Isoknipholone anthrone - Compound Card

Isoknipholone anthrone

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Isoknipholone anthrone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthrone
Canonical Smiles COc1c(c(O)cc(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)23(21)30)18(10)22-17(29)9-16(28)19(11(2)25)24(22)31-3/h4-7,9,26-29H,8H2,1-3H3
InChIKey UGGPFDAKRGKKJS-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 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]
Pubchem: 101674077
Nmrshiftdb2: 60063514

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

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.83
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.970
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
82.18
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
8.100
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
0.910
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.840
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
Toxic
T. Pyriformis
-33.650
Rat (Acute)
2.470
Rat (Chronic Oral)
3.360
Fathead Minnow
5.000
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
531.010
Hydration Free Energy
-5.960
Log(D) at pH=7.4
3.280
Log(P)
5.03
Log S
-6.36
Log(Vapor Pressure)
-8.77
Melting Point
230.32
pKa Acid
8.82
pKa Basic
6.03
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 0.9663
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9663
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8735
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.8735
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8437
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8437
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8300
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8300
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8208
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8208
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8195
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8195
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8113
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8113
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8037
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8037
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8013
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8013
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7992
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7992
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7991
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7991
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7865
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7865
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7726
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7726
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7707
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7707
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7682
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7682
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7649
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7649
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7559
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7559
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7538
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7538
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7527
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7527
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7472
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7472
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7392
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7392
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7342
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7342
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7288
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7288
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7273
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7273
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7259
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7259
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7253
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7253
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7246
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7246
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7237
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7237
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7232
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7232
Acetyl-CoA acetyltransferase, mitochondrial P24752 THIL_HUMAN Homo sapiens 3 0.7195
Acetyl-CoA acetyltransferase, mitochondrial P24752 THIL_HUMAN Homo sapiens 3 0.7195
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7175
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7175
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7151
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7151
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7144
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7144
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7135
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7135
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7130
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7130
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7109
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7109
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7087
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7087
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7073
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 4 0.7073
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7071
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7071
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7024
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7024

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