Penilactone - Compound Card

Penilactone

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Penilactone

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Lactone
    • Subclass: Macrolide
Canonical Smiles C[C@H]1CCC(=O)[C@@H]2CC(=O)c3c(CC(=O)O1)cc(cc3O2)O
InChI InChI=1S/C16H16O6/c1-8-2-3-11(18)13-7-12(19)16-9(5-15(20)21-8)4-10(17)6-14(16)22-13/h4,6,8,13,17H,2-3,5,7H2,1H3/t8-,13-/m0/s1
InChIKey FVRXJARCVLXBHQ-SDBXPKJASA-N
Formula C16H16O6
HBA 6
HBD 1
MW 304.3
Rotatable Bonds 0
TPSA 89.9
LogP 1.56
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 304.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium species Trichocomaceae Fungi 5073

Showing of synonyms

  • Aly AH, Debbab A, et al. (2011). NF kappa B inhibitors and antitrypanosomal metabolites from endophytic fungus Penicillium sp. isolated from Limonium tubiflorum. Bioorganic and Medicinal Chemistry,2011,19(1),414-421. [View] [PubMed]
Pubchem: 163015155

No compound-protein relationship available.

Structure

SMILES: c12c3cccc1OC(CC2=O)C(=O)CCCOC(=O)C3

Level: 0

Mol. Weight: 304.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.61
Plasma Protein Binding
51.3
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.3
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.47
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.29
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.88
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.92
Rat (Acute)
2.33
Rat (Chronic Oral)
2.14
Fathead Minnow
3.97
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
415.79
Hydration Free Energy
-8.05
Log(D) at pH=7.4
0.77
Log(P)
0.92
Log S
-3.54
Log(Vapor Pressure)
-7.87
Melting Point
264.81
pKa Acid
6.2
pKa Basic
4.73
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9532
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9532
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9507
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9507
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.9140
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.9140
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8513
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8513
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8012
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8012
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7999
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7999
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7884
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7884
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7799
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7799
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7785
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7785
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7668
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7668
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7638
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7638
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7539
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7539
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 3 0.7380
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 3 0.7380
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7373
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7373
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7252
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7252
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7243
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7243
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7232
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7232
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7221
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7221
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8RQP5 ISPF_THET8 Thermus thermophilus 3 0.7206
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8RQP5 ISPF_THET8 Thermus thermophilus 3 0.7206
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7173
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7173
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7099
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7099
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7097
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7097
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7096
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7096
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7080
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7080
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7068
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7068
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7035
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7035
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7026
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7026
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7011
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7011
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7006
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7006

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