3-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{2-[(3-carbamoyl-1-{[1-({1-[(1-{[({1-[({[1-(2-carbamoylpyrrolidin-1-yl)-1-oxopropan-2-yl]carbamoyl}methyl)carbamoyl]-2-methylpropyl}carbamoyl)methyl]carbamoyl}-2-methylbutyl)carbamoyl]ethyl}carbamoyl)-2-hydroxypropyl]carbamoyl}propyl)carbamoyl]pyrrolidin-1-yl}-1-oxo-3-phenylpropan-2-yl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-phenylethyl)carbamoyl]pentyl}carbamoyl)-2-carbamoylethyl]carbamoyl}-2-phenylethyl)carbamoyl]-3-(2-{2-[2-(2-{2-[2-(2-{[22-amino-16-(carbamoylmethyl)-7-(1-hydroxyethyl)-10-(hydroxymethyl)-13-(2-methylpropyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-4-(methylsulfanyl)butanamido)-4-methylpentanamido]acetamido}-3-hydroxybutanamido)-3-(4-hydroxyphenyl)propanamido]-3-hydroxybutanamido}-4-carbamoylbutanamido)propanoic acid

• ChemBase ID: 103564
• Molecular Formular: C151H226N40O45S3
• Molecular Mass: 3417.84614
• Monoisotopic Mass: 3415.57878833
• SMILES: CCC(C)C(NC(=O)C(C)NC(=O)C(NC(=O)C(CCC(=O)N)NC(=O)C1CCCN1C(=O)C(Cc1ccccc1)NC(=O)C(NC(=O)C(Cc1c[nH]cn1)NC(=O)C(Cc1ccccc1)NC(=O)C(CCCCN)NC(=O)C(CC(=O)N)NC(=O)C(Cc1ccccc1)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C(NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(NC(=O)CNC(=O)C(CC(C)C)NC(=O)C(CCSC)NC(=O)C1CSSCC(N)C(=O)NCC(=O)NC(CC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C(C)O)C(=O)N1)C(C)O)C(C)O)C(C)O)C(C)O)C(=O)NCC(=O)NC(C(C)C)C(=O)NCC(=O)NC(C)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)C(C)C)C(CC)C)C)C(O)C)CCC(=O)N)Cc1ccccc1)C(O)C)Cc1nc[nH]c1)Cc1ccccc1)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(O)C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C1CSSCC(N)C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C(O)C)CO)CC(C)C)CC(=O)N)CCSC)CC(C)C)Cc1ccc(cc1)O)CCC(=O)N)CC(=O)O)Cc1ccccc1)CC(=O)N
• InChI: InChI=1S/C151H226N40O45S3/c1-17-75(8)118(144(229)163-67-114(205)183-117(74(6)7)143(228)162-64-112(203)165-77(10)150(235)190-50-29-38-106(190)124(158)209)185-125(210)76(9)166-145(230)120(79(12)194)186-131(216)92(45-47-109(155)200)170-142(227)107-39-30-51-191(107)151(236)103(58-85-35-25-20-26-36-85)180-148(233)122(81(14)196)188-139(224)99(59-87-63-159-71-164-87)176-133(218)96(55-83-31-21-18-22-32-83)174-128(213)90(37-27-28-49-152)168-136(221)101(61-111(157)202)177-134(219)97(56-84-33-23-19-24-34-84)175-137(222)102(62-116(207)208)178-129(214)91(44-46-108(154)199)171-147(232)121(80(13)195)187-138(223)98(57-86-40-42-88(198)43-41-86)179-146(231)119(78(11)193)184-115(206)66-161-127(212)94(53-72(2)3)172-130(215)93(48-52-237-16)169-141(226)105-70-239-238-69-89(153)126(211)160-65-113(204)167-100(60-110(156)201)135(220)173-95(54-73(4)5)132(217)181-104(68-192)140(225)189-123(82(15)197)149(234)182-105/h18-26,31-36,40-43,63,71-82,89-107,117-123,192-198H,17,27-30,37-39,44-62,64-70,152-153H2,1-16H3,(H2,154,199)(H2,155,200)(H2,156,201)(H2,157,202)(H2,158,209)(H,159,164)(H,160,211)(H,161,212)(H,162,228)(H,163,229)(H,165,203)(H,166,230)(H,167,204)(H,168,221)(H,169,226)(H,170,227)(H,171,232)(H,172,215)(H,173,220)(H,174,213)(H,175,222)(H,176,218)(H,177,219)(H,178,214)(H,179,231)(H,180,233)(H,181,217)(H,182,234)(H,183,205)(H,184,206)(H,185,210)(H,186,216)(H,187,223)(H,188,224)(H,189,225)(H,207,208)
• InChIKey: LDVRMNJZLWXJPL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{2-[(3-carbamoyl-1-{[1-({1-[(1-{[({1-[({[1-(2-carbamoylpyrrolidin-1-yl)-1-oxopropan-2-yl]carbamoyl}methyl)carbamoyl]-2-methylpropyl}carbamoyl)methyl]carbamoyl}-2-methylbutyl)carbamoyl]ethyl}carbamoyl)-2-hydroxypropyl]carbamoyl}propyl)carbamoyl]pyrrolidin-1-yl}-1-oxo-3-phenylpropan-2-yl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-phenylethyl)carbamoyl]pentyl}carbamoyl)-2-carbamoylethyl]carbamoyl}-2-phenylethyl)carbamoyl]-3-(2-{2-[2-(2-{2-[2-(2-{[22-amino-16-(carbamoylmethyl)-7-(1-hydroxyethyl)-10-(hydroxymethyl)-13-(2-methylpropyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-4-(methylsulfanyl)butanamido)-4-methylpentanamido]acetamido}-3-hydroxybutanamido)-3-(4-hydroxyphenyl)propanamido]-3-hydroxybutanamido}-4-carbamoylbutanamido)propanoic acid
• IUPAC Traditional name: 3-[(1-{[1-({5-amino-1-[(1-{[1-({1-[(1-{2-[(3-carbamoyl-1-{[1-({1-[(1-{[({1-[({[1-(2-carbamoylpyrrolidin-1-yl)-1-oxopropan-2-yl]carbamoyl}methyl)carbamoyl]-2-methylpropyl}carbamoyl)methyl]carbamoyl}-2-methylbutyl)carbamoyl]ethyl}carbamoyl)-2-hydroxypropyl]carbamoyl}propyl)carbamoyl]pyrrolidin-1-yl}-1-oxo-3-phenylpropan-2-yl)carbamoyl]-2-hydroxypropyl}carbamoyl)-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-2-phenylethyl)carbamoyl]pentyl}carbamoyl)-2-carbamoylethyl]carbamoyl}-2-phenylethyl)carbamoyl]-3-(2-{2-[2-(2-{2-[2-(2-{[22-amino-16-(carbamoylmethyl)-7-(1-hydroxyethyl)-10-(hydroxymethyl)-13-(2-methylpropyl)-6,9,12,15,18,21-hexaoxo-1,2-dithia-5,8,11,14,17,20-hexaazacyclotricosan-4-yl]formamido}-4-(methylsulfanyl)butanamido)-4-methylpentanamido]acetamido}-3-hydroxybutanamido)-3-(4-hydroxyphenyl)propanamido]-3-hydroxybutanamido}-4-carbamoylbutanamido)propanoic acid
• Synonyms: Calcitonin; Cys-Gly-Asn-Leu-Ser-Thr-Cys-Met-Leu-Gly-Thr-Tyr-Thr-Gln-Asp-Phe-Asn-Lys-Phe-His-Thr-Phe-Pro-Gln-Thr-Ala-Ile-Gly-Val-Gly-Ala-Pro-NH₂; CALCITONIN

Database IDs

• CAS Number: 21215-62-3
• EC Number: 244-276-2
• PubChem SID: 162091000
• PubChem CID: 16161965

CALCULATED PROPERTIES

• Acid pKa: 3.5191667
• H Acceptors: 48
• H Donor: 45
• LogD (pH = 5.5): -24.040112
• LogD (pH = 7.4): -21.648787
• Log P: -21.30954
• Molar Refractivity: 849.9439 cm^3
• Polarizability: 333.61234 Å^3
• Polar Surface Area: 1359.6 Å^2
• Rotatable Bonds: 91
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02152143

Source/Species: Human
Contains a disulfide bond between Cys1 and Cys7.
A synthetic hormone that possesses hypocalcemic and immunological activity.

REFERENCES

• Nakagawa, Y., et al., Peptide Chemistry, 189, (1977).