(2S)-2-{[(1R,4S,7S,13S,16R,21R,24R,27S,30S,33R,38R,44S)-21-amino-13-(carbamoylmethyl)-27-(2-carboxyethyl)-44-[(1R)-1-hydroxyethyl]-30-[(4-hydroxyphenyl)methyl]-4-methyl-3,6,12,15,22,25,28,31,40,43,46,51-dodecaoxo-18,19,35,36,48,49-hexathia-2,5,11,14,23,26,29,32,39,42,45,52-dodecaazatetracyclo[22.22.4.216,33.07,11]dopentacontan-38-yl]formamido}-3-(4-hydroxyphenyl)propanoic acid

• ChemBase ID: 130500
• Molecular Formular: C59H79N15O21S6
• Molecular Mass: 1526.73646
• Monoisotopic Mass: 1525.38992062
• SMILES: C[C@H]1C(=O)N[C@@H]2CSSC[C@H]3C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)CNC(=O)[C@@H](NC2=O)[C@@H](C)O)C(=O)N[C@@H](Cc2ccc(cc2)O)C(=O)O)C(=O)N[C@@H](CSSC[C@@H](C(=O)N3)N)C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N1)CC(=O)N)Cc1ccc(cc1)O)CCC(=O)O
• Canonical SMILES: OC(=O)CC[C@@H]1NC(=O)[C@@H]2CSSC[C@H]3NC(=O)[C@H](C)NC(=O)[C@H]4N(C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)Cc1ccc(cc1)O)CSSC[C@H](NC(=O)CNC(=O)[C@@H](NC3=O)[C@H](O)C)C(=O)N[C@H](C(=O)O)Cc1ccc(cc1)O)CSSC[C@@H](C(=O)N2)N)CC(=O)N)CCC4
• InChI: InChI=1S/C59H79N15O21S6/c1-26-47(82)69-41-25-101-99-22-38-52(87)65-33(13-14-45(80)81)49(84)66-34(16-28-5-9-30(76)10-6-28)50(85)71-40(54(89)72-39(23-97-96-20-32(60)48(83)70-38)53(88)67-35(18-43(61)78)58(93)74-15-3-4-42(74)56(91)63-26)24-100-98-21-37(64-44(79)19-62-57(92)46(27(2)75)73-55(41)90)51(86)68-36(59(94)95)17-29-7-11-31(77)12-8-29/h5-12,26-27,32-42,46,75-77H,3-4,13-25,60H2,1-2H3,(H2,61,78)(H,62,92)(H,63,91)(H,64,79)(H,65,87)(H,66,84)(H,67,88)(H,68,86)(H,69,82)(H,70,83)(H,71,85)(H,72,89)(H,73,90)(H,80,81)(H,94,95)/t26-,27+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,46-/m0/s1
• InChIKey: KXGCNMMJRFDFNR-WDRJZQOASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(1R,4S,7S,13S,16R,21R,24R,27S,30S,33R,38R,44S)-21-amino-13-(carbamoylmethyl)-27-(2-carboxyethyl)-44-[(1R)-1-hydroxyethyl]-30-[(4-hydroxyphenyl)methyl]-4-methyl-3,6,12,15,22,25,28,31,40,43,46,51-dodecaoxo-18,19,35,36,48,49-hexathia-2,5,11,14,23,26,29,32,39,42,45,52-dodecaazatetracyclo[22.22.4.2^1^6,^3^3.0^7,^1^1]dopentacontan-38-yl]formamido}-3-(4-hydroxyphenyl)propanoic acid
• IUPAC Traditional name: (2S)-2-{[(1R,4S,7S,13S,16R,21R,24R,27S,30S,33R,38R,44S)-21-amino-13-(carbamoylmethyl)-27-(2-carboxyethyl)-44-[(1R)-1-hydroxyethyl]-30-[(4-hydroxyphenyl)methyl]-4-methyl-3,6,12,15,22,25,28,31,40,43,46,51-dodecaoxo-18,19,35,36,48,49-hexathia-2,5,11,14,23,26,29,32,39,42,45,52-dodecaazatetracyclo[22.22.4.2^1^6,^3^3.0^7,^1^1]dopentacontan-38-yl]formamido}-3-(4-hydroxyphenyl)propanoic acid
• Brand Name: Linzess
• Synonyms: Linaclotide

Database IDs

• CAS Number: 851199-59-2
• PubChem SID: 162224779
• PubChem CID: 16158208
• ATC CODE: A06AX04
• KEGG ID: D09355
• Unique Ingredient Identifier: N0TXR0XR5X
• Wikipedia Title: Linaclotide

CALCULATED PROPERTIES

• Polarizability: 144.12267 Å^3
• Polar Surface Area: 573.91 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false
• Acid pKa: 3.058641
• H Acceptors: 22
• H Donor: 19
• LogD (pH = 5.5): -12.272248
• LogD (pH = 7.4): -13.968965
• Log P: -10.775399
• Molar Refractivity: 368.0006 cm^3

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Rx-only (US)
• Pregnancy Category: C (US)
• US Licence: Linaclotide