10-hydroxy-10,7'-(chrysophanol anthrone)-chrysophanol - Compound Card

10-hydroxy-10,7'-(chrysophanol anthrone)-chrysophanol

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10-hydroxy-10,7'-(chrysophanol anthrone)-chrysophanol

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)c(cc1)[C@]1(O)c2cccc(c2C(=O)c2c1cc(C)cc2O)O
InChI InChI=1S/C30H20O8/c1-12-8-15-22(20(32)10-12)28(36)23-14(26(15)34)6-7-17(27(23)35)30(38)16-4-3-5-19(31)24(16)29(37)25-18(30)9-13(2)11-21(25)33/h3-11,31-33,35,38H,1-2H3/t30-/m1/s1
InChIKey KSTMMFCURGNHNW-SSEXGKCCSA-N
Formula C30H20O8
HBA 8
HBD 5
MW 508.48
Rotatable Bonds 1
TPSA 152.36
LogP 3.73
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.1
Exact Mass 508.12
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Kniphofia foliosa Asphodelaceae Plantae 214838

Showing of synonyms

  • 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]

No compound-protein relationship available.

Structure

SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)C(c(c45)cccc5)c6c(C4=O)cccc6

Level: 1

Mol. Weight: 508.48 g/mol

Structure

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

Level: 0

Mol. Weight: 508.48 g/mol

Structure

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

Level: 0

Mol. Weight: 508.48 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-6.1
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.05
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.2
Plasma Protein Binding
94.07
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.88
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.24
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.76
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.07
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
-1657.47
Rat (Acute)
2.44
Rat (Chronic Oral)
4.18
Fathead Minnow
9.67
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
587.77
Hydration Free Energy
-3.13
Log(D) at pH=7.4
3.31
Log(P)
6.68
Log S
-6.11
Log(Vapor Pressure)
-8.42
Melting Point
273.67
pKa Acid
9.28
pKa Basic
2.62
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8743
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8743
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8674
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8674
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8539
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8539
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8434
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8434
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8286
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8286
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8247
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8247
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8189
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8189
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8170
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8170
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7964
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7964
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7843
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7843
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7508
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7508
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7435
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7435
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7416
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7416
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7361
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7361
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7338
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7338
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7337
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7337
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7282
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7282
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7243
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7243
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7191
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7191
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7158
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7158
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7134
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7134
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7128
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7128
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7083
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7083
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7030
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7030
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7002
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7002

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