Secondary metabolite: Lovastatin



Lovastatin
Summary
Molecular formula: C24H36O5
SMILES: CC[C@@H](C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
InChI: InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKey: PCZOHLXUXFIOCF-BXMDZJJMSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Lactones
Sub class: Delta valerolactones
Synonymous chemical names:
lovastatin, monacolin k
Chemical structure download



Lovastatin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 404.55
Log P RDKit 4.2
Topological polar surface area (Å2) RDKit 72.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 18
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.75
Shape complexity RDKit 0.75
Number of rotatable bonds SwissADME 7
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3



Lovastatin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.67



Lovastatin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.74
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No



Lovastatin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000199280AQP2800
ENSP00000200676CETP818
ENSP00000212015SIRT1800
ENSP00000215832MAPK1700
ENSP00000216117HMOX1824
ENSP00000220584FDFT1914
ENSP00000220616TG762
ENSP00000220809PLAT815
ENSP00000221930TGFB1800
ENSP00000222982CYP3A5864
ENSP00000225688RASD1900
ENSP00000226730IL2800
ENSP00000233242APOB988
ENSP00000236850APOA1915
ENSP00000241261TNFSF10700
ENSP00000251849RAF1900
ENSP00000252486APOE853
ENSP00000256078KRAS728
ENSP00000256442CCNB1800
ENSP00000256857GRP800
ENSP00000256958SLCO1B1744
ENSP00000260682CYP2C9965
ENSP00000261366LMNB1700
ENSP00000261596LPIN2700
ENSP00000262507COQ9815
ENSP00000263025MAPK3726
ENSP00000263817ABCB11700
ENSP00000263923KDR800
ENSP00000264047SLC5A7800
ENSP00000264832ICAM1828
ENSP00000265164CASP6700
ENSP00000265627PON3700
ENSP00000265724ABCB1950
ENSP00000266970CDK2752
ENSP00000267163RB1700
ENSP00000270202AKT1947
ENSP00000272233RHOB912
ENSP00000273668EAF2700
ENSP00000275493EGFR816
ENSP00000279593800
ENSP00000287908STEAP2729
ENSP00000287936HMGCR999
ENSP00000296871CSF2800
ENSP00000297494NOS3926
ENSP00000301645CYP7A1909
ENSP00000302150PRL800
ENSP00000307786CYCS814
ENSP00000308227HMGA1880
ENSP00000309845HRAS953
ENSP00000311032CASP3985
ENSP00000312664CASP2700
ENSP00000320709ADIPOQ800
ENSP00000324806GSK3B700
ENSP00000327251NOS2733
ENSP00000330237CASP9700
ENSP00000333568PRKD1800
ENSP00000337450CYP3A7821
ENSP00000337701PNPLA2800
ENSP00000337915CYP3A4988
ENSP00000338018HIF1A800
ENSP00000340210CD59800
ENSP00000340913TRPC6800
ENSP00000342007CYP1A2804
ENSP00000348069SREBF1850
ENSP00000348461RAC1742
ENSP00000349252ITGAL958
ENSP00000349588ANK2700
ENSP00000351273CASP8700
ENSP00000352516DNMT1800
ENSP00000353483MAPK8818
ENSP00000354476SREBF2960
ENSP00000357075TAGLN2800
ENSP00000357283LMNA900
ENSP00000358414HMGCS2784
ENSP00000358548NRAS700
ENSP00000360317CYP2C8736
ENSP00000361125VEGFA819
ENSP00000365435TNFRSF1B800
ENSP00000367851CYBB733
ENSP00000368104BMP2822
ENSP00000369050CYP1A1800
ENSP00000379213PTHLH800
ENSP00000384515PARVB700
ENSP00000387699CREB1800
ENSP00000400175RHOA919
ENSP00000405252AKAP7700
ENSP00000430432HDAC2800
ENSP00000435591MUC5AC800
ENSP00000454071LDLR982
ENSP00000463999AURKB800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interactions.

Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo