6,6′-dinor-bipenicilisorin - Compound Card

6,6′-dinor-bipenicilisorin

Select a section from the left sidebar

6,6′-dinor-bipenicilisorin

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Coumarin
    • Subclass: Dimeric Isocoumarin
Canonical Smiles COC(=O)c1cc2cc(O)c(c(c2c(=O)o1)O)c1c(O)cc2c(c1O)c(=O)oc(c2)C(=O)OC
InChI InChI=1S/C22H14O12/c1-31-19(27)11-5-7-3-9(23)15(17(25)13(7)21(29)33-11)16-10(24)4-8-6-12(20(28)32-2)34-22(30)14(8)18(16)26/h3-6,23-26H,1-2H3
InChIKey BHEQGSUFUDMFEA-UHFFFAOYSA-N
Formula C22H14O12
HBA 12
HBD 4
MW 470.34
Rotatable Bonds 3
TPSA 193.94
LogP 1.96
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.09
Exact Mass 470.05
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus versicolor Trichocomaceae Fungi 46472

Showing of synonyms

  • Ebada S, El-Neketi M, et al. (2018). Cytotoxic secondary metabolites from the endophytic fungus Aspergillus versicolor KU258497. Phytochemistry Letters,2018,24,88–93. [View]
Pubchem: 23958176
Nmrshiftdb2: 70097023

No compound-protein relationship available.

Structure

SMILES: O=c1occc(c12)ccc(c2)-c(c3)ccc(c34)ccoc4=O

Level: 1

Mol. Weight: 470.34 g/mol

Structure

SMILES: c1cccc(c12)ccoc2=O

Level: 0

Mol. Weight: 470.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.37
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.980
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.100
Plasma Protein Binding
73.89
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
6.400
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.010
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.030
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.610
Micronucleos
Toxic
NR-AhR
Toxic
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
-159.980
Rat (Acute)
2.570
Rat (Chronic Oral)
3.440
Fathead Minnow
4.780
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
609.460
Hydration Free Energy
-3.620
Log(D) at pH=7.4
3.290
Log(P)
3.47
Log S
-6.33
Log(Vapor Pressure)
-9.42
Melting Point
277.55
pKa Acid
8.77
pKa Basic
4.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9087
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8920
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8716
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8569
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8415
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8330
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8257
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7797
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7764
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7738
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 3 0.7714
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.7673
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 3 0.7631
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7617
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7612
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7502
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7474
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7411
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7329
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7327
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7271
Farnesyl pyrophosphate synthase Q4QBL1 Q4QBL1_LEIMA Leishmania major 3 0.7206
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.7205
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7198
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7172
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7071
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7067
Prothrombin P00734 THRB_HUMAN Homo sapiens 4 0.7040
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7036

Download SDF