(4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-3-carbamoylpropanamido]acetamido}propanamido]-4-carboxybutanamido]-3-carboxypropanamido]-4-carboxybutanamido]-3-hydroxypropanamido]propanamido]-4-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-3-carboxy-1-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamoyl}ethyl]carbamoyl}butanoic acid

• ChemBase ID: 153797
• Molecular Formular: C90H125N19O32
• Molecular Mass: 1985.0636
• Monoisotopic Mass: 1983.87380294
• SMILES: C[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)NC(=O)CNC(=O)[C@H](CC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](C(C)C)N
• Canonical SMILES: OC[C@@H](C(=O)N[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)O)Cc1ccccc1)CCC(=O)O)CC(C)C)Cc1ccccc1)C)CCC(=O)O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H](C(C)C)N)Cc1ccc(cc1)O)CC(=O)N)C)CCC(=O)O)CC(=O)O)CCC(=O)O
• InChI: InChI=1S/C90H125N19O32/c1-44(2)36-57(82(132)99-55(28-32-70(118)119)80(130)106-62(90(140)141)39-50-18-12-9-13-19-50)102-85(135)64-20-14-34-108(64)88(138)60(37-49-16-10-8-11-17-49)104-76(126)48(7)95-78(128)53(26-30-68(114)115)97-75(125)47(6)96-84(134)63(43-110)107-81(131)56(29-33-71(120)121)100-83(133)59(41-72(122)123)101-79(129)54(27-31-69(116)117)98-74(124)46(5)94-67(113)42-93-77(127)58(40-66(91)112)103-86(136)65-21-15-35-109(65)89(139)61(105-87(137)73(92)45(3)4)38-51-22-24-52(111)25-23-51/h8-13,16-19,22-25,44-48,53-65,73,110-111H,14-15,20-21,26-43,92H2,1-7H3,(H2,91,112)(H,93,127)(H,94,113)(H,95,128)(H,96,134)(H,97,125)(H,98,124)(H,99,132)(H,100,133)(H,101,129)(H,102,135)(H,103,136)(H,104,126)(H,105,137)(H,106,130)(H,107,131)(H,114,115)(H,116,117)(H,118,119)(H,120,121)(H,122,123)(H,140,141)/t46-,47-,48-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,73-/m0/s1
• InChIKey: VNYTZTMGIJDKGF-SYGRCPSDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-3-carbamoylpropanamido]acetamido}propanamido]-4-carboxybutanamido]-3-carboxypropanamido]-4-carboxybutanamido]-3-hydroxypropanamido]propanamido]-4-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-3-carboxy-1-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamoyl}ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: (4S)-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-3-methylbutanamido]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]formamido}-3-carbamoylpropanamido]acetamido}propanamido]-4-carboxybutanamido]-3-carboxypropanamido]-4-carboxybutanamido]-3-hydroxypropanamido]propanamido]-4-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1S)-1-{[(1S)-3-carboxy-1-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}propyl]carbamoyl}-3-methylbutyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamoyl}ethyl]carbamoyl}butanoic acid
• Synonyms: β-Cell-Tropin; ACTH (22-39); Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Glu-Ala-Phe-Pro-Leu-Glu-Phe; Adrenocorticoptropic Hormone Fragment 22 - 39

Database IDs

• MDL Number: MFCD00076176
• PubChem SID: 162247936
• PubChem CID: 71311732

CALCULATED PROPERTIES

• Acid pKa: 2.7343433
• H Acceptors: 33
• H Donor: 25
• LogD (pH = 5.5): -18.568851
• LogD (pH = 7.4): -26.3194
• Log P: -10.104871
• Molar Refractivity: 482.5428 cm^3
• Polarizability: 189.23822 Å^3
• Polar Surface Area: 810.49 Å^2
• Rotatable Bonds: 59
• 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: human ... POMC(5443)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C90H125N19O32

DETAILS

Sigma Aldrich - A2227

Amino Acid Sequence
Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Glu-Ala-Phe-Pro-Leu-Glu-Phe