Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0317)
Drug Name
Chondroitin sulfate
Synonyms
Chondritinsulfate; Chondritinsulphate; Chondroitin 4 and 6 sulfate; Chondroitin 4-sulfate; Chondroitin 6-sulfate; Chondroitin polysulfate; Chondroitin sulfate; Chondroitin sulfuric acid; Chondroitin sulfuric acids; Chondroitin sulphate; Chondroitin, CHONDROITIN SULFATES; hydrogen sulfate; Chondroitine sulfate; Chondroitinsulfate C; Chondroitinsulfuric acids; Chondron; Chonsurid; Condrosan; Condrosulf; Sodium chondroitin sulfate; Structum; Uropol S; chondroitin sulfate C; 9007-28-7; EINECS 232-696-9; Gepan; UNII-6IC1M3OG5Z
Indication Osteoarthritis [ICD11: FA00] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 463.37 Topological Polar Surface Area 267
Heavy Atom Count 30 Rotatable Bond Count 6
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 15
Cross-matching ID
PubChem CID
24766
CAS Number
9007-28-7
Formula
C13H21NO15S
Canonical SMILES
CC(=O)NC1C(C(C(OC1O)OS(=O)(=O)O)O)OC2C(C(C(C(O2)C(=O)O)O)O)O
InChI
1S/C13H21NO15S/c1-2(15)14-3-8(7(19)13(28-11(3)22)29-30(23,24)25)26-12-6(18)4(16)5(17)9(27-12)10(20)21/h3-9,11-13,16-19,22H,1H3,(H,14,15)(H,20,21)(H,23,24,25)/t3-,4+,5+,6-,7-,8-,9+,11-,12-,13-/m1/s1
InChIKey
KXKPYJOVDUMHGS-OSRGNVMNSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Cs_a_deg1 DM003151 N. A. Hydrolysis - Hydrolysis 1 [3]
Cs_a_deg4 DM003130 N. A. Hydrolysis - Hydrolysis 1 [3]
Cs_e_deg1 DM003152 N. A. Hydrolysis - Hydrolysis 1 [3]
Cs_e_deg5 DM003153 N. A. Hydrolysis - Hydrolysis 1 [3]
D-glucuronate DM003133 N. A. Hydrolysis - Hydrolysis 1 [3]
Galactose DM003154
6036
Hydrolysis - Hydrolysis 1 [3]
Sulfate DM003142
1117
Hydrolysis - Hydrolysis 1 [3]
Xylose DM003155
135191
Hydrolysis - Hydrolysis 1 [3]
Cs_a_deg2 DM003146 N. A. Hydrolysis - Hydrolysis 2 [3]
Cs_a_deg5 DM003147 N. A. Hydrolysis - Hydrolysis 2 [3]
Cs_b_deg2 DM003143 N. A. Hydrolysis - Hydrolysis 2 [3]
Cs_c_deg2 DM003148 N. A. Hydrolysis - Hydrolysis 2 [3]
Cs_c_deg5 DM003139 N. A. Hydrolysis - Hydrolysis 2 [3]
Cs_d_deg2 DM003141 N. A. Hydrolysis - Hydrolysis 2 [3]
Cs_d_deg6 DM003131 N. A. Hydrolysis - Hydrolysis 2 [3]
Cs_e_deg3 DM003149 N. A. Hydrolysis - Hydrolysis 2 [3]
Cs_e_deg7 DM003150 N. A. Hydrolysis - Hydrolysis 2 [3]
N-acetyl-D-galactosamine DM003145
35717
Hydrolysis - Hydrolysis 2 [3]
Cs_a_deg3 DM003134 N. A. Hydrolysis - Hydrolysis 3 [3]
Cs_b_deg3 DM003144 N. A. Hydrolysis - Hydrolysis 3 [3]
Cs_c_deg3 DM003135 N. A. Hydrolysis - Hydrolysis 3 [3]
Cs_c_deg5 DM003139 N. A. Hydrolysis - Hydrolysis 3 [3]
Cs_d_deg3 DM003132 N. A. Hydrolysis - Hydrolysis 3 [3]
