3-[(1-{[1-({1-[(1-{[1-({1-[(5-amino-1-{[1-({1-[(1-{[1-({5-amino-1-[(5-amino-1-{[1-({1-[(1-{[1-({1-[(1-carbamoyl-3-methylbutyl)carbamoyl]-2-methylpropyl}carbamoyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}pentyl)carbamoyl]pentyl}carbamoyl)-2-methylpropyl]carbamoyl}ethyl)carbamoyl]-3-(methylsulfanyl)propyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}pentyl)carbamoyl]-4-carbamimidamidobutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-4-carbamimidamidobutyl)carbamoyl]-2-hydroxyethyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl)carbamoyl]-3-[2-(2-{2-[2-(2-{2-[2-amino-3-(1H-imidazol-5-yl)propanamido]-3-hydroxypropanamido}-3-carboxypropanamido)acetamido]-3-methylpentanamido}-3-phenylpropanamido)-3-hydroxybutanamido]propanoic acid

• ChemBase ID: 106015
• Molecular Formular: C142H224N40O39S
• Molecular Mass: 3147.60756
• Monoisotopic Mass: 3145.64950855
• SMILES: CCC(C)C(NC(=O)CNC(=O)C(CC(=O)O)NC(=O)C(CO)NC(=O)C(N)Cc1c[nH]cn1)C(=O)NC(Cc1ccccc1)C(=O)NC(C(C)O)C(=O)NC(CC(=O)O)C(=O)NC(CO)C(=O)NC(Cc1ccc(O)cc1)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)NC(Cc1ccc(O)cc1)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CCC(=O)N)C(=O)NC(CCSC)C(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(CCCCN)C(=O)NC(CCCCN)C(=O)NC(Cc1ccc(O)cc1)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)N
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)CC(C)C)C(C)C)C)C)CC(C)C)Cc1ccc(cc1)O)CCCCN)CCCCN)C(C)C)C)CCSC)CCC(=O)N)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(O)C)NC(=O)C(NC(=O)C(C(CC)C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(Cc1nc[nH]c1)N)CO)CC(=O)O)Cc1ccccc1)CC(=O)O)CO)Cc1ccc(cc1)O)CO)CCCNC(=N)N)Cc1ccc(cc1)O)CCCNC(=N)N
• InChI: InChI=1S/C142H224N40O39S/c1-16-75(10)113(179-108(191)66-156-120(201)102(63-109(192)193)173-135(216)104(67-183)176-119(200)88(146)62-84-65-153-70-157-84)139(220)174-101(58-80-28-18-17-19-29-80)133(214)182-114(79(14)186)140(221)175-103(64-110(194)195)132(213)178-106(69-185)136(217)172-100(61-83-39-45-87(189)46-40-83)131(212)177-105(68-184)134(215)164-93(34-27-54-155-142(151)152)126(207)170-98(59-81-35-41-85(187)42-36-81)129(210)163-92(33-26-53-154-141(149)150)124(205)161-89(30-20-23-50-143)122(203)165-94(47-48-107(147)190)127(208)166-95(49-55-222-15)121(202)159-78(13)118(199)180-111(73(6)7)137(218)167-91(32-22-25-52-145)123(204)162-90(31-21-24-51-144)125(206)171-99(60-82-37-43-86(188)44-38-82)130(211)169-97(57-72(4)5)128(209)160-76(11)116(197)158-77(12)117(198)181-112(74(8)9)138(219)168-96(115(148)196)56-71(2)3/h17-19,28-29,35-46,65,70-79,88-106,111-114,183-189H,16,20-27,30-34,47-64,66-69,143-146H2,1-15H3,(H2,147,190)(H2,148,196)(H,153,157)(H,156,201)(H,158,197)(H,159,202)(H,160,209)(H,161,205)(H,162,204)(H,163,210)(H,164,215)(H,165,203)(H,166,208)(H,167,218)(H,168,219)(H,169,211)(H,170,207)(H,171,206)(H,172,217)(H,173,216)(H,174,220)(H,175,221)(H,176,200)(H,177,212)(H,178,213)(H,179,191)(H,180,199)(H,181,198)(H,182,214)(H,192,193)(H,194,195)(H4,149,150,154)(H4,151,152,155)
• InChIKey: RZGBUJXSKLDAFE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1-{[1-({1-[(1-{[1-({1-[(5-amino-1-{[1-({1-[(1-{[1-({5-amino-1-[(5-amino-1-{[1-({1-[(1-{[1-({1-[(1-carbamoyl-3-methylbutyl)carbamoyl]-2-methylpropyl}carbamoyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}pentyl)carbamoyl]pentyl}carbamoyl)-2-methylpropyl]carbamoyl}ethyl)carbamoyl]-3-(methylsulfanyl)propyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}pentyl)carbamoyl]-4-carbamimidamidobutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-4-carbamimidamidobutyl)carbamoyl]-2-hydroxyethyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl)carbamoyl]-3-[2-(2-{2-[2-(2-{2-[2-amino-3-(1H-imidazol-5-yl)propanamido]-3-hydroxypropanamido}-3-carboxypropanamido)acetamido]-3-methylpentanamido}-3-phenylpropanamido)-3-hydroxybutanamido]propanoic acid
• IUPAC Traditional name: 3-[(1-{[1-({1-[(1-{[1-({1-[(5-amino-1-{[1-({1-[(1-{[1-({5-amino-1-[(5-amino-1-{[1-({1-[(1-{[1-({1-[(1-carbamoyl-3-methylbutyl)carbamoyl]-2-methylpropyl}carbamoyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}pentyl)carbamoyl]pentyl}carbamoyl)-2-methylpropyl]carbamoyl}ethyl)carbamoyl]-3-(methylsulfanyl)propyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}pentyl)carbamoyl]-4-carbamimidamidobutyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-4-carbamimidamidobutyl)carbamoyl]-2-hydroxyethyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl)carbamoyl]-3-[2-(2-{2-[2-(2-{2-[2-amino-3-(3H-imidazol-4-yl)propanamido]-3-hydroxypropanamido}-3-carboxypropanamido)acetamido]-3-methylpentanamido}-3-phenylpropanamido)-3-hydroxybutanamido]propanoic acid
• Synonyms: PACAP-27; ADENYLATE CYCLASE ACTIVATING PEPTIDE-27; Pituitary adenylate cyclase activating polypeptide-27 ovine

