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

General Information of Drug (ID: DR2217)
Drug Name
ML-236B
Synonyms
Antibiotic ML 236B; Compactin (penicillium); ML 236 B; ML-236B; ML236B; Mevastatin; Mevastatin (Compactin); Mevastatin [INN]; Mevastatina; Mevastatina [INN-Spanish]; Mevastatine; Mevastatine [INN-French]; Mevastatinum; Mevastatinum [INN-Latin]; compactin; 1UQM1K0W9X; 73573-88-3; CCRIS 4505; CHEBI:34848; CHEMBL54440; CS 500; UNII-1UQM1K0W9X; [(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
Indication Hypertriglyceridaemia [ICD11: 5C80] Preclinical [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 390.5 Topological Polar Surface Area 72.8
Heavy Atom Count 28 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
64715
PubChem SID
7846932 ; 7978987 ; 8189253 ; 12015427 ; 14756488 ; 14780729 ; 17405315 ; 24278540 ; 24820212 ; 25819930 ; 26719712 ; 26759157 ; 43121594 ; 46386660 ; 47574453 ; 47944886 ; 49896293 ; 53777860 ; 53790805 ; 56468435 ; 57288790 ; 57315124 ; 71821891 ; 78233515 ; 85787615 ; 89850273 ; 90340823 ; 91614978 ; 92304233 ; 92308676 ; 92308746 ; 103241784 ; 103923731 ; 104331841 ; 117549691 ; 119525148 ; 121361574 ; 124659149 ; 124800281 ; 135021782 ; 135650602 ; 135727287 ; 135969249 ; 137101020 ; 142413177 ; 144089061 ; 144205093 ; 152134131 ; 160809187 ; 162023089
ChEBI ID
CHEBI:34848
CAS Number
73573-88-3
TTD Drug ID
D0J9GD
Formula
C23H34O5
Canonical SMILES
CCC(C)C(=O)OC1CCC=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O
InChI
1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
InChIKey
AJLFOPYRIVGYMJ-INTXDZFKSA-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
pravastatin DM006493
54687
Oxidation - 6-hydroxylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006984 ML-236B pravastatin Oxidation - 6-hydroxylation CYP105A3 [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 105A3 (cyp105A3) DMEN397 Streptomyces carbophilus
CPS2_STRCC
1.14.-.-
[2]
Cytochrome P450 105D7 (cyp105) DME1233 Streptomyces avermitilis
CYP28_STRAW
1.14.15.11
[3] , [4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [5]
⏷ Show the Full List of 15  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Cytochrome P450 105D7 (cyp105) DME1233 Km = 39.1 microM
CYP28_STRAW
[3] , [4]
References
1 Mevastatin, an HMG-CoA reductase inhibitor, reduces stroke damage and upregulates endothelial nitric oxide synthase in mice. Stroke. 2001 Apr;32(4):980-6.
2 Hydroxylation of Steroids by a Microbial Substrate-Promiscuous P450 Cytochrome (CYP105D7): Key Arginine Residues for Rational Design
3 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
4 Hydroxylation of Compactin (ML-236B) by CYP105D7 (SAV_7469) from Streptomyces avermitilis. J Microbiol Biotechnol. 2017 May 28;27(5):956-964.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.