Cs_d_deg6 sulfate DM003140 N. A. Hydrolysis - Hydrolysis 3 [3]
D-glucuronate DM003133 N. A. Hydrolysis - Hydrolysis 3 [3]
L-iduronic acid DM003138
19770757
Hydrolysis - Hydrolysis 3 [3]
Sulfate DM003142
1117
Hydrolysis - Hydrolysis 3 [3]
Cs_a_deg3 DM003134 N. A. Hydrolysis - Hydrolysis 4 [3]
Cs_c_deg3 DM003135 N. A. Hydrolysis - Hydrolysis 4 [3]
Cs_d_deg4 DM003136 N. A. Hydrolysis - Hydrolysis 4 [3]
Cs_e_deg4 DM003137 N. A. Hydrolysis - Hydrolysis 4 [3]
D-glucuronate DM003133 N. A. Hydrolysis - Hydrolysis 4 [3]
⏷ Show the Full List of 32  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003570 Chondroitin sulfate Cs_a_deg4 Hydrolysis - Hydrolysis GALNS [3]
MR003599 Chondroitin sulfate Cs_a_deg1 Hydrolysis - Hydrolysis GALNS [3]
MR003600 Chondroitin sulfate Cs_e_deg1 Hydrolysis - Hydrolysis GALNS [3]
MR003601 Chondroitin sulfate Cs_e_deg5 Hydrolysis - Hydrolysis GALNS [3]
MR003602 Chondroitin sulfate Sulfate Hydrolysis - Hydrolysis GALNS [3]
MR003603 Chondroitin sulfate D-glucuronate Hydrolysis - Hydrolysis Unclear [3]
MR003604 Chondroitin sulfate Galactose Hydrolysis - Hydrolysis Unclear [3]
MR003605 Chondroitin sulfate Xylose Hydrolysis - Hydrolysis Unclear [3]
MR003571 Cs_a_deg4 Cs_d_deg6 Hydrolysis - Hydrolysis HEXB [3]
MR003582 Cs_a_deg4 Cs_d_deg2 Hydrolysis - Hydrolysis HEXB [3]
MR003589 Cs_a_deg4 Cs_b_deg2 Hydrolysis - Hydrolysis uidA [3]
MR003592 Cs_a_deg4 N-acetyl-D-galactosamine Hydrolysis - Hydrolysis HEXB [3]
MR003593 Cs_a_deg4 Cs_a_deg2 Hydrolysis - Hydrolysis HEXB [3]
MR003594 Cs_a_deg4 Cs_a_deg5 Hydrolysis - Hydrolysis HEXB [3]
MR003595 Cs_a_deg4 Cs_c_deg2 Hydrolysis - Hydrolysis HEXB [3]
MR003596 Cs_a_deg4 Cs_c_deg5 Hydrolysis - Hydrolysis HEXB [3]
MR003597 Cs_a_deg4 Cs_e_deg3 Hydrolysis - Hydrolysis HEXB [3]
MR003598 Cs_a_deg4 Cs_e_deg7 Hydrolysis - Hydrolysis HEXB [3]
MR003590 Cs_b_deg2 Cs_b_deg3 Hydrolysis - Hydrolysis IDS [3]
MR003591 Cs_b_deg2 Sulfate Hydrolysis - Hydrolysis IDS [3]
MR003583 Cs_d_deg2 Cs_c_deg5 Hydrolysis - Hydrolysis GALNS [3]
MR003584 Cs_d_deg2 Cs_d_deg3 Hydrolysis - Hydrolysis GALNS [3]
MR003585 Cs_d_deg2 Sulfate Hydrolysis - Hydrolysis GALNS [3]
MR003586 Cs_d_deg2 D-glucuronate Hydrolysis - Hydrolysis uidA [3]
MR003587 Cs_d_deg2 Cs_a_deg3 Hydrolysis - Hydrolysis uidA [3]
MR003588 Cs_d_deg2 Cs_c_deg3 Hydrolysis - Hydrolysis uidA [3]
MR003572 Cs_d_deg6 Cs_d_deg3 Hydrolysis - Hydrolysis SGSH [3]
MR003578 Cs_d_deg6 L-iduronic acid Hydrolysis - Hydrolysis IDUA [3]
MR003579 Cs_d_deg6 Cs_a_deg3 Hydrolysis - Hydrolysis IDUA [3]
MR003580 Cs_d_deg6 Cs_c_deg5 Hydrolysis - Hydrolysis SGSH [3]
