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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Dimeric Anthraquinone
Canonical Smiles COC1(c2ccc3c(c2O)C(=O)c2c(C3=O)cc(cc2O)C)c2cccc(c2C(=O)c2c1cc(C)cc2O)O
InChI InChI=1S/C31H22O8/c1-13-9-16-23(21(33)11-13)29(37)24-15(27(16)35)7-8-18(28(24)36)31(39-3)17-5-4-6-20(32)25(17)30(38)26-19(31)10-14(2)12-22(26)34/h4-12,32-34,36H,1-3H3
InChIKey SAQGTQHