Meleagrin - Compound Card

Meleagrin

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Meleagrin

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CON1c2ccccc2[C@]2([C@]31NC(=O)/C(=C\c1cnc[nH]1)/N3C(=O)C(=C2)O)C(C=C)(C)C
InChI InChI=1S/C23H23N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-13,29H,1H2,2-4H3,(H,24,25)(H,26,30)/b17-10+/t22-,23-/m0/s1
InChIKey JTJJJLSLKZFEPJ-ZAYCRUKZSA-N
Formula C23H23N5O4
HBA 6
HBD 3
MW 433.47
Rotatable Bonds 4
TPSA 110.79
LogP 2.35
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 433.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Emericella dentata Trichocomaceae Fungi 286160
2 Penicillium chrysogenum Trichocomaceae Fungi 5076

Showing of synonyms

  • Hamed A, Abdel-Razek A.S, et al. (2021). Meleagrin from marine fungus Emericella dentata Nq45: crystal structure and diverse biological activity studies. Nat Prod Res,2021,35(21),3830-3838. [View] [PubMed]
  • Mady M.S, Mohyeldin M.M, et al. (2016). The indole alkaloid meleagrin, from the olive tree endophytic fungus Penicillium chrysogenum, as a novel lead for the control of c-Metdependent breast cancer proliferation, migration and invasion. Bioorganic & Medicinal Chemistry, 2016,24(2),113–122. [View] [PubMed]
Pubchem: 23728435
Nmrshiftdb2: 70013044
Pdb Ligand: 9Z1

No compound-protein relationship available.

Structure

SMILES: [nH]1cncc1C=C(C(=O)N2)N3C(=O)C=CC(C234)c5c(N4)cccc5

Level: 1

Mol. Weight: 433.47 g/mol

Structure

SMILES: N1C(=O)C(=C)N2C(=O)C=CC(C123)c4c(N3)cccc4

Level: 0

Mol. Weight: 433.47 g/mol

Structure

SMILES: c1c[nH]cn1

Level: 0

Mol. Weight: 433.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.4
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.160
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.28

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
89.31
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.310
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.860
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.380
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.290
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-131.940
Rat (Acute)
2.420
Rat (Chronic Oral)
2.380
Fathead Minnow
4.640
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
557.700
Hydration Free Energy
-4.300
Log(D) at pH=7.4
1.840
Log(P)
1.15
Log S
-3.62
Log(Vapor Pressure)
-11.53
Melting Point
237.98
pKa Acid
6.57
pKa Basic
4.92
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 3 0.9549
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 3 0.9029
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.8863
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.8582
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8382
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8201
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7981
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7944
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7734
Malate dehydrogenase P10584 MDH_THETH Thermus thermophilus 3 0.7451
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7417
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7392
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7299
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7254
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7230
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7219
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7208
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7202
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7195
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7166
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7165
Aspartate-semialdehyde dehydrogenase Q51344 DHAS_PSEAE Pseudomonas aeruginosa 3 0.7132
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7124
2'-5'-oligoadenylate synthase 1 P00973 OAS1_HUMAN Homo sapiens 2 0.7038
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7029
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7028
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7025
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7023
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7014
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7013

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