Aspergillus diketopiperazine 4a - Compound Card

Aspergillus diketopiperazine 4a

Select a section from the left sidebar

Aspergillus diketopiperazine 4a

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Diketopiperazine
Canonical Smiles COc1ccc2c(c1)n(C(=O)OC(C)(C)C)c1c2C[C@@H]2N([C@H]1C=C(C)C)C(=O)[C@H]1N(C2=O)CCC1
InChI InChI=1S/C27H33N3O5/c1-15(2)12-21-23-18(14-22-24(31)28-11-7-8-19(28)25(32)29(21)22)17-10-9-16(34-6)13-20(17)30(23)26(33)35-27(3,4)5/h9-10,12-13,19,21-22H,7-8,11,14H2,1-6H3/t19-,21-,22-/m0/s1
InChIKey UVFKCBGMNYWBCA-BVSLBCMMSA-N
Formula C27H33N3O5
HBA 6
HBD 0
MW 479.58
Rotatable Bonds 2
TPSA 81.08
LogP 4.2
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 479.24
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: 122184708
Nmrshiftdb2: 70049675

No compound-protein relationship available.

Structure

SMILES: c1cccc2[nH]c(c3c12)CN4C(C3)C(=O)N5C(C4=O)CCC5

Level: 0

Mol. Weight: 479.58 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.500
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.150
Plasma Protein Binding
89.13
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
7.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.450
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.500
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-402.520
Rat (Acute)
2.670
Rat (Chronic Oral)
2.200
Fathead Minnow
5.520
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
519.780
Hydration Free Energy
-2.870
Log(D) at pH=7.4
3.100
Log(P)
4.05
Log S
-4.38
Log(Vapor Pressure)
-8.81
Melting Point
221.9
pKa Acid
7.81
pKa Basic
4.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9198
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9198
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8841
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8841
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8650
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8650
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.8032
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.8032
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7471
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7471
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7452
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7452
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7413
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7413
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7387
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7387
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7326
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7326
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7206
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7206
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7070
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7070
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7049
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7049
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7032
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7032

Download SDF