4'-O-demethylknipholone - Compound Card

4'-O-demethylknipholone

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4'-O-demethylknipholone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles Oc1ccc2c(c1)C(=O)c1c(C2=O)c(c(cc1O)C)c1c(O)cc(c(c1O)C(=O)C)O
InChI InChI=1S/C23H16O8/c1-8-5-13(26)19-20(21(29)11-4-3-10(25)6-12(11)22(19)30)16(8)18-15(28)7-14(27)17(9(2)24)23(18)31/h3-7,25-28,31H,1-2H3
InChIKey ZWQAETRZJQREBW-UHFFFAOYSA-N
Formula C23H16O8
HBA 8
HBD 5
MW 420.37
Rotatable Bonds 2
TPSA 152.36
LogP 3.17
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.09
Exact Mass 420.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine frutescens Asphodelaceae Plantae 210954

Showing of synonyms

  • Bringmann G, Mutanyatta-Comar J, et al. (2008). Joziknipholones A and B: the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens. Chemistry: A European Journal,2008,14(5),1420-429. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4ccccc4

Level: 1

Mol. Weight: 420.37 g/mol

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 420.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 420.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.27
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.130
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.020
Plasma Protein Binding
85.25
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
9.850
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.150
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.020
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.680
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
-28.440
Rat (Acute)
2.540
Rat (Chronic Oral)
3.850
Fathead Minnow
4.460
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
576.050
Hydration Free Energy
-7.080
Log(D) at pH=7.4
3.000
Log(P)
4.5
Log S
-7.29
Log(Vapor Pressure)
-8.87
Melting Point
298.17
pKa Acid
8.51
pKa Basic
5.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9103
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9103
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8687
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8687
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8580
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8580
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8384
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8384
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8348
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8348
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7904
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7904
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7880
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7880
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7849
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7849
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7673
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7673
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7668
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7668
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7657
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7657
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7637
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7637
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7614
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7614
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7406
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7406
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7400
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7400
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7388
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7388
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7335
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7335
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7323
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7323
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7322
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7322
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7277
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7277
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7228
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7228
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7220
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7220
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7188
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7188
Mitogen-activated protein kinase 14 P47811 MK14_MOUSE Mus musculus 4 0.7132
Mitogen-activated protein kinase 14 P47811 MK14_MOUSE Mus musculus 4 0.7132
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7109
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7109
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7100
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7100

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