(4S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S)-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-[(2S)-2-[(2S)-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: 103778
• Molecular Formular: C139H217N33O40S
• Molecular Mass: 3022.47238
• Monoisotopic Mass: 3020.56812991
• SMILES: NCCCC[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@@H](N)Cc1ccc(O)cc1)Cc1ccccc1)C(C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C(C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)CC)C(=O)N[C@@H](C(C)CC)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O
• Canonical SMILES: NCCCC[C@@H](C(=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)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)N[C@H](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@@H](NC(=O)[C@@H](NC(=O)[C@H](C(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
• InChI: InChI=1S/C139H217N33O40S/c1-17-73(9)110(134(206)157-89(38-27-30-55-142)119(191)160-97(64-104(145)181)124(196)149-75(11)115(187)163-99(139(211)212)63-83-42-46-85(179)47-43-83)168-135(207)111(74(10)18-2)167-116(188)76(12)150-125(197)98(65-105(146)182)159-118(190)87(36-25-28-53-140)153-128(200)96(62-81-34-23-20-24-35-81)158-126(198)93(58-70(3)4)162-136(208)113(78(14)176)170-133(205)109(72(7)8)166-129(201)94(59-71(5)6)161-132(204)102-39-31-56-172(102)138(210)114(79(15)177)171-122(194)90(48-50-103(144)180)154-130(202)100(68-173)164-120(192)88(37-26-29-54-141)152-121(193)91(49-51-108(185)186)155-131(203)101(69-174)165-137(209)112(77(13)175)169-123(195)92(52-57-213-16)156-127(199)95(61-80-32-21-19-22-33-80)151-107(184)67-147-106(183)66-148-117(189)86(143)60-82-40-44-84(178)45-41-82/h19-24,32-35,40-47,70-79,86-102,109-114,173-179H,17-18,25-31,36-39,48-69,140-143H2,1-16H3,(H2,144,180)(H2,145,181)(H2,146,182)(H,147,183)(H,148,189)(H,149,196)(H,150,197)(H,151,184)(H,152,193)(H,153,200)(H,154,202)(H,155,203)(H,156,199)(H,157,206)(H,158,198)(H,159,190)(H,160,191)(H,161,204)(H,162,208)(H,163,187)(H,164,192)(H,165,209)(H,166,201)(H,167,188)(H,168,207)(H,169,195)(H,170,205)(H,171,194)(H,185,186)(H,211,212)/t73?,74?,75-,76-,77?,78?,79?,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,101-,102-,109-,110-,111-,112-,113-,114-/m0/s1
• InChIKey: CMLHEPBOBGYCBC-DJJSNWIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S)-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-[(2S)-2-[(2S)-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)-1-[(2S)-2-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-5-amino-1-{[(1S)-2-carbamoyl-1-{[(1S)-1-{[(1S)-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-[(2S)-2-[(2S)-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: 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; β-ENDORPHIN, Fragment 1-27

Database IDs

• CAS Number: 76622-84-9
• PubChem SID: 162103107
• PubChem CID: 71299810

CALCULATED PROPERTIES

• Acid pKa: 3.084686
• H Acceptors: 44
• H Donor: 41
• LogD (pH = 5.5): -21.16557
• LogD (pH = 7.4): -18.73683
• Log P: -17.039993
• Molar Refractivity: 764.0232 cm^3
• Polarizability: 300.62692 Å^3
• Polar Surface Area: 1197.37 Å^2
• Rotatable Bonds: 99
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 02152809

Source/Species: Human