4-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{2-[(4-carbamimidamido-1-{[1-({1-[(1-{[({1-[({[1-(2-carbamoylpyrrolidin-1-yl)-3-hydroxy-1-oxobutan-2-yl]carbamoyl}methyl)carbamoyl]ethyl}carbamoyl)methyl]carbamoyl}-2-methylpropyl)carbamoyl]-2-carboxyethyl}carbamoyl)-2-hydroxypropyl]carbamoyl}butyl)carbamoyl]pyrrolidin-1-yl}-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamoyl]-2-hydroxypropyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pentyl}carbamoyl)-2-(1H-imidazol-5-yl)ethyl]carbamoyl}-3-methylbutyl)carbamoyl]-4-(2-{2-[2-(6-amino-2-{2-[2-(2-{[22-amino-7-(1-hydroxyethyl)-10,16-bis(hydroxymethyl)-19-methyl-13-(2-methylpropyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-3-methylbutanamido)-4-methylpentanamido]acetamido}hexanamido)-4-methylpentanamido]-3-hydroxypropanamido}-4-carbamoylbutanamido)butanoic acid

• ChemBase ID: 104068
• Molecular Formular: C145H240N42O46S2
• Molecular Mass: 3371.8409
• Monoisotopic Mass: 3369.71733041
• SMILES: NCCCCC(NC(=O)C(Cc1[nH]cnc1)NC(=O)C(CC(C)C)NC(=O)C(CCC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(CO)NC(=O)C(CC(C)C)NC(=O)C(CCCCN)NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1CSSCC(N)C(=O)NC(C)C(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C(C)O)C(=O)N1)C(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(C(C)O)C(=O)NC(Cc1ccc(O)cc1)C(=O)N1CCCC1C(=O)NC(CCCNC(=N)N)C(=O)NC(C(C)O)C(=O)NC(CC(=O)O)C(=O)NC(C(C)C)C(=O)NCC(=O)NC(C)C(=O)NCC(=O)NC(C(C)O)C(=O)N1CCCC1C(=O)N
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NCC(=O)NC(C(=O)N1CCCC1C(=O)N)C(O)C)C)C(C)C)CC(=O)O)C(O)C)CCCNC(=N)N)Cc1ccc(cc1)O)C(O)C)CCC(=O)N)CC(C)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(C(C)C)NC(=O)C1CSSCC(N)C(=O)NC(C)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C(O)C)CO)CC(C)C)CO)CC(C)C)CCCCN)CC(C)C)CO)CCC(=O)N)CCC(=O)O)CC(C)C)Cc1[nH]cnc1
• InChI: InChI=1S/C145H240N42O46S2/c1-66(2)48-89(173-139(228)111(72(13)14)182-136(225)100-64-235-234-63-82(148)119(208)161-74(16)118(207)176-97(60-188)134(223)171-93(52-70(9)10)130(219)178-99(62-190)135(224)185-114(77(19)193)142(231)179-100)120(209)157-58-106(199)162-83(28-21-23-43-146)121(210)168-92(51-69(7)8)129(218)177-98(61-189)133(222)166-86(37-40-103(149)196)123(212)164-88(39-42-108(201)202)124(213)170-91(50-68(5)6)128(217)172-94(54-80-56-154-65-159-80)131(220)163-84(29-22-24-44-147)122(211)169-90(49-67(3)4)127(216)165-87(38-41-104(150)197)126(215)184-113(76(18)192)141(230)175-96(53-79-33-35-81(195)36-34-79)143(232)187-47-27-32-102(187)137(226)167-85(30-25-45-155-145(152)153)125(214)183-112(75(17)191)140(229)174-95(55-109(203)204)132(221)181-110(71(11)12)138(227)158-57-105(198)160-73(15)117(206)156-59-107(200)180-115(78(20)194)144(233)186-46-26-31-101(186)116(151)205/h33-36,56,65-78,82-102,110-115,188-195H,21-32,37-55,57-64,146-148H2,1-20H3,(H2,149,196)(H2,150,197)(H2,151,205)(H,154,159)(H,156,206)(H,157,209)(H,158,227)(H,160,198)(H,161,208)(H,162,199)(H,163,220)(H,164,212)(H,165,216)(H,166,222)(H,167,226)(H,168,210)(H,169,211)(H,170,213)(H,171,223)(H,172,217)(H,173,228)(H,174,229)(H,175,230)(H,176,207)(H,177,218)(H,178,219)(H,179,231)(H,180,200)(H,181,221)(H,182,225)(H,183,214)(H,184,215)(H,185,224)(H,201,202)(H,203,204)(H4,152,153,155)
• InChIKey: ZLUQVFUSLGBVHE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{2-[(4-carbamimidamido-1-{[1-({1-[(1-{[({1-[({[1-(2-carbamoylpyrrolidin-1-yl)-3-hydroxy-1-oxobutan-2-yl]carbamoyl}methyl)carbamoyl]ethyl}carbamoyl)methyl]carbamoyl}-2-methylpropyl)carbamoyl]-2-carboxyethyl}carbamoyl)-2-hydroxypropyl]carbamoyl}butyl)carbamoyl]pyrrolidin-1-yl}-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamoyl]-2-hydroxypropyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pentyl}carbamoyl)-2-(1H-imidazol-5-yl)ethyl]carbamoyl}-3-methylbutyl)carbamoyl]-4-(2-{2-[2-(6-amino-2-{2-[2-(2-{[22-amino-7-(1-hydroxyethyl)-10,16-bis(hydroxymethyl)-19-methyl-13-(2-methylpropyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-3-methylbutanamido)-4-methylpentanamido]acetamido}hexanamido)-4-methylpentanamido]-3-hydroxypropanamido}-4-carbamoylbutanamido)butanoic acid
• IUPAC Traditional name: 4-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{2-[(4-carbamimidamido-1-{[1-({1-[(1-{[({1-[({[1-(2-carbamoylpyrrolidin-1-yl)-3-hydroxy-1-oxobutan-2-yl]carbamoyl}methyl)carbamoyl]ethyl}carbamoyl)methyl]carbamoyl}-2-methylpropyl)carbamoyl]-2-carboxyethyl}carbamoyl)-2-hydroxypropyl]carbamoyl}butyl)carbamoyl]pyrrolidin-1-yl}-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamoyl]-2-hydroxypropyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}-3-methylbutyl)carbamoyl]pentyl}carbamoyl)-2-(3H-imidazol-4-yl)ethyl]carbamoyl}-3-methylbutyl)carbamoyl]-4-(2-{2-[2-(6-amino-2-{2-[2-(2-{[22-amino-7-(1-hydroxyethyl)-10,16-bis(hydroxymethyl)-19-methyl-13-(2-methylpropyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-3-methylbutanamido)-4-methylpentanamido]acetamido}hexanamido)-4-methylpentanamido]-3-hydroxypropanamido}-4-carbamoylbutanamido)butanoic acid
• Synonyms: CALCITONIN; Calcitonin; Cys-Ala-Ser-Leu-Ser-Thr-Cys-Val-Leu-Gly-Lys-Leu-Ser-Gln-Glu-Leu-His-Lys-Leu-Gln-Thr-Tyr-Pro-Arg-Thr-Asp-Val-Gly-Ala-Gly-Thr-Pro-NH2 [Disulfide bridge: 1-7]; Thyrocalcitonin from chicken

