1)C(C)C)CC(=O)N)CCCCN)[C@H](CC)C)[C@H](CC)C)C)CC(=O)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N)CCSC)CO)CCC(=O)O)CCCCN)CO)CCC(=O)N)CC(C)C)CC(C)C)Cc1ccccc1
• InChI: InChI=1S/C157H254N42O44S/c1-18-84(11)125(152(237)183-100(45-30-35-62-162)135(220)186-111(72-118(167)209)146(231)192-123(82(7)8)150(235)189-109(70-93-73-168-79-172-93)144(229)179-97(42-27-32-59-159)133(218)176-96(41-26-31-58-158)132(217)171-76-121(212)174-104(157(242)243)52-55-116(165)207)195-153(238)126(85(12)19-2)194-130(215)86(13)173-140(225)110(71-117(166)208)185-134(219)98(43-28-33-60-160)178-143(228)108(69-91-39-24-21-25-40-91)184-141(226)105(65-80(3)4)188-154(239)128(88(15)203)197-151(236)124(83(9)10)193-145(230)106(66-81(5)6)187-149(234)114-46-36-63-199(114)156(241)129(89(16)204)198-138(223)101(51-54-115(164)206)180-147(232)112(77-200)190-136(221)99(44-29-34-61-161)177-137(222)102(53-56-122(213)214)181-148(233)113(78-201)191-155(240)127(87(14)202)196-139(224)103(57-64-244-17)182-142(227)107(68-90-37-22-20-23-38-90)175-120(211)75-169-119(210)74-170-131(216)95(163)67-92-47-49-94(205)50-48-92/h20-25,37-40,47-50,73,79-89,95-114,123-129,200-205H,18-19,26-36,41-46,51-72,74-78,158-163H2,1-17H3,(H2,164,206)(H2,165,207)(H2,166,208)(H2,167,209)(H,168,172)(H,169,210)(H,170,216)(H,171,217)(H,173,225)(H,174,212)(H,175,211)(H,176,218)(H,177,222)(H,178,228)(H,179,229)(H,180,232)(H,181,233)(H,182,227)(H,183,237)(H,184,226)(H,185,219)(H,186,220)(H,187,234)(H,188,239)(H,189,235)(H,190,221)(H,191,240)(H,192,231)(H,193,230)(H,194,215)(H,195,238)(H,196,224)(H,197,236)(H,198,223)(H,213,214)(H,242,243)/t84-,85-,86-,87+,88+,89+,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,123-,124-,125-,126-,127-,128-,129-/m0/s1
• InChIKey: KSZMZNRVPCEDEO-KFHPFRHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-[({[(1S)-3-carbamoyl-1-carboxypropyl]carbamoyl}methyl)carbamoyl]pentyl]carbamoyl}pentyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-carbamoylethyl]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-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-3-hydroxybutanamido]-3-hydroxypropanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(2S,3R)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S,2R)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S,2S)-1-{[(1S,2S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-5-amino-1-[({[(1S)-3-carbamoyl-1-carboxypropyl]carbamoyl}methyl)carbamoyl]pentyl]carbamoyl}pentyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-2-carbamoylethyl]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-[(2S)-2-[(2S,3R)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-3-hydroxybutanamido]-3-hydroxypropanamido]butanoic acid
• Synonyms: β-Lipotropin 61-91; β-Endorphin rat

Database IDs

• CAS Number: 77367-63-6
• MDL Number: MFCD00133129
• PubChem SID: 162228282
• PubChem CID: 71308750

CALCULATED PROPERTIES

• Acid pKa: 3.0515928
• H Acceptors: 51
• H Donor: 48
• LogD (pH = 5.5): -32.24907
• LogD (pH = 7.4): -28.682459
• Log P: -21.678137
• Molar Refractivity: 875.3476 cm^3
• Polarizability: 344.76987 Å^3
• Polar Surface Area: 1417.35 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

Pharmacology Properties

• Gene Information: rat ... Pomc(24664)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - E1142

Amino Acid Sequence
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-Val-His-Lys-Lys-Gly-Gln
Biochem/physiol Actions
Potent endogenous opioid protein that is derived from propiomelanocortin, a protein found in the brain, anterior pituitary, skin, immune system, and other peripheral sites. It is released in response to painful stimuli and has potent antinociceptive activity that is mediated through its action on μ receptors in brain and by μ and κ receptors in the spinal cord.