Linaclotide acetateProduct ingredient forLinaclotide

Name

Linaclotide acetate

Drug Entry

Linaclotide

Linaclotide is an orally administered, peptide agonist of guanylate cyclase 2C for the treatment of irritable bowel syndrome. Chemically, it is a heterodetic cyclic peptide and consists of fourteen amino acids. The protein sequence is as follows: Cys Cys Glu Tyr Cys Cys Asn Pro Ala Cys Thr Gly Cys Tyr. There are three disulfide bonds which are located between Cys1 and Cys6; between Cys2 and Cys10; and between Cys5 and Cys13. FDA approved on August 30, 2012.

See full entry for Linaclotide

Accession Number

DBSALT000108

Structure

Similar Structures

Synonyms

Not Available

External IDs

MM-416775

UNII

NSF067KU1M

CAS Number

851199-60-5

Weight

Average: 1586.788
Monoisotopic: 1585.411048177

Chemical Formula

C₆₁H₈₃N₁₅O₂₃S₆

InChI Key

KWFNVZFWXXEJKL-YZDVLOIKSA-N

InChI

InChI=1S/C59H79N15O21S6.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t26-,27+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,46-;/m0./s1

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^{16,33}.0^{7,11}]dopentacontan-38-yl]formamido}-3-(4-hydroxyphenyl)propanoic acid; acetic acid

SMILES

CC(O)=O.[H][C@]1(CSSC[C@]2([H])NC(=O)[C@H](CC3=CC=C(O)C=C3)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H]3CSSC[C@H](NC(=O)[C@H](C)NC(=O)[C@@H]4CCCN4C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CSSC[C@H](N)C(=O)N3)NC2=O)C(=O)N[C@@]([H])([C@@H](C)O)C(=O)NCC(=O)N1)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O

External Links

PubChem Compound: 16158207
ChemSpider: 17314503
ChEMBL: CHEMBL3301676

Predicted Properties

Property	Value	Source
Water Solubility	0.701 mg/mL	ALOGPS
logP	-1.5	ALOGPS
logP	-11	Chemaxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.06	Chemaxon
pKa (Strongest Basic)	7.65	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	22	Chemaxon
Hydrogen Donor Count	19	Chemaxon
Polar Surface Area	573.91 Å²	Chemaxon
Rotatable Bond Count	13	Chemaxon
Refractivity	368 m³·mol^-1	Chemaxon
Polarizability	145.88 Å³	Chemaxon
Number of Rings	6	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Linaclotide acetateProduct ingredient forLinaclotide

Structure for Linaclotide acetate (DBSALT000108)