MR003581 Cs_d_deg6 Cs_d_deg6 sulfate Hydrolysis - Hydrolysis SGSH [3]
MR003573 Cs_d_deg3 D-glucuronate Hydrolysis - Hydrolysis GUSB [3]
MR003574 Cs_d_deg3 Cs_a_deg3 Hydrolysis - Hydrolysis GUSB [3]
MR003575 Cs_d_deg3 Cs_c_deg3 Hydrolysis - Hydrolysis GUSB [3]
MR003576 Cs_d_deg3 Cs_d_deg4 Hydrolysis - Hydrolysis GUSB [3]
MR003577 Cs_d_deg3 Cs_e_deg4 Hydrolysis - Hydrolysis GUSB [3]
⏷ Show the Full List of 36 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alpha-L-iduronidase (IDUA) DME0104 Homo sapiens
IDUA_HUMAN
3.2.1.76
[2]
Arylsulfatase B (ARSB) DME0105 Homo sapiens
ARSB_HUMAN
3.1.6.12
[2]
Beta-glucuronidase (GUSB) DME0106 Homo sapiens
BGLR_HUMAN
3.2.1.31
[2]
Beta-glucuronidase (uidA) DME1042 Lactobacillus sakei
A0A2A5L2J1_LACRH
3.2.1.31
[3]
Chondroitin 6-sulfotransferase (CHST3) DME0632 Homo sapiens
CHST3_HUMAN
2.8.2.17
[4]
Hyaluronate lyase (hyaL) DME1240 Streptobacillus moniliformis
D1AWD4_STRM9
4.2.2.1
[5] , [6]
Hyaluronoglucosaminidase (nagH) DME1241 Treponema vincentii
NAGH_CLOPE
3.2.1.35
[7] , [8]
Iduronate 2-sulfatase (IDS) DME0108 Homo sapiens
IDS_HUMAN
3.1.6.13
[2]
N-acetyl-beta-glucosaminidase beta (HEXB) DME0107 Homo sapiens
HEXB_HUMAN
3.2.1.52
[2]
N-acetylgalactosamine-7-sulfatase (GALNS) DMEN087 Homo sapiens
GALNS_HUMAN
3.1.6.4
[3]
N-sulphoglucosamine sulphohydrolase (SGSH) DMEN088 Homo sapiens
SPHM_HUMAN
3.10.1.1
[3]
Unclear metabolic mechanism (DME-unclear) DME1263 Desulfovibrio piger Not Available Not Available [9]
⏷ Show the Full List of 12  DME(s)
References
1 ClinicalTrials.gov (NCT01233739) Chondroitin Sulphate Treatment Efficacy in Rhizarthrosis..
2 MFN human ref: Chondroitin sulfate degradation.
3 DrugBank(Pharmacology-Metabolism):Chondroitin?sulfate
4 Variants in chondroitin sulfate metabolism genes in thrombotic storm. Thromb Res. 2018 Jan;161:43-51.
5 A bacterial ABC transporter enables import of mammalian host glycosaminoglycans. Sci Rep. 2017 Apr 21;7(1):1069.
6 A case of Streptobacillus moniliformis infection with cutaneous leukocytoclastic vasculitis. Acta Med Okayama. 2016 Oct;70(5):377-381. Case Reports
7 An extracellular enzyme with hyaluronidase and chondroitinase activities from some oral anaerobic spirochaetes. Microbiology. 1996 Sep;142 ( Pt 9):2567-76.
8 Identification of a Treponema denticola OppA homologue that binds host proteins present in the subgingival environment. Infect Immun. 2000 Apr;68(4):1884-92.
9 Metabolic niche of a prominent sulfate-reducing human gut bacterium. Proc Natl Acad Sci U S A. 2013 Aug 13;110(33):13582-7.

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