10-acetonylknipholone cyclooxanthrone - Compound Card

10-acetonylknipholone cyclooxanthrone

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10-acetonylknipholone cyclooxanthrone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Phenylanthraquinones/Anthrone
Canonical Smiles COc1cc2OC3(CC(=O)C)c4c(c2c(c1C(=O)C)O)c(C)cc(c4C(=O)c1c3cccc1O)O
InChI InChI=1S/C27H22O8/c1-11-8-16(31)22-24-19(11)23-18(9-17(34-4)20(13(3)29)25(23)32)35-27(24,10-12(2)28)14-6-5-7-15(30)21(14)26(22)33/h5-9,30-32H,10H2,1-4H3
InChIKey RJPFLCZZRWQDMM-UHFFFAOYSA-N
Formula C27H22O8
HBA 8
HBD 3
MW 474.47
Rotatable Bonds 4
TPSA 130.36
LogP 4.15
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 474.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Kniphofia foliosa Asphodelaceae Plantae 214838

Showing of synonyms

  • Induli M, Gebru M, et al. (2013). Antiplasmodial Quinones from the Rhizomes of Kniphofia foliosa. Natural Product Communications,2013,8(9),1261-1264. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 474.47 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.35
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.330
Plasma Protein Binding
76.2
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
9.040
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.580
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.850
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.510
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-291.400
Rat (Acute)
2.670
Rat (Chronic Oral)
3.170
Fathead Minnow
6.150
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
561.350
Hydration Free Energy
-3.040
Log(D) at pH=7.4
2.970
Log(P)
3.93
Log S
-6.84
Log(Vapor Pressure)
-10.19
Melting Point
229.07
pKa Acid
6.79
pKa Basic
3.82
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 0.9839
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9839
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9725
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9725
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9025
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9025
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8682
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8682
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8481
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8481
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8308
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8308
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8215
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.8215
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8199
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8199
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.8165
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.8165
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8141
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8141
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8136
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8136
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8096
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8096
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8082
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8082
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8078
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8078
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8034
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8034
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8008
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8008
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7994
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7994
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7941
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7941
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7930
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7930
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7925
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7925
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7925
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7925
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7892
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7892
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7851
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7851
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7805
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7805
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7779
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7779
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7751
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7751
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7745
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7745
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 5 0.7734
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 5 0.7734
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.7730
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.7730
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7702
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 4 0.7702
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7599
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7599
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 4 0.7583
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 4 0.7583
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7575
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7575
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7557
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7557
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7546
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7546
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7534
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7534
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7487
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7487
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7485
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7485
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7476
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7476
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7412
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7412
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.7396
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 3 0.7396
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7390
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7390
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7354
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7354
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7350
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7350
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7299
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7299
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7273
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7273
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7256
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7256
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7109
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7109
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7083
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7083
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7070
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7070
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7068
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7068
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7068
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7068
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7061
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7061
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 4 0.7058
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 4 0.7058
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7043
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7043

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