Aspergillus diketopiperazine 7 - Compound Card

Aspergillus diketopiperazine 7

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Aspergillus diketopiperazine 7

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Fungi, Plantae
  • Class: Alkaloid
    • Subclass: Diketopiperazine
Canonical Smiles O=C1N[C@@H](Cc2ccccc2)C(=O)N2[C@H]1CCC2
InChI InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12-/m0/s1
InChIKey QZBUWPVZSXDWSB-RYUDHWBXSA-N
Formula C14H16N2O2
HBA 2
HBD 1
MW 244.29
Rotatable Bonds 2
TPSA 49.41
LogP 0.72
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.43
Exact Mass 244.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus fumigatus Trichocomaceae Fungi 746128
2 Nigrospora sphaerica Trichosphaeriaceae Fungi 114231
3 Dendrothyrium variisporum Montagnulaceae Fungi 1985348
4 Eucalyptus citriodora Myrtaceae Plantae 34329

Showing of synonyms

  • El-Gendy BEDM, Rateb ME (2015). Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification. Bioorganic and Medicinal Chemistry Letters,2015,25(16),3125-3128. [View] [PubMed]
  • Teponno RB, Noumeur SR, et al. (2017). Furanones and anthranilic acid derivatives from the endophytic fungus Dendrothyrium variisporum. Molecules 2017, 22(10), 1674. [View] [PubMed]
  • Metwaly AM, Kadry HA, et al. (2014). Nigrosphaerin A a new isochromene derivative from the endophytic fungus Nigrospora sphaerica. Phytochemistry Letters,2014,7,1-5. [View]
  • Al-Sayed E, El-Naga R.N. (2015). Protective role of ellagitannins from Eucalyptus citriodora against ethanol-induced gastriculcerinrats: Impact on oxidative stress, inflammation and calcitonin-generelated peptide.. Phytomedicine : international journal of phytotherapy and phytopharmacology,2015, 22(1), 5-15. [View] [PubMed]
Pubchem: 443440
Kegg Ligand: C11847
Chebi: 69440
Nmrshiftdb2: 20124
Metabolights: MTBLC69440
Bindingdb: 163710
CPRiL: 88756
Structure

SMILES: c1ccccc1CC(NC2=O)C(=O)N(C23)CCC3

Level: 1

Mol. Weight: 244.29 g/mol

Structure

SMILES: C1CCN(C12)C(=O)CNC2=O

Level: 0

Mol. Weight: 244.29 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 244.29 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.18
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.46
Plasma Protein Binding
52.88
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
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.06
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.73
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.38
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.74
Micronucleos
Toxic
NR-AhR
Safe
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
0.49
Rat (Acute)
2.25
Rat (Chronic Oral)
2.2
Fathead Minnow
3.83
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
381.5
Hydration Free Energy
-13.91
Log(D) at pH=7.4
1.1
Log(P)
0.91
Log S
-1.98
Log(Vapor Pressure)
-7.28
Melting Point
166.32
pKa Acid
8.89
pKa Basic
5.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.9778
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.9778
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9533
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9533
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.9400
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.9400
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9355
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9355
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.9215
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.9215
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8934
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8934
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8799
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8799
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8733
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8733
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8693
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8693
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8689
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8689
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8552
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8552
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8432
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8432
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8431
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8431
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8427
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8427
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8307
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8307
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8099
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8099
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.8097
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.8097
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8063
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8063
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7997
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7997
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7978
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7978
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7962
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7962
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7903
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7903
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7897
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7897
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7878
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7878
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7861
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7861
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7858
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7858
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7747
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7747
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7743
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7743
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.7710
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.7710
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7702
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7702
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7701
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7701
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7681
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7681
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7639
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7639
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7609
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7609
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7601
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7601
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7601
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7601
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7585
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7585
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7574
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7574
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7574
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7574
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7542
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7542
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7539
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7539
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7535
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7535
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7514
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7514
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7475
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7475
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7426
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7426
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7417
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7417
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7381
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7381
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7355
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7355
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7335
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7335
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7333
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7333
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7333
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7333
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7308
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7308
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7302
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7302
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7295
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7295
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7277
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7277
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7273
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7273
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7248
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7248
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7242
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7242
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7228
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7228
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7204
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7204
Penicillin V acylase P12256 PAC_LYSSH Lysinibacillus sphaericus 3 0.7196
Penicillin V acylase P12256 PAC_LYSSH Lysinibacillus sphaericus 3 0.7196
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7191
Glucocorticoid receptor P04150 GCR_HUMAN Homo sapiens 3 0.7191
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7188
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7188
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 2 0.7180
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 2 0.7180
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7173
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7173
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7167
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7167
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 2 0.7135
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 2 0.7135
Glutaminyl-peptide cyclotransferase Q16769 QPCT_HUMAN Homo sapiens 3 0.7127
Glutaminyl-peptide cyclotransferase Q16769 QPCT_HUMAN Homo sapiens 3 0.7127
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7122
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7122
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7120
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7120
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 2 0.7112
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 2 0.7112
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7087
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7087
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7058
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7058
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7048
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7048
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7046
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7046
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7031
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7031
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7030
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7030
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7026
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7026
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7016
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7016
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7004
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7004

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