Knipholone tetramethyl ether - Compound Card

Knipholone tetramethyl ether

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Knipholone tetramethyl ether

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(C)c(c2c1C(=O)c1c(C2=O)cccc1OC)c1c(OC)cc(c(c1OC)C(=O)C)OC
InChI InChI=1S/C28H26O8/c1-13-11-17(33-4)23-25(26(30)15-9-8-10-16(32-3)22(15)27(23)31)20(13)24-19(35-6)12-18(34-5)21(14(2)29)28(24)36-7/h8-12H,1-7H3
InChIKey SJDZHUZPFHRFPE-UHFFFAOYSA-N
Formula C28H26O8
HBA 8
HBD 0
MW 490.51
Rotatable Bonds 7
TPSA 97.36
LogP 4.68
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 490.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Kniphofia foliosa Liliaceae Plantae 214838

Showing of synonyms

  • Dagne E, Steglich W. (1984). Knipholone: a unique anthraquinone derivative from Kniphofia foliosa.. Phytochemistry,1984,23(8),1729-1731. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 490.51 g/mol

Structure

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

Level: 0

Mol. Weight: 490.51 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 490.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.770
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.070
Plasma Protein Binding
72.43
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.690
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.720
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.430
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
-531.050
Rat (Acute)
3.410
Rat (Chronic Oral)
2.850
Fathead Minnow
7.340
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
561.880
Hydration Free Energy
-2.810
Log(D) at pH=7.4
3.290
Log(P)
4.24
Log S
-6.69
Log(Vapor Pressure)
-8.29
Melting Point
193.89
pKa Acid
7.77
pKa Basic
1.35
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 0.9240
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9240
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9122
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9122
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9020
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9020
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9003
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9003
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8915
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8915
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8741
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8741
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8655
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8655
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8526
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8526
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8349
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8349
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.8294
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.8294
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8169
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8169
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8063
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8063
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8040
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8040
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7887
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7887
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7853
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7853
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7828
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7828
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7823
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7823
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7764
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7764
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7653
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7653
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7625
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7625
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7624
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7624
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7620
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7620
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7577
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7577
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7550
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7550
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7541
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7541
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7516
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7516
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7492
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7492
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7470
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7470
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7452
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7452
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7444
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7444
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7442
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7442
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7432
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7432
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7406
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7406
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7365
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7365
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7324
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7324
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7300
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7300
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7287
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7287
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7276
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7276
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7260
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7260
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7227
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7227
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7206
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7206
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7200
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7200
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7199
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7199
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7189
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7189
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7167
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7167
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7139
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7139
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7131
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7131
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7122
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7122
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7113
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7113
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7093
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7093
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7081
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7081
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7076
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7076
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7063
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7063
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7046
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7046
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7016
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7016

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