ANPDB

Select a section from the left sidebar

Knipholone cyclooxanthrone

Family: Plantae - Asphodelaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthrone

Canonical Smiles	COc1cc2OC3c4c(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
InChIKey	MWSTUXWPIZPLKW-UHFFFAOYSA-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
2	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]
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: 163061002

No compound-protein relationship available.

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: 80.66
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: 1.110
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: 5.990
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: -51.330
Rat (Acute): 2.570
Rat (Chronic Oral): 3.010
Fathead Minnow: 5.490
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: 533.210
Hydration Free Energy: -4.250
Log(D) at pH=7.4: 3.400
Log(P): 4.68
Log S: -7.14
Log(Vapor Pressure): -9.78
Melting Point: 240.94
pKa Acid: 7.09
pKa Basic: 3.75

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

Download SDF