Knipholone cyclooxanthrone - Compound Card

Knipholone cyclooxanthrone

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Knipholone cyclooxanthrone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles COc1cc2O[C@H]3c4c(c2c(c1C(=O)C)O)c(C)cc(c4C(=O)c1c3cccc1O)O
InChI InChI=1S/C24H18O7/c1-9-7-13(27)19-21-16(9)20-15(8-14(30-3)17(10(2)25)22(20)28)31-24(21)11-5-4-6-12(26)18(11)23(19)29/h4-8,24,26-28H,1-3H3/t24-/m1/s1
InChIKey MWSTUXWPIZPLKW-XMMPIXPASA-N
Formula C24H18O7
HBA 7
HBD 3
MW 418.4
Rotatable Bonds 2
TPSA 113.29
LogP 4.02
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 418.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Kniphofia foliosa Asphodelaceae Plantae 214838

Showing of synonyms

  • Abdissa N, Induli M, et al. (2013). Knipholone cyclooxanthrone and an anthraquinone dimer with antiplasmodial activities from the roots of Kniphofia foliosa. Phytochemistry Letters,2013,6(2),241-245. [View] [PubMed]
Pubchem: 163061003

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)OC4c2c(ccc3)C(=O)c5c4cccc5

Level: 0

Mol. Weight: 418.4 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.18
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.390
Plasma Protein Binding
93.54
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.990
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.040
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.980
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.000
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
-52.220
Rat (Acute)
2.580
Rat (Chronic Oral)
3.010
Fathead Minnow
5.450
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
534.740
Hydration Free Energy
-4.250
Log(D) at pH=7.4
3.410
Log(P)
4.64
Log S
-7.14
Log(Vapor Pressure)
-9.87
Melting Point
242.64
pKa Acid
7.11
pKa Basic
3.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9866
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9866
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9592
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9592
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.9330
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.9330
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9231
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9231
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.9215
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.9215
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9210
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9210
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.9112
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.9112
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9046
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9046
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.8939
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.8939
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8592
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8592
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8589
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8589
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8489
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8489
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8466
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8466
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8456
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8456
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.8338
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.8338
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8266
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8266
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8246
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8246
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8082
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8082
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8079
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8079
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8063
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8063
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8061
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8061
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7810
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7810
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7790
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7790
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7727
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7727
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7687
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7687
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7636
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7636
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7574
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7574
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7466
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7466
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7458
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7458
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7441
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7441
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7436
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7436
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7426
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7426
Protein mono-ADP-ribosyltransferase PARP14 Q460N5 PAR14_HUMAN Homo sapiens 3 0.7410
Protein mono-ADP-ribosyltransferase PARP14 Q460N5 PAR14_HUMAN Homo sapiens 3 0.7410
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7380
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7380
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7272
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7272
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7246
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7246
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7230
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7230
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7227
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7227
Bromodomain-containing protein 9 Q9H8M2 BRD9_HUMAN Homo sapiens 3 0.7224
Bromodomain-containing protein 9 Q9H8M2 BRD9_HUMAN Homo sapiens 3 0.7224
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 4 0.7219
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 4 0.7219
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7197
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7197
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7159
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7159
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7158
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7158
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 5 0.7152
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 5 0.7152
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 4 0.7136
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 4 0.7136
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7132
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7132
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7131
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7131
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7127
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7127
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7098
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7098
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7095
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7095
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7094
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7094
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7071
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7071
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7049
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7049
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7029
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7029
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7012
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7012

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