Knipholone anthrone - Compound Card

Knipholone anthrone

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Knipholone anthrone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthrone
Canonical Smiles COc1cc(O)c(c(c1C(=O)C)O)c1c(C)cc(c2c1Cc1cccc(c1C2=O)O)O
InChI InChI=1S/C24H20O7/c1-10-7-15(27)21-13(8-12-5-4-6-14(26)20(12)24(21)30)18(10)22-16(28)9-17(31-3)19(11(2)25)23(22)29/h4-7,9,26-29H,8H2,1-3H3
InChIKey IYRXGHQWARDYRT-UHFFFAOYSA-N
Formula C24H20O7
HBA 7
HBD 4
MW 420.42
Rotatable Bonds 3
TPSA 124.29
LogP 3.83
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 420.12
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 Kniphofia foliosa Asphodelaceae Plantae 214838
5 Kniphofia foliosa Asphodelaceae Plantae 214838
6 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]
  • 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]
  • 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: 10093576
Nmrshiftdb2: 60063513
Bindingdb: 86110

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1Cc(c23)c(ccc3)-c4ccccc4

Level: 1

Mol. Weight: 420.42 g/mol

Structure

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 420.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 420.42 g/mol

Anti-hiv
Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.8
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.990
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.140
Plasma Protein Binding
81.74
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
7.840
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.850
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.070
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.790
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
-34.360
Rat (Acute)
2.460
Rat (Chronic Oral)
3.370
Fathead Minnow
5.020
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
538.820
Hydration Free Energy
-5.780
Log(D) at pH=7.4
3.200
Log(P)
4.79
Log S
-6.43
Log(Vapor Pressure)
-8.94
Melting Point
220.76
pKa Acid
7.2
pKa Basic
6.38
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 0.9305
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9305
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9027
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9027
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8610
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8610
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8189
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8189
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8159
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8159
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.8024
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 4 0.8024
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7860
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7860
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7840
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7840
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7820
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7820
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7775
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7775
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7774
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7774
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7705
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7705
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7697
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7697
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7693
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7693
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7693
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7693
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7534
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7534
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7457
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7457
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7443
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7443
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7386
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7386
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7383
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7383
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7321
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7321
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7319
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7319
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7299
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7299
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7275
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7275
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.7270
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 4 0.7270
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7245
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7245
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7174
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7174
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7173
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7173
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7170
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7170
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7161
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7161
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7122
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7122
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7104
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7104
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7075
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7075

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