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    Chemistry

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    Also known as: Dermatan sulfate, Beta-heparin, Chondroitin sulfate b, 24967-94-0, (2r,3s,4s,5r,6r)-6-[(2r,3r,4r,5r,6r)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfonatooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate, Dermatan 4-sulfate
    Molecular Formula
    C14H21NO15S-2
    Molecular Weight
    475.4  g/mol
    InChI Key
    AVJBPWGFOQAPRH-FWMKGIEWSA-L
    Dermatan Sulfate
    A naturally occurring glycosaminoglycan found mostly in the skin and in connective tissue. It differs from CHONDROITIN SULFATE A (see CHONDROITIN SULFATES) by containing IDURONIC ACID in place of glucuronic acid, its epimer, at carbon atom 5. (from Merck, 12th ed)
    1 2D Structure

    Dermatan Sulfate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfonatooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
    2.1.2 InChI
    InChI=1S/C14H23NO15S/c1-3(17)15-5-10(9(30-31(24,25)26)4(2-16)27-13(5)23)28-14-8(20)6(18)7(19)11(29-14)12(21)22/h4-11,13-14,16,18-20,23H,2H2,1H3,(H,15,17)(H,21,22)(H,24,25,26)/p-2/t4-,5-,6+,7+,8-,9+,10-,11-,13-,14-/m1/s1
    2.1.3 InChI Key
    AVJBPWGFOQAPRH-FWMKGIEWSA-L
    2.1.4 Canonical SMILES
    CC(=O)NC1C(C(C(OC1O)CO)OS(=O)(=O)[O-])OC2C(C(C(C(O2)C(=O)[O-])O)O)O
    2.1.5 Isomeric SMILES
    CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O)CO)OS(=O)(=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](O2)C(=O)[O-])O)O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Beta Heparin

    2. Beta-heparin

    3. Chondroitin Sulfate B

    4. Dermatan Sulfate

    5. Sulfate B, Chondroitin

    6. Sulfate, Dermatan

    2.2.2 Depositor-Supplied Synonyms

    1. Dermatan Sulfate

    2. Beta-heparin

    3. Chondroitin Sulfate B

    4. 24967-94-0

    5. (2r,3s,4s,5r,6r)-6-[(2r,3r,4r,5r,6r)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfonatooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate

    6. Dermatan 4-sulfate

    7. Desmin 370

    8. Chondroitinsulfuric Acid

    9. Dermatan Hydrogen Sulfate

    10. Chondroitinsulfuric Acid B

    11. Chondroitin Sulfate Type B

    12. Mf 701 (polysaccharide)

    13. Chondroitinsulfuric Acid Type B

    14. Chondroitinsulfuric Acid, Type B

    15. Chondroitinsulfuric Acids, Type B

    16. Mf701

    17. Dermatan, Hydrogen Sulfate (ester)

    18. Einecs 246-552-8

    19. Ds 435

    20. Mf 701

    21. Dermatan Sulfate, Low Molecular Weight

    22. Dermatan 4'-sulfate

    23. 54328-33-5

    24. Dermatan Sulfate Polyanion

    25. Chebi:58465

    26. Yd58324

    27. Danaparoid Sodium - Mixture Of Dermatan Sulfate, Heparan Sulfate And Chondroitin Sulfate

    2.3 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 475.4 g/mol
    Molecular Formula C14H21NO15S-2
    XLogP3-4.3
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count5
    Exact Mass475.06319014 g/mol
    Monoisotopic Mass475.06319014 g/mol
    Topological Polar Surface Area273 Ų
    Heavy Atom Count31
    Formal Charge-2
    Complexity737
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    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

    Anticoagulants

    Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)

    4.2 ATC Code

    B - Blood and blood forming organs

    B01 - Antithrombotic agents

    B01A - Antithrombotic agents

    B01AX - Other antithrombotic agents

    B01AX04 - Dermatan sulfate

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