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Roquefortine C
- 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
Roquefortine C
Roquefortine
Roquefortin
UNII-4VW6U94XFK
HSDB 7246
(1S,4E,7S,9R)-4-(1H-imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
ROQUEFORTINE [HSDB]
BRN 1231991
(-)-ROQUEFORTINE C
DTXSID20891816
NSC-292134
2H-Pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propenyl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-4-ylmethylene)-
2H-PYRAZINO(1',2':1,5)PYRROLO(2,3-B)INDOLE-1,4(3H,5AH)-DIONE, 10B-(1,1-DIMETHYL-2-PROPEN-1-YL)-6,10B,11,11A-TETRAHYDRO-3-(1H-IMIDAZOL-5-YLMETHYLENE)-, (3E,5AS,10BR,11AS)-
2H-PYRAZINO(1',2':1,5)PYRROLO(2,3-B)INDOLE-1,4(3H,5AH)-DIONE, 10B-(1,1-DIMETHYL-2-PROPENYL)-6,10B,11,11A-TETRAHYDRO-3-(1H-IMIDAZOL-4-YLMETHYLENE)-, (3E,5AS,10BR,11AS)-
(1S,4E,7S,9R)-4-(1H-imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo(7.7.0.02,7.010,15)hexadeca-10,12,14-triene-3,6-dione
(4Z)-6-hydroxy-4-(1H-imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo(7.7.0.02,7.010,15)hexadeca-5,10,12,14-tetraen-3-one
(4Z)-6-hydroxy-4-(1H-imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-5,10,12,14-tetraen-3-one
2H-Pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propenyl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-4-ylmethylene)-, (3E,5aS,10bR,11aS)-
DTXCID201031054
2H-Pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4-(3H,5ah)-dione, 6,10b,11,11a-tetrahydro-10b-(1,1-dimethyl-2-propenyl)-3-(1H-imidazol-4-ylmethylene)-
2HPyrazino(1',2':1,5)pyrrolo(2,3b)indole1,4(3H,5aH)dione, 10b(1,1dimethyl2propenyl)6,10b,11,11atetrahydro3(1Himidazol4ylmethylene)
2HPyrazino(1',2':1,5)pyrrolo(2,3b)indole1,4(3H,5aH)dione, 6,10b,11,11atetrahydro10b(1,1dimethyl2propenyl)3(1Himidazol4ylmethylene)
6,10b,11,11a-tetrahydro-10b-(1,1-dimethyl-2-propenyl)-3-(1H-imidazol-4-ylmethylene)-2H-Pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4-(3H,5ah)-dione
Spwsufuptsjwng-sxgwcwsvsa-n
58735-64-1
4VW6U94XFK
Isoroquefortine C
(1S,4Z,7S,9R)-4-(1H-Imidazol-5-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione
NSC 292134
CHEMBL517788
CHEBI:183713
HY-N6748
AKOS040740902
NCGC00489127-01
BR162745
CS-0099780
NS00018320
G91402
68628-81-9
- 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:
21608802
Cas:
58735-64-1
Gnps:
CCMSLIB00004707466
Zinc:
ZINC000014687876
Chebi:
183713
Nmrshiftdb2:
70130328
Chembl:
CHEMBL517788
Comptox:
DTXSID20891816
CPRiL:
83653
SMILES: [nH]1cncc1C=C(NC2=O)C(=O)N3C2CC4C3Nc(c45)cccc5
Level: 1
Mol. Weight: 389.46 g/mol
SMILES: O=C1NC(=C)C(=O)N2C1CC3C2Nc(c34)cccc4
Level: 0
Mol. Weight: 389.46 g/mol
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 |