Knipholone tetraacetate - Compound Card

Knipholone tetraacetate

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Knipholone tetraacetate

Structure
Zoomed Structure
  • Family: Plantae - Liliaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(OC(=O)C)c(c(c1C(=O)C)OC(=O)C)c1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)OC(=O)C)OC(=O)C
InChI InChI=1S/C32H26O12/c1-13-11-22(42-16(4)35)27-29(30(38)19-9-8-10-20(41-15(3)34)26(19)31(27)39)24(13)28-23(43-17(5)36)12-21(40-7)25(14(2)33)32(28)44-18(6)37/h8-12H,1-7H3
InChIKey STVITSLQFSAAKK-UHFFFAOYSA-N
Formula C32H26O12
HBA 12
HBD 0
MW 602.55
Rotatable Bonds 7
TPSA 165.64
LogP 4.35
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 602.14
Number of Lipinski Rule Violations 2
# 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: 602.55 g/mol

Structure

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

Level: 0

Mol. Weight: 602.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 602.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.600
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
4.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.670
Plasma Protein Binding
62.68
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.650
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.410
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.390
Micronucleos
Toxic
NR-AhR
Safe
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
-12175.030
Rat (Acute)
3.110
Rat (Chronic Oral)
2.970
Fathead Minnow
36.020
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
472.770
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.890
Log(P)
3.0
Log S
-6.85
Log(Vapor Pressure)
-12.92
Melting Point
239.8
pKa Acid
7.38
pKa Basic
1.69
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 0.9407
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9407
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9277
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9277
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9101
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9101
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9012
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9012
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8429
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8429
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7953
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7953
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7915
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7915
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7870
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7870
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7861
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7861
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7628
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7628
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7574
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7574
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7571
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7571
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7543
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7543
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7508
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7508
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7374
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7374
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7343
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7343
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7257
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7257
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7234
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7234
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7208
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7208
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7176
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7176
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7144
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7144
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7097
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7097
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7066
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7066
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7051
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7051
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7033
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7033
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7013
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7013

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