Isoknipholone - Compound Card

Isoknipholone

Select a section from the left sidebar

Isoknipholone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1c(c(O)cc(c1C(=O)C)O)c1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)O)O
InChI InChI=1S/C24H18O8/c1-9-7-13(27)19-21(22(30)11-5-4-6-12(26)18(11)23(19)31)16(9)20-15(29)8-14(28)17(10(2)25)24(20)32-3/h4-8,26-29H,1-3H3
InChIKey VNABVYKJDAAAMB-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

Showing of synonyms

  • 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]
  • 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]
  • 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]
Pubchem: 12178518
Nmrshiftdb2: 60063497

No compound-protein relationship available.

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-plasmodial

Absorption

Caco-2 (logPapp)
-5.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
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)
1.150
Plasma Protein Binding
84.13
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
8.890
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.260
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
6.100
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
-54.430
Rat (Acute)
2.530
Rat (Chronic Oral)
3.500
Fathead Minnow
4.970
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
555.120
Hydration Free Energy
-4.500
Log(D) at pH=7.4
3.070
Log(P)
4.93
Log S
-7.49
Log(Vapor Pressure)
-9.0
Melting Point
254.42
pKa Acid
8.64
pKa Basic
3.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.9105
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.9105
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8853
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8853
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8597
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8597
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8573
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8573
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8096
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8096
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8070
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8070
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8010
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8010
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7899
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7899
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7872
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7872
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7772
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7772
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7742
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7742
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7657
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7657
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7646
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7646
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7603
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7603
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7603
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7603
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7574
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7574
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7479
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7479
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7420
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7420
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7397
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7397
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7368
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7368
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7363
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7363
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7351
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7351
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7328
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7328
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7297
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7297
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7293
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7293
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7268
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7268
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7235
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7235
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7223
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7223
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7207
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7207
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7203
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7203
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7157
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7157
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7135
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7135
Tyrosyl-DNA phosphodiesterase 2 Q9JJX7 TYDP2_MOUSE Mus musculus 3 0.7124
Tyrosyl-DNA phosphodiesterase 2 Q9JJX7 TYDP2_MOUSE Mus musculus 3 0.7124
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7110
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7110
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7076
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7076
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7053
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7053
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7047
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7047
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7038
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7038
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7032
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7032
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7024
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7024
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7020
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7020
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7020
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7020
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7007
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7007
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7002
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7002

Download SDF