3-({5-amino-1-[(1-{[({1-[(1-carbamoyl-2-hydroxypropyl)carbamoyl]-3-methylbutyl}carbamoyl)methyl]carbamoyl}-2-(1H-imidazol-5-yl)ethyl)carbamoyl]pentyl}carbamoyl)-3-{2-[2-(2-{2-[2-(2-{2-[2-(2-{2-[(1-{2-[2-(2-{2-[2-(2-{2-[2-(2-{2-[2-(2-aminoacetamido)-3-(1H-indol-3-yl)propanamido]-3-hydroxybutanamido}-4-methylpentanamido)-3-carbamoylpropanamido]-3-hydroxypropanamido}propanamido)acetamido]-3-(4-hydroxyphenyl)propanamido}-4-methylpentanamido)-4-methylpentanamido]acetyl}pyrrolidin-2-yl)formamido]-3-(1H-imidazol-5-yl)propanamido}propanamido)-3-methylpentanamido]-3-carboxypropanamido}-3-carbamoylpropanamido)-3-(1H-imidazol-5-yl)propanamido]-5-carbamimidamidopentanamido}-3-hydroxypropanamido)-3-phenylpropanamido]-3-hydroxypropanamido}propanoic acid

• ChemBase ID: 103796
• Molecular Formular: C141H211N43O41
• Molecular Mass: 3164.44754
• Monoisotopic Mass: 3162.57476339
• SMILES: NCCCCC(NC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(Cc1ccccc1)NC(=O)C(CO)NC(=O)C(CCCNC(=N)N)NC(=O)C(Cc1[nH]cnc1)NC(=O)C(CC(=O)N)NC(=O)C(CC(=O)O)NC(=O)C(NC(=O)C(C)NC(=O)C(Cc1[nH]cnc1)NC(=O)C1CCCN1C(=O)CNC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)CNC(=O)C(C)NC(=O)C(CO)NC(=O)C(CC(=O)N)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(NC(=O)CN)Cc1c[nH]c2ccccc12)C(C)O)Cc1ccc(O)cc1)C(C)CC)C(=O)NC(Cc1[nH]cnc1)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(C(C)O)C(=O)N
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N)C(O)C)CC(C)C)Cc1[nH]cnc1)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(CC)C)NC(=O)C(NC(=O)C(NC(=O)C1CCCN1C(=O)CNC(=O)C(NC(=O)C(NC(=O)C(Cc1ccc(cc1)O)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(C(O)C)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)CN)CC(C)C)CC(=O)N)CO)C)CC(C)C)CC(C)C)Cc1[nH]cnc1)C)CC(=O)O)CC(=O)N)Cc1[nH]cnc1)CCCNC(=N)N)CO)Cc1ccccc1)CO)CC(=O)O
• InChI: InChI=1S/C141H211N43O41/c1-15-71(10)113(139(224)177-100(52-112(199)200)132(217)173-97(49-105(144)191)129(214)171-96(48-81-57-151-66-159-81)128(213)166-86(30-23-37-152-141(147)148)122(207)178-102(62-186)136(221)169-92(43-76-25-17-16-18-26-76)127(212)180-103(63-187)137(222)174-99(51-111(197)198)131(216)165-85(29-21-22-36-142)121(206)170-94(46-79-55-149-64-157-79)120(205)155-59-109(195)163-88(40-68(4)5)133(218)182-114(74(13)188)116(146)201)181-118(203)73(12)161-123(208)95(47-80-56-150-65-158-80)175-138(223)104-31-24-38-184(104)110(196)60-156-119(204)87(39-67(2)3)167-124(209)89(41-69(6)7)168-126(211)91(44-77-32-34-82(190)35-33-77)164-108(194)58-154-117(202)72(11)160-135(220)101(61-185)179-130(215)98(50-106(145)192)172-125(210)90(42-70(8)9)176-140(225)115(75(14)189)183-134(219)93(162-107(193)53-143)45-78-54-153-84-28-20-19-27-83(78)84/h16-20,25-28,32-35,54-57,64-75,85-104,113-115,153,185-190H,15,21-24,29-31,36-53,58-63,142-143H2,1-14H3,(H2,144,191)(H2,145,192)(H2,146,201)(H,149,157)(H,150,158)(H,151,159)(H,154,202)(H,155,205)(H,156,204)(H,160,220)(H,161,208)(H,162,193)(H,163,195)(H,164,194)(H,165,216)(H,166,213)(H,167,209)(H,168,211)(H,169,221)(H,170,206)(H,171,214)(H,172,210)(H,173,217)(H,174,222)(H,175,223)(H,176,225)(H,177,224)(H,178,207)(H,179,215)(H,180,212)(H,181,203)(H,182,218)(H,183,219)(H,197,198)(H,199,200)(H4,147,148,152)
• InChIKey: JHQDYHHNJBOXKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-({5-amino-1-[(1-{[({1-[(1-carbamoyl-2-hydroxypropyl)carbamoyl]-3-methylbutyl}carbamoyl)methyl]carbamoyl}-2-(1H-imidazol-5-yl)ethyl)carbamoyl]pentyl}carbamoyl)-3-{2-[2-(2-{2-[2-(2-{2-[2-(2-{2-[(1-{2-[2-(2-{2-[2-(2-{2-[2-(2-{2-[2-(2-aminoacetamido)-3-(1H-indol-3-yl)propanamido]-3-hydroxybutanamido}-4-methylpentanamido)-3-carbamoylpropanamido]-3-hydroxypropanamido}propanamido)acetamido]-3-(4-hydroxyphenyl)propanamido}-4-methylpentanamido)-4-methylpentanamido]acetyl}pyrrolidin-2-yl)formamido]-3-(1H-imidazol-5-yl)propanamido}propanamido)-3-methylpentanamido]-3-carboxypropanamido}-3-carbamoylpropanamido)-3-(1H-imidazol-5-yl)propanamido]-5-carbamimidamidopentanamido}-3-hydroxypropanamido)-3-phenylpropanamido]-3-hydroxypropanamido}propanoic acid
• IUPAC Traditional name: 3-({5-amino-1-[(1-{[({1-[(1-carbamoyl-2-hydroxypropyl)carbamoyl]-3-methylbutyl}carbamoyl)methyl]carbamoyl}-2-(3H-imidazol-4-yl)ethyl)carbamoyl]pentyl}carbamoyl)-3-{2-[2-(2-{2-[2-(2-{2-[2-(2-{2-[(1-{2-[2-(2-{2-[2-(2-{2-[2-(2-{2-[2-(2-aminoacetamido)-3-(1H-indol-3-yl)propanamido]-3-hydroxybutanamido}-4-methylpentanamido)-3-carbamoylpropanamido]-3-hydroxypropanamido}propanamido)acetamido]-3-(4-hydroxyphenyl)propanamido}-4-methylpentanamido)-4-methylpentanamido]acetyl}pyrrolidin-2-yl)formamido]-3-(3H-imidazol-4-yl)propanamido}propanamido)-3-methylpentanamido]-3-carboxypropanamido}-3-carbamoylpropanamido)-3-(3H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido}-3-hydroxypropanamido)-3-phenylpropanamido]-3-hydroxypropanamido}propanoic acid
• Synonyms: Galanin rat; H-Gly-Trp-Thr-Leu-Asn-Ser-Ala-Gly-Tyr-Leu-Leu-Gly-Pro-His-Ala-Ile-Asp-Asn-His-Arg-Ser-Phe-Ser-Asp-Lys-His-Gly-Leu-Thr-NH₂; GALANIN