Database IDs

• CAS Number: 127317-03-7
• MDL Number: MFCD00167418
• PubChem SID: 24891501; 162086869
• PubChem CID: 44134520

CALCULATED PROPERTIES

• Acid pKa: 3.1479423
• H Acceptors: 50
• H Donor: 48
• LogD (pH = 5.5): -27.633898
• LogD (pH = 7.4): -24.69573
• Log P: -16.698112
• Molar Refractivity: 819.6273 cm^3
• Polarizability: 312.5914 Å^3
• Polar Surface Area: 1315.55 Å^2
• Rotatable Bonds: 105
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white solid

Safety Information

• Storage Condition: 2-8°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: human ... ADCY1(107)mouse ... ADCY1(432530)rat ... ADCY1(305509)sheep ... PACAP(443337)

Product Information

• Purity: ≥97%; ≥97% (HPLC)
• Compostion: Peptide content, ~70%
• Empirical Formula (Hill Notation): C142H224N40O39S

DETAILS

MP Biomedicals - 02195879

His-Ser-Asp-Gly-Ile-Phe-Thr-Asp-Ser-Tyr-Ser-Arg-Tyr-Arg-Lys-Gln-Met-Ala-Val-Lys-Lys-Tyr-Leu-Ala-Ala-Val-Leu-NH₂
Purity: >97%

Sigma Aldrich - A9808

Amino Acid Sequence
His-Ser-Asp-Gly-Ile-Phe-Thr-Asp-Ser-Tyr-Ser-Arg-Tyr-Arg-Lys-Gln-Met-Ala-Val-Lys-Lys-Tyr-Leu-Ala-Ala-Val-Leu-NH2
Biochem/physiol Actions
Neuropeptide that stimulates both adenylate cyclase in cultured pituitary cells and insulin release from pancreatic islet β-cells. Increases cAMP levels; increases tyrosine hydroxylase expression in chromaffin cells.

Sigma Aldrich - P202

Amino Acid Sequence
His-Ser-Asp-Gly-Ile-Phe-Thr-Asp-Ser-Tyr-Ser-Arg-Tyr-Arg-Lys-Gln-Met-Ala-Val-Lys-Lys-Tyr-Leu-Ala-Ala-Val-Leu-NH2