Roquefortine C - Compound Card

Roquefortine C

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Roquefortine C

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles C=CC([C@@]12C[C@@H]3N([C@@H]1Nc1c2cccc1)C(=O)/C(=C\c1cnc[nH]1)/NC3=O)(C)C
InChI InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+/t17-,20-,22+/m0/s1
InChIKey SPWSUFUPTSJWNG-JJUKSXGLSA-N
Formula C22H23N5O2
HBA 4
HBD 3
MW 389.46
Rotatable Bonds 3
TPSA 90.12
LogP 2.38
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 389.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Penicillium chrysogenum Trichocomaceae Fungi 5076

Showing of synonyms

  • 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]
CPRiL: 83653
Structure

SMILES: [nH]1cncc1C=C(NC2=O)C(=O)N3C2CC4C3Nc(c45)cccc5

Level: 1

Mol. Weight: 389.46 g/mol

Structure

SMILES: O=C1NC(=C)C(=O)N2C1CC3C2Nc(c34)cccc4

Level: 0

Mol. Weight: 389.46 g/mol

Structure

SMILES: c1c[nH]cn1

Level: 0

Mol. Weight: 389.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.42
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.29
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.09
Plasma Protein Binding
76.54
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-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
9.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.34
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.65
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
Safe
T. Pyriformis
-35.42
Rat (Acute)
2.5
Rat (Chronic Oral)
2.25
Fathead Minnow
4.46
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
554.77
Hydration Free Energy
-5.5
Log(D) at pH=7.4
2.7
Log(P)
3.06
Log S
-3.29
Log(Vapor Pressure)
-10.76
Melting Point
277.86
pKa Acid
8.03
pKa Basic
5.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutaminyl-peptide cyclotransferase Q16769 QPCT_HUMAN Homo sapiens 4 0.8864
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8509
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8414
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8245
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8183
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8046
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.8036
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7960
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7928
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.7894
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.7890
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7767
Cyclic GMP-AMP synthase Q8C6L5 CGAS_MOUSE Mus musculus 3 0.7762
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7715
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7706
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7698
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7669
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7667
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7665
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7632
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7627
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7618
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7599
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7586
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7586
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7563
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7548
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7542
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7523
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7501
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7480
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7462
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7447
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7416
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7392
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7377
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7364
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7362
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7330
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7259
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7242
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7226
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7209
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 2 0.7185
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 2 0.7164
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7146
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7139
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 3 0.7126
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7124
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7108
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7099
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7099
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7077
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7074
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7072
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7071
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7070
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7066
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7064
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7046
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7045
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7042
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7040
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7022
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7015
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7014

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