Preussiafuran B - Compound Card

Preussiafuran B

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Preussiafuran B

Structure
Zoomed Structure
  • Family: Fungi - Sporormiaceae
  • Kingdom: Fungi, Plantae
  • Class: Coumarin
    • Subclass: Dibenzofuran Derivative
Canonical Smiles OC(=O)c1c(O)c(O)c2c(c1C)c1c(O)c3COCc3c(c1o2)C
InChI InChI=1S/C17H14O7/c1-5-7-3-23-4-8(7)12(18)11-9-6(2)10(17(21)22)13(19)14(20)16(9)24-15(5)11/h18-20H,3-4H2,1-2H3,(H,21,22)
InChIKey AEAOLRJWRKFEIC-UHFFFAOYSA-N
Formula C17H14O7
HBA 6
HBD 4
MW 330.29
Rotatable Bonds 1
TPSA 120.36
LogP 3.05
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 330.07
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: 81689923

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)oc2cc4c(c3)COC4

Level: 0

Mol. Weight: 330.29 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-4.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
66.39
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
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
6.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.02
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.77
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.42
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
3.65
Rat (Acute)
2.14
Rat (Chronic Oral)
3.83
Fathead Minnow
3.93
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
487.43
Hydration Free Energy
-6.68
Log(D) at pH=7.4
0.82
Log(P)
3.37
Log S
-2.72
Log(Vapor Pressure)
-12.88
Melting Point
296.69
pKa Acid
3.91
pKa Basic
5.81
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 0.9283
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8827
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8478
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8431
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8296
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.8167
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8150
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8143
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8136
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8077
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.8057
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7931
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7925
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7909
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7866
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7850
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7814
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7787
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7675
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7643
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7560
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7503
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7479
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7457
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7445
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7444
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7407
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7400
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7371
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7318
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7304
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7267
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7247
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 4 0.7220
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7189
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7145
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7138
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7129
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7123
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7085
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 5 0.7070
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7059
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7052
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7046
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7015

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