Preussiafuran A - Compound Card

Preussiafuran A

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Preussiafuran A

Structure
Zoomed Structure
  • Family: Fungi - Sporormiaceae
  • Kingdom: Fungi, Plantae
  • Class: Coumarin
    • Subclass: Dibenzofuran Derivative
Canonical Smiles OCc1c(C(=O)O)c(C)c2c(c1O)oc1c2c(O)c2c(c1C)COC2
InChI InChI=1S/C18H16O7/c1-6-9-4-24-5-10(9)14(20)13-12-7(2)11(18(22)23)8(3-19)15(21)17(12)25-16(6)13/h19-21H,3-5H2,1-2H3,(H,22,23)
InChIKey NTEMNLFHHMFYJZ-UHFFFAOYSA-N
Formula C18H16O7
HBA 6
HBD 4
MW 344.32
Rotatable Bonds 2
TPSA 120.36
LogP 2.83
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 344.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Enantia chlorantha Annonaceae Plantae 306909
2 Preussia sp. Sporormiaceae Fungi 1715257

Showing of synonyms

  • Talontsi FM, Lamshöft M, et al. (2014). Antiplasmodial and cytotoxic dibenzofurans from Preussia sp. harboured in Enantia chlorantha Oliv.. Fitoterapia,2014, 93, 233-238. [View] [PubMed]
Pubchem: 81689922

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)oc2cc4c(c3)COC4

Level: 0

Mol. Weight: 344.32 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.0
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-5.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.17
Plasma Protein Binding
70.98
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
Non-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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.7
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.67
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.59
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.61
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
1.83
Rat (Acute)
2.21
Rat (Chronic Oral)
3.87
Fathead Minnow
4.02
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
500.25
Hydration Free Energy
-7.45
Log(D) at pH=7.4
-0.05
Log(P)
2.79
Log S
-2.74
Log(Vapor Pressure)
-12.73
Melting Point
261.57
pKa Acid
4.29
pKa Basic
5.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9416
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8359
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8355
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.8251
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8158
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8089
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8014
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.7919
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7894
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7730
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7704
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7677
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7579
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7573
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7529
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7479
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7315
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7303
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7269
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7163
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7096
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7066
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7055
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7044
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7011

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