Details of the Drug

General Information of Drug (ID: DM1LGKP)

Drug Name
Mevastatin
Synonyms
Mevastatin; compactin; 73573-88-3; ML-236B; Mevastatinum; Mevastatine; Mevastatina; Mevastatinum [INN-Latin]; Antibiotic ML 236B; Mevastatin [INN]; CS 500; Compactin (penicillium); Mevastatine [INN-French]; UNII-1UQM1K0W9X; ML 236 B; Mevastatina [INN-Spanish]; CCRIS 4505; 1UQM1K0W9X; CHEMBL54440; CHEBI:34848; [(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; Mevastatin (Compactin); ML236B
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 390.5
Logarithm of the Partition Coefficient (xlogp) 3.9
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C23H34O5
IUPAC Name
[(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
Canonical SMILES
CC[C@H](C)C(=O)O[C@H]1CCC=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O
InChI
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
Cross-matching ID
PubChem CID
64715
ChEBI ID
CHEBI:34848
CAS Number
73573-88-3
DrugBank ID
DB06693
TTD ID
D0J9GD
INTEDE ID
DR2217
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
HMG-CoA reductase (HMGCR) TTPADOQ HMDH_HUMAN Antagonist [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 105D7 (cyp105)
Main DME 		DECV2ME CYP28_STRAW Substrate [2], [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bone morphogenetic protein 2 (BMP2) OT23T37S BMP2_HUMAN Gene/Protein Processing [4]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [5]
Transforming protein RhoA (RHOA) OT6YOJ9N RHOA_HUMAN Post-Translational Modifications [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
HMG-CoA reductase (HMGCR) DTT HMGCR 1.01E-05 0.65 1.53
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Regulation of CYP2B6 and CYP3A expression by hydroxymethylglutaryl coenzyme A inhibitors in primary cultured human hepatocytes. Drug Metab Dispos. 2002 Dec;30(12):1400-5.
2 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
3 Hydroxylation of Compactin (ML-236B) by CYP105D7 (SAV_7469) from Streptomyces avermitilis. J Microbiol Biotechnol. 2017 May 28;27(5):956-964.
4 Compactin and simvastatin, but not pravastatin, induce bone morphogenetic protein-2 in human osteosarcoma cells. Biochem Biophys Res Commun. 2000 May 19;271(3):688-92. doi: 10.1006/bbrc.2000.2697.
5 A cell-based reporter gene assay for determining induction of CYP3A4 in a high-volume system. J Pharmacol Exp Ther. 2002 Oct;303(1):412-23.
6 Asbestos induces nitric oxide synthesis in mesothelioma cells via Rho signaling inhibition. Am J Respir Cell Mol Biol. 2007 Jun;36(6):746-56. doi: 10.1165/rcmb.2006-0011OC. Epub 2007 Feb 22.