6',8-O-dimethylknipholone - Compound Card

6',8-O-dimethylknipholone

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6',8-O-dimethylknipholone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(OC)c(c(c1c1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)OC)O)O)C(=O)C
InChI InChI=1S/C26H22O8/c1-11-9-14(28)21-23(24(29)13-7-6-8-15(32-3)20(13)26(21)31)18(11)22-17(34-5)10-16(33-4)19(12(2)27)25(22)30/h6-10,28,30H,1-5H3
InChIKey FWLOWRJYYJIUHJ-UHFFFAOYSA-N
Formula C26H22O8
HBA 8
HBD 2
MW 462.45
Rotatable Bonds 5
TPSA 119.36
LogP 4.08
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 462.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine frutescens Asphodelaceae Plantae 210954

Showing of synonyms

  • Abdissa N, Heydenreich M, et al. (2014). A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters,2014,9,67-73. [View] [PubMed]
Pubchem: 102138459

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 462.45 g/mol

Structure

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

Level: 0

Mol. Weight: 462.45 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.45 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.800
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.290
Plasma Protein Binding
79.84
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.180
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.160
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.960
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.200
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
-176.320
Rat (Acute)
2.630
Rat (Chronic Oral)
3.290
Fathead Minnow
5.790
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
546.140
Hydration Free Energy
-3.000
Log(D) at pH=7.4
3.320
Log(P)
4.46
Log S
-8.63
Log(Vapor Pressure)
-9.21
Melting Point
201.63
pKa Acid
6.51
pKa Basic
3.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9267
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9267
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9074
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9074
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8924
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8924
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8910
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8910
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8641
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8641
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8571
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8571
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8387
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8387
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8241
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8241
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8181
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8181
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8053
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8053
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7977
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7977
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7943
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7943
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7898
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7898
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7861
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7861
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7815
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7815
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7777
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7777
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7764
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7764
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7755
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7755
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7749
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7749
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7744
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7744
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7693
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7693
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7689
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7689
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7664
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7664
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7580
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7580
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7563
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7563
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.7560
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.7560
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7474
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7474
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7464
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7464
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7419
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7419
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7403
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7403
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7395
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7395
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7378
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7378
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7369
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7369
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7343
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7343
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 4 0.7324
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 4 0.7324
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7312
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7312
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7292
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7292
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7291
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7291
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.7281
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.7281
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7278
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7278
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7268
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7268
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7250
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7250
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7241
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7241
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7205
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7205
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7187
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7187
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7180
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7180
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7167
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7167
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7166
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7166
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.7160
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 3 0.7160
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7135
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7135
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7079
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7079
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7022
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7022
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7005
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7005

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