8,8′-dihydroxy-1,1′,3,3′-tetramethoxy-6,6′-dimethyl-10,10′-bianthrone - Compound Card

8,8′-dihydroxy-1,1′,3,3′-tetramethoxy-6,6′-dimethyl-10,10′-bianthrone

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8,8′-dihydroxy-1,1′,3,3′-tetramethoxy-6,6′-dimethyl-10,10′-bianthrone

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Bianthrone
Canonical Smiles COc1cc(OC)c2c(c1)C(C1c3cc(C)cc(c3C(=O)c3c1cc(OC)cc3OC)O)c1c(C2=O)c(O)cc(c1)C
InChI InChI=1S/C34H30O8/c1-15-7-19-27(21-11-17(39-3)13-25(41-5)31(21)33(37)29(19)23(35)9-15)28-20-8-16(2)10-24(36)30(20)34(38)32-22(28)12-18(40-4)14-26(32)42-6/h7-14,27-28,35-36H,1-6H3
InChIKey LIZAXDZGERGFKW-UHFFFAOYSA-N
Formula C34H30O8
HBA 8
HBD 2
MW 566.61
Rotatable Bonds 5
TPSA 111.52
LogP 5.8
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 566.19
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus wentii Trichocomaceae Fungi 5066

Showing of synonyms

  • Form I.C, Bonus M, et al. (2019). Xanthone, benzophenone and bianthrone derivatives from the hypersaline lake-derived fungus Aspergillus wentii. Bioorg Med Chem,2019,27(20),115005. [View] [PubMed]
Pubchem: 337815

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C(c(c23)cccc3)C(c(c45)cccc5)c6c(C4=O)cccc6

Level: 1

Mol. Weight: 566.61 g/mol

Structure

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 566.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.15
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
6.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.470
Plasma Protein Binding
70.72
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
6.660
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.220
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.280
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.780
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
Toxic
T. Pyriformis
-13565.380
Rat (Acute)
2.800
Rat (Chronic Oral)
3.000
Fathead Minnow
37.910
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
465.790
Hydration Free Energy
-2.910
Log(D) at pH=7.4
4.800
Log(P)
7.41
Log S
-7.24
Log(Vapor Pressure)
-15.03
Melting Point
246.32
pKa Acid
7.64
pKa Basic
1.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9222
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8853
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8640
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8237
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7893
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7868
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7655
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7535
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7393
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7353
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7335
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7259
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7159
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7133
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7129
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7054
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7042
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7025
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7000

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