Aspergillus diketopiperazine 5a - Compound Card

Aspergillus diketopiperazine 5a

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Aspergillus diketopiperazine 5a

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Diketopiperazine
Canonical Smiles CC(=CCc1n(C(=O)OC(C)(C)C)c2c(c1C[C@H]1C(=O)N3CCC[C@H]3C(=O)N1C(=O)OC(C)(C)C)cccc2)C
InChI InChI=1S/C31H41N3O6/c1-19(2)15-16-23-21(20-12-9-10-13-22(20)33(23)28(37)39-30(3,4)5)18-25-26(35)32-17-11-14-24(32)27(36)34(25)29(38)40-31(6,7)8/h9-10,12-13,15,24-25H,11,14,16-18H2,1-8H3/t24-,25-/m0/s1
InChIKey LCXZJWZQHMZTRX-DQEYMECFSA-N
Formula C31H41N3O6
HBA 7
HBD 0
MW 551.68
Rotatable Bonds 4
TPSA 98.15
LogP 5.61
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 551.3
Number of Lipinski Rule Violations 2
# 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: 122184709
Nmrshiftdb2: 70049673

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 551.68 g/mol

Structure

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

Level: 0

Mol. Weight: 551.68 g/mol

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 551.68 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.39
Plasma Protein Binding
95.95
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
4.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.37
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.57
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.08
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2196.73
Rat (Acute)
2.71
Rat (Chronic Oral)
2.5
Fathead Minnow
12.14
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
453.11
Hydration Free Energy
-2.79
Log(D) at pH=7.4
4.24
Log(P)
6.52
Log S
-5.22
Log(Vapor Pressure)
-7.83
Melting Point
176.14
pKa Acid
7.85
pKa Basic
5.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7486
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7486
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7009
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7009

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