Database IDs

• CAS Number: 114547-31-8
• MDL Number: MFCD00133354
• PubChem SID: 162103111; 24895336
• PubChem CID: 16133243

CALCULATED PROPERTIES

• Acid pKa: 3.2822642
• H Acceptors: 49
• H Donor: 47
• LogD (pH = 5.5): -26.991581
• LogD (pH = 7.4): -23.901112
• Log P: -23.200315
• Molar Refractivity: 799.3408 cm^3
• Polarizability: 308.92258 Å^3
• Polar Surface Area: 1347.03 Å^2
• Rotatable Bonds: 99
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• Storage Condition: 0°C
• 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 ... Gal(29141)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ≥65%

DETAILS

MP Biomedicals - 02152865

Source: Rat
Purity: 99.0%

Sigma Aldrich - G8272

Amino Acid Sequence
Gly-Trp-Thr-Leu-Asn-Ser-Ala-Gly-Tyr-Leu-Leu-Gly-Pro-His-Ala-Ile-Asp-Asn-His-Arg-Ser-Phe-Ser-Asp-Lys-His-Gly-Leu-Thr-NH2
Biochem/physiol Actions
Co-localized with acetylcholine and inhibits its release; inhibits the release of glutamic acid, decreases excitability of spinal neurons; blocks voltage-activated Ca2+ channels; linked to behavioral and cognitive deficits in Alzheimer′s disease.

REFERENCES

• Vrontakis, M.E., et al., J. Biol. Chem., 262: 16755, (1987)
• Kaplan,L.M. et al., Proc. Natl. Acad. Sci. USA, 1065 (1988)