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    Chemistry

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    Also known as: Dolcanatide [usan], Unii-wu977t914k, Gtpl10011, Wu977t914k, Hy-p3499, 1092457-65-2
    Molecular Formula
    C65H104N18O26S4
    Molecular Weight
    1681.9  g/mol
    InChI Key
    NSPHQWLKCGGCQR-HLHYUOOASA-N
    Dolcanatide
    Dolcanatide is an orally administered analog of the human endogenous natriuretic hormone uroguanylin and guanylate cyclase C (GC-C) agonist, with potential laxative, anti-nociceptive and anti-inflammatory activities. Upon administration, dolcanatide, by mimicking uroguanylin, binds to and activates GC-C locally on endothelial cells in the gastrointestinal (GI) tract, without entering the systemic circulation. Activation of GC-C results in an increase in cyclic guanosine monophosphate (cGMP). Increased concentrations of cGMP lead to the activation of the anion channel cystic fibrosis transmembrane conductance regulator (CFTR). CFTR activation increases the secretion of negatively charged ions, particularly chloride and bicarbonate, into the GI tract lumen, which further drives sodium ions and then water into the lumen. This leads to increased fluid secretion in the GI tract, accelerated transit and changes in stool consistency. In addition, ion channel modulation may decrease muscle contractions and the activity of pain-sensing nerves, thereby decreasing intestinal pain. Also, GC-C may inhibit the secretion of pro-inflammatory cytokines, which may ameliorate GI inflammation. Uroguanylin, a naturally occurring human GI peptide, is a ligand for GC-C and plays a key role in anti-inflammatory processes in the GI tract.
    1 2D Structure

    Dolcanatide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R)-2-[[(1R,4S,7S,10S,13S,16R,19S,22S,25R,32S,38R)-10-(2-amino-2-oxoethyl)-25-[[(2S)-4-carboxy-2-[[(2S)-3-carboxy-2-[[(2R)-2,4-diamino-4-oxobutanoyl]amino]propanoyl]amino]butanoyl]amino]-22-(2-carboxyethyl)-32-[(1R)-1-hydroxyethyl]-4-methyl-19-(2-methylpropyl)-3,6,9,12,15,18,21,24,30,33,36-undecaoxo-7,13-di(propan-2-yl)-27,28,40,41-tetrathia-2,5,8,11,14,17,20,23,31,34,37-undecazabicyclo[14.13.13]dotetracontane-38-carbonyl]amino]-4-methylpentanoic acid
    2.1.2 InChI
    InChI=1S/C65H104N18O26S4/c1-25(2)15-34-55(98)80-41-24-113-110-21-38(58(101)77-37(65(108)109)16-26(3)4)71-44(87)20-69-62(105)50(30(10)84)83-61(104)40(78-51(94)29(9)70-63(106)48(27(5)6)81-57(100)35(18-43(68)86)76-64(107)49(28(7)8)82-60(41)103)23-112-111-22-39(59(102)73-32(53(96)75-34)11-13-45(88)89)79-54(97)33(12-14-46(90)91)72-56(99)36(19-47(92)93)74-52(95)31(66)17-42(67)85/h25-41,48-50,84H,11-24,66H2,1-10H3,(H2,67,85)(H2,68,86)(H,69,105)(H,70,106)(H,71,87)(H,72,99)(H,73,102)(H,74,95)(H,75,96)(H,76,107)(H,77,101)(H,78,94)(H,79,97)(H,80,98)(H,81,100)(H,82,103)(H,83,104)(H,88,89)(H,90,91)(H,92,93)(H,108,109)/t29-,30+,31+,32-,33-,34-,35-,36-,37+,38-,39-,40-,41-,48-,49-,50-/m0/s1
    2.1.3 InChI Key
    NSPHQWLKCGGCQR-HLHYUOOASA-N
    2.1.4 Canonical SMILES
    CC1C(=O)NC2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(NC(=O)CNC(=O)C(NC2=O)C(C)O)C(=O)NC(CC(C)C)C(=O)O)C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)C(C)C)CC(=O)N)C(C)C)CC(C)C)CCC(=O)O)NC(=O)C(CCC(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CC(=O)N)N
    2.1.5 Isomeric SMILES
    C[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=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](CC(C)C)C(=O)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(C)C)CC(=O)N)C(C)C)CC(C)C)CCC(=O)O)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@@H](CC(=O)N)N
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Sp-333

    2.2.2 Depositor-Supplied Synonyms

    1. Dolcanatide [usan]

    2. Unii-wu977t914k

    3. Gtpl10011

    4. Wu977t914k

    5. Hy-p3499

    6. 1092457-65-2

    7. D-leucine, D-asparaginyl-l-alpha-aspartyl-l-alpha-glutamyl-l-cysteinyl-l-alpha-glutamyl-l-leucyl-l-cysteinyl-l-valyl-l-asparaginyl-l-valyl-l-alanyl-l-cysteinyl-l-threonylglycyl-l-cysteinyl-, Cyclic (4->12),(7->15)-bis(disulfide)

    8. Cs-0615000

    2.3 Create Date
    2015-08-15
    3 Chemical and Physical Properties
    Molecular Weight 1681.9 g/mol
    Molecular Formula C65H104N18O26S4
    XLogP3-8.2
    Hydrogen Bond Donor Count23
    Hydrogen Bond Acceptor Count31
    Rotatable Bond Count28
    Exact Mass1680.6252002 g/mol
    Monoisotopic Mass1680.6252002 g/mol
    Topological Polar Surface Area819 Ų
    Heavy Atom Count113
    Formal Charge0
    Complexity3490
    Isotope Atom Count0
    Defined Atom Stereocenter Count16
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Guanylyl Cyclase C Agonists

    Compunds that bind to and activate GUANYLYL CYCLASE-C RECEPTORS. (See all compounds classified as Guanylyl Cyclase C Agonists.)

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