(2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-(2-aminoacetamido)-3-(1H-indol-3-yl)propanamido]-3-hydroxybutanamido]-4-methylpentanamido]-N-[(1R,2S)-2-hydroxy-1-{[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1S)-1-{[(1S)-1-({2-[(2S)-2-{[(1S)-1-{[(2S)-1-hydroxypropan-2-yl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}ethyl]carbamoyl}propyl]butanediamide

• ChemBase ID: 131978
• Molecular Formular: C84H117N21O18
• Molecular Mass: 1708.95768
• Monoisotopic Mass: 1707.88854601
• SMILES: C[C@@H](CO)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](C)NC(=O)[C@@H]([C@H](C)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)CN
• Canonical SMILES: OC[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H]([C@@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@H](O)C)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)CN)CC(C)C)CC(=O)N)C)CC(C)C)CC(C)C)Cc1nc[nH]c1)C
• InChI: InChI=1S/C84H117N21O18/c1-42(2)26-59(74(113)91-39-70(111)105-25-17-24-67(105)82(121)101-65(32-52-38-87-41-92-52)75(114)93-45(7)40-106)97-76(115)60(27-43(3)4)98-79(118)64(31-51-37-90-58-23-16-13-20-55(51)58)99-78(117)63(30-50-36-89-57-22-15-12-19-54(50)57)96-73(112)46(8)94-83(122)71(47(9)107)103-81(120)66(33-68(86)109)100-77(116)61(28-44(5)6)102-84(123)72(48(10)108)104-80(119)62(95-69(110)34-85)29-49-35-88-56-21-14-11-18-53(49)56/h11-16,18-23,35-38,41-48,59-67,71-72,88-90,106-108H,17,24-34,39-40,85H2,1-10H3,(H2,86,109)(H,87,92)(H,91,113)(H,93,114)(H,94,122)(H,95,110)(H,96,112)(H,97,115)(H,98,118)(H,99,117)(H,100,116)(H,101,121)(H,102,123)(H,103,120)(H,104,119)/t45-,46-,47-,48+,59-,60-,61-,62-,63+,64+,65-,66-,67-,71+,72-/m0/s1
• InChIKey: YVZGSAYDOLVILH-XFVAFISTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-(2-aminoacetamido)-3-(1H-indol-3-yl)propanamido]-3-hydroxybutanamido]-4-methylpentanamido]-N-[(1R,2S)-2-hydroxy-1-{[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1S)-1-{[(1S)-1-({2-[(2S)-2-{[(1S)-1-{[(2S)-1-hydroxypropan-2-yl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}ethyl]carbamoyl}propyl]butanediamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S,3R)-2-[(2S)-2-(2-aminoacetamido)-3-(1H-indol-3-yl)propanamido]-3-hydroxybutanamido]-4-methylpentanamido]-N-[(1R,2S)-2-hydroxy-1-{[(1S)-1-{[(1R)-1-{[(1R)-1-{[(1S)-1-{[(1S)-1-({2-[(2S)-2-{[(1S)-1-{[(2S)-1-hydroxypropan-2-yl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}pyrrolidin-1-yl]-2-oxoethyl}carbamoyl)-3-methylbutyl]carbamoyl}-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}ethyl]carbamoyl}propyl]butanediamide
• Synonyms: [D-Thr6, D-Trp8,9, 15-ol]-Galanin fragment 1-15

Database IDs

• CAS Number: 150940-97-9
• MDL Number: MFCD01861110
• PubChem SID: 162226255
• PubChem CID: 71308503

CALCULATED PROPERTIES

• Acid pKa: 11.346012
• H Acceptors: 20
• H Donor: 22
• LogD (pH = 5.5): -6.4322743
• LogD (pH = 7.4): -4.0120077
• Log P: -3.3892639
• Molar Refractivity: 446.4107 cm^3
• Polarizability: 177.45372 Å^3
• Polar Surface Area: 604.46 Å^2
• Rotatable Bonds: 46
• 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 ... GAL(51083)

DETAILS

Sigma Aldrich - G3535

Amino Acid Sequence
Gly-Trp-Thr-Leu-Asn-D-Thr-Ala-D-Trp-D-Trp-Leu-Leu-Gly-Pro-His-Ala-ol
Biochem/physiol Actions
A potent galanin antagonist at sub-micromolar concentrations.