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-/m0/s1
InChIKey MWSTUXWPIZPLKW-DEOSSOPVSA-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]

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
-0.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.390
Plasma Protein Binding
93.6
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
1.070
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
-52.040
Rat (Acute)
2.580
Rat (Chronic Oral)
3.020
Fathead Minnow
5.460
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
534.140
Hydration Free Energy
-4.230
Log(D) at pH=7.4
3.380
Log(P)
4.67
Log S
-7.16
Log(Vapor Pressure)
-9.89
Melting Point
245.3
pKa Acid
7.1
pKa Basic
3.7
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 0.9878
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9878
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9331
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9331
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9275
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9275
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.9103
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.9103
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9026
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9026
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.9022
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.9022
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8879
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8879
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8822
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8822
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8788
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8788
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8591
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8591
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8566
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8566
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8408
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8408
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8358
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8358
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.8309
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.8309
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8268
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8268
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8228
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8228
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8213
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8213
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.8207
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.8207
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8148
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8148
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8124
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8124
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8085
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8085
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8022
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8022
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7969
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7969
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 5 0.7825
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 5 0.7825
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7746
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7746
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7737
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7737
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7692
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7692
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7608
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7608
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7575
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7575
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7565
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7565
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7545
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7545
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7517
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7517
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7493
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7493
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.7408
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.7408
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7400
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7400
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7396
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7396
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7352
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7352
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7274
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7274
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7264
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7264
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7255
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7255
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7238
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7238
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7220
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7220
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7219
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7219
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7177
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7177
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7127
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7127
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7106
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7106
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 4 0.7091
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 4 0.7091
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 4 0.7061
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 4 0.7061
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7056
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7056
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7007
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7007
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7002
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7002

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