Aspergillus diketopiperazine 6a - Compound Card

Aspergillus diketopiperazine 6a

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Aspergillus diketopiperazine 6a

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Diketopiperazine
Canonical Smiles O=C1N[C@@H](Cc2cn(c3c2cccc3)C(=O)OC(C)(C)C)C(=O)N2[C@H]1CCC2
InChI InChI=1S/C21H25N3O4/c1-21(2,3)28-20(27)24-12-13(14-7-4-5-8-16(14)24)11-15-19(26)23-10-6-9-17(23)18(25)22-15/h4-5,7-8,12,15,17H,6,9-11H2,1-3H3,(H,22,25)/t15-,17-/m0/s1
InChIKey YMBWWWKPLURITN-RDJZCZTQSA-N
Formula C21H25N3O4
HBA 5
HBD 1
MW 383.45
Rotatable Bonds 2
TPSA 80.64
LogP 2.46
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 383.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus fumigatus Trichocomaceae Fungi 746128

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]
Pubchem: 122184710
Nmrshiftdb2: 70049674

No compound-protein relationship available.

Structure

SMILES: C1CCN(C12)C(=O)C(NC2=O)Cc3c[nH]c(c34)cccc4

Level: 1

Mol. Weight: 383.45 g/mol

Structure

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

Level: 0

Mol. Weight: 383.45 g/mol

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 383.45 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.24
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.66
Plasma Protein Binding
73.09
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.22
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.39
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.32
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.41
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
-12.78
Rat (Acute)
2.68
Rat (Chronic Oral)
2.25
Fathead Minnow
4.14
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
448.77
Hydration Free Energy
-7.7
Log(D) at pH=7.4
2.51
Log(P)
2.66
Log S
-3.47
Log(Vapor Pressure)
-7.96
Melting Point
184.94
pKa Acid
7.87
pKa Basic
5.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9161
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9161
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8892
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8892
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8415
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8415
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7884
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7884
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7867
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7867
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7832
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7832
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7813
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7813
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7769
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7769
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7693
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7693
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7557
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7557
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7524
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7524
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7369
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7369
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7318
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7318
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7224
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7224
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7166
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7166
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7104
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7104
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7093
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7093
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7060
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7060
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7014
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7014
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7006
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7006

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