Knipholone - Compound Card

Knipholone

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Knipholone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(O)c(c(c1C(=O)C)O)c1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)O)O
InChI InChI=1S/C24H18O8/c1-9-7-13(27)20-21(22(29)11-5-4-6-12(26)18(11)24(20)31)16(9)19-14(28)8-15(32-3)17(10(2)25)23(19)30/h4-8,26-28,30H,1-3H3
InChIKey DUENHQWYLVQDQK-UHFFFAOYSA-N
Formula C24H18O8
HBA 8
HBD 4
MW 434.4
Rotatable Bonds 3
TPSA 141.36
LogP 3.47
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 434.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine frutescens Asphodelaceae Plantae 210954
2 Kniphofia foliosa Asphodelaceae Plantae 214838
3 Kniphofia foliosa Asphodelaceae Plantae 214838
4 Bulbine frutescens Asphodelaceae Plantae 210954
5 Senna didymobotrya Leguminosae/Fabaceae Plantae 72401
6 Kniphofia species Liliaceae Plantae 49723
7 Kniphofia foliosa Asphodelaceae Plantae 214838
8 Kniphofia species Liliaceae Plantae 49723
9 Kniphofia foliosa Liliaceae Plantae 214838
10 Kniphofia foliosa Asphodelaceae Plantae 214838
11 Kniphofia foliosa Asphodelaceae Plantae 214838

Showing of synonyms

  • Yenesew A, Wondimu A, et al. (1988). A comparative study of anthraquinones in rhizomes of Kniphofia species.. Biochemical systematics and ecology,1988,16(2),157-159. [View] [PubMed]
  • 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]
  • Yenesew A, Dagne E, et al. (1994). An anthrone, an anthraquinone and two oxanthrones from Kniphofia foliosa. Phytochemistry,1994,37(2),525-528. [View] [PubMed]
  • Berhanu E, Fetene M, et al. (1986). Anthraquinones as taxonomic markers in Ethiopian Kniphofia species.. Phytochemistry,1986,25(4),847-850. [View] [PubMed]
  • Wube AA, Bucar F, et al. (2005). Antimalarial compounds from Kniphofia foliosa roots.. Phytother Research,2005,19(6),472-476. [View] [PubMed]
  • 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]
  • Alemayehu G, Hailu A, et al. (1996). Bianthraquinones from Senna didymobotrya. Phytochemistry,1996,42(5),1423-1425. [View] [PubMed]
  • Feilcke R, Arnouk G, et al. (2019). Biological activity and stability analyses of knipholone anthrone, a phenyl anthraquinone derivative isolated from Kniphofia foliosa Hochst.. Journal of Pharmaceutical and Biomedical Analysis,2019,174,277-285.. [View] [PubMed]
  • Bringmann G, Mutanyatta-Comar J, et al. (2008). Joziknipholones A and B: the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens. Chemistry: A European Journal,2008,14(5),1420-429. [View] [PubMed]
  • Dagne E, Yenesew A. (1993). Knipholone anthrone from Kniphofia foliosa.. Phytochemistry,1993,34(5),1440-1441. [View] [PubMed]
  • Dagne E, Steglich W. (1984). Knipholone: a unique anthraquinone derivative from Kniphofia foliosa.. Phytochemistry,1984,23(8),1729-1731. [View] [PubMed]
Pubchem: 442753
Kegg Ligand: C10365
Chebi: 6141
Nmrshiftdb2: 60060454
Metabolights: MTBLC6141
CPRiL: 75095
Structure

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

Level: 1

Mol. Weight: 434.4 g/mol

Structure

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

Level: 0

Mol. Weight: 434.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.4 g/mol

Anti-hiv
Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.83
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.940
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.170
Plasma Protein Binding
83.92
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.970
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.510
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.130
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.860
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
-55.370
Rat (Acute)
2.510
Rat (Chronic Oral)
3.650
Fathead Minnow
4.940
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
561.390
Hydration Free Energy
-4.610
Log(D) at pH=7.4
2.880
Log(P)
4.83
Log S
-7.85
Log(Vapor Pressure)
-9.09
Melting Point
242.98
pKa Acid
7.05
pKa Basic
4.32
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 0.9186
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9186
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.9031
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.9031
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8709
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8709
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8500
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8500
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8145
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8145
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.8119
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.8119
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8029
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8029
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7926
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7926
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7840
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.7840
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7681
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7681
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7675
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7675
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7567
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7567
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7517
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7517
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7509
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7509
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7453
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7453
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7453
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7453
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7440
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7440
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7436
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7436
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7365
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7365
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7308
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7308
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7296
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7296
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7286
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7286
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7259
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7259
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7251
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7251
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7245
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7245
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.7235
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.7235
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7228
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7228
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7214
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7214
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7181
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7181
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7181
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7181
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7169
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7169
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7163
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7163
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7160
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7160
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7114
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7114
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7037
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7037
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7020
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7020

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