Database IDs

• CAS Number: 100016-62-4
• PubChem SID: 162090997
• PubChem CID: 71299691

CALCULATED PROPERTIES

• Acid pKa: 3.3256662
• H Acceptors: 53
• H Donor: 49
• LogD (pH = 5.5): -30.485897
• LogD (pH = 7.4): -27.732786
• Log P: -25.757368
• Molar Refractivity: 843.4157 cm^3
• Polarizability: 327.31366 Å^3
• Polar Surface Area: 1418.87 Å^2
• Rotatable Bonds: 95
• 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

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C145H240N42O46S2

DETAILS

MP Biomedicals - 02154497

H2N-Cys-Ala-Ser-Leu-Ser-Thr-Cys- Val-Leu-Gly-Lys-Leu-Ser-Gln-Glu- Leu-His-Lys-Leu-Gln-Thr-Tyr-Pro- Arg-Thr-Asp-Val-Gly-Ala-Gly-Thr- Pro-NH2 Source/Species: Chicken

Sigma Aldrich - T9907

Biochem/physiol Actions
Hypocalcemic hormone produced by the parafollicular C cells of the thyroid or by the ultimobranchial bodies of nonmammalian vertebrates. Decreases blood calcium and phosphate due to inhibition of resorption by osteoblasts and osteocytes.
Other Notes
A 32 amino acid polypeptide, 8 of which are conserved across all species.

REFERENCES

• Kurihara, T. et al., Peptide Chemistry,