(4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-[({[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}methyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido]-4-(methylsulfanyl)butanamido]butanoic acid

• ChemBase ID: 155480
• Molecular Formular: C95H145N29O23S
• Molecular Mass: 2093.4133
• Monoisotopic Mass: 2092.07888305
• SMILES: CC(C)[C@@H](C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)NC(=O)CNC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CO)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)CCCCN)CCCCN)C(C)C)NC(=O)CNC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CO)N)Cc1ccc(cc1)O)CO)CCSC)CCC(=O)O)Cc1nc[nH]c1)Cc1ccccc1)CCCNC(=N)N
• InChI: InChI=1S/C95H145N29O23S/c1-53(2)78(91(144)109-49-75(128)111-62(22-9-12-35-96)81(134)113-63(23-10-13-36-97)82(135)117-68(93(146)147)26-16-39-106-95(102)103)123-90(143)74-27-17-40-124(74)92(145)67(24-11-14-37-98)112-76(129)48-108-80(133)71(44-56-46-107-61-21-8-7-20-59(56)61)120-83(136)64(25-15-38-105-94(100)101)114-86(139)70(42-54-18-5-4-6-19-54)119-88(141)72(45-57-47-104-52-110-57)121-84(137)65(32-33-77(130)131)115-85(138)66(34-41-148-3)116-89(142)73(51-126)122-87(140)69(118-79(132)60(99)50-125)43-55-28-30-58(127)31-29-55/h4-8,18-21,28-31,46-47,52-53,60,62-74,78,107,125-127H,9-17,22-27,32-45,48-51,96-99H2,1-3H3,(H,104,110)(H,108,133)(H,109,144)(H,111,128)(H,112,129)(H,113,134)(H,114,139)(H,115,138)(H,116,142)(H,117,135)(H,118,132)(H,119,141)(H,120,136)(H,121,137)(H,122,140)(H,123,143)(H,130,131)(H,146,147)(H4,100,101,105)(H4,102,103,106)/t60-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,78-/m0/s1
• InChIKey: MXNMAFWEFLFAJN-QBQLSIIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-[({[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}methyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido]-4-(methylsulfanyl)butanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(2S)-6-amino-1-[(2S)-2-{[(1S)-1-[({[(1S)-5-amino-1-{[(1S)-5-amino-1-{[(1S)-4-carbamimidamido-1-carboxybutyl]carbamoyl}pentyl]carbamoyl}pentyl]carbamoyl}methyl)carbamoyl]-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}methyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]carbamoyl}-4-carbamimidamidobutyl]carbamoyl}-2-phenylethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]-3-hydroxypropanamido]-4-(methylsulfanyl)butanamido]butanoic acid
• Synonyms: Adrenocorticotropic Hormone Fragment 1-17 human, rat

Database IDs

• CAS Number: 7266-47-9
• MDL Number: MFCD00133033
• PubChem SID: 162249618
• PubChem CID: 71312141

CALCULATED PROPERTIES

• Acid pKa: 3.1839895
• H Acceptors: 34
• H Donor: 32
• LogD (pH = 5.5): -23.198435
• LogD (pH = 7.4): -20.299294
• Log P: -12.379332
• Molar Refractivity: 558.6277 cm^3
• Polarizability: 210.83258 Å^3
• Polar Surface Area: 864.45 Å^2
• Rotatable Bonds: 69
• 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: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C95H145N29O23S

DETAILS

Sigma Aldrich - A2407

Amino Acid Sequence
Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-Gly-Lys-Lys-Arg
Biochem/physiol Actions
ACTH fragment with moderate adrenocorticotropic and melanocyte-stimulating activities.