Responsive image

Common name


Hyaluronic acid

IUPAC name


(2S,3S,4R,5R,6R)-3-{[(2S,3R,5S,6R)-4-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid

SMILES


CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@@H]1O[C@@H]([C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H]2NC(C)=O)[C@H](O)[C@H]1O)C(O)=O

Compound class


Adjuvants, Immunologic; Viscosupplements; Respiratory System; Ophthalmologicals; Sensory Organs; Musculo-Skeletal System; Cicatrizants; Preparations for Treatment of Wounds and Ulcers; Dermatologicals; Nasal Preparations; Viscoelastic Substances; Surgical Aids;

Therapeutic area


Used to treat knee pain in patients with joint inflammation (osteoarthritis). It is usually used in patients who have not responded to other treatments such as acetaminophen, exercise, or physical therapy. Hyaluronic acid may also be used in plastic surgery to reduce wrinkles on the face or as a filler in other parts of the body. May be used in ophthalmology to assist in the extraction of cataracts, the implantation of intraocular lenses, corneal transplants, glaucoma filtration, retinal attachment and in the treatment of dry eyes. Finally, hyaluronic acid is also used to coat the bladder lining in treating interstitial cystitis.

Common name


Hyaluronic acid

IUPAC name


(2S,3S,4R,5R,6R)-3-{[(2S,3R,5S,6R)-4-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid

SMILES


CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@@H]1O[C@@H]([C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H]2NC(C)=O)[C@H](O)[C@H]1O)C(O)=O

INCHI


InChI=1S/C28H44N2O23/c1-5(33)29-9-18(11(35)7(3-31)47-25(9)46)49-28-17(41)15(39)20(22(53-28)24(44)45)51-26-10(30-6(2)34)19(12(36)8(4-32)48-26)50-27-16(40)13(37)14(38)21(52-27)23(42)43/h7-22,25-28,31-32,35-41,46H,3-4H2,1-2H3,(H,29,33)(H,30,34)(H,42,43)(H,44,45)/t7-,8-,9-,10-,11-,12-,13+,14+,15-,16-,17-,18?,19?,20+,21+,22+,25-,26+,27-,28-/m1/s1

FORMULA


C28H44N2O23

Responsive image

Common name


Hyaluronic acid

IUPAC name


(2S,3S,4R,5R,6R)-3-{[(2S,3R,5S,6R)-4-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid

Molecular weight


776.649

clogP


-9.028

clogS


6.972

HBond Acceptor


23

HBond Donor


14

Total Polar
Surface Area


399.71

Number of Rings


4

Rotatable Bond


12

Drug ID Common name Structure CAS SMILE Frequency
FDBF00015 acetamide Responsive image NC(=O)C 0.0460
FDBF01595 (2R,5S)-tetrahydropyran-2,5-diol Responsive image O1CC(CCC1O)O 0.0007
FDBF01598 (3S)-tetrahydropyran-3-ol Responsive image O1CCCC(C1)O 0.0007
FDBF03678 (3R,4S)-tetrahydropyran-3,4-diol Responsive image OC1CCOCC1O 0.0007
FDBF03679 N-[(3R,5S)-5-hydroxytetrahydropyran-3-yl]acetamide Responsive image O=C(NC1COCC(C1)O)C 0.0003
FDBF03680 (2S,3S)-2-(hydroxymethyl)tetrahydropyran-3-ol Responsive image OCC1OCCCC1O 0.0003
6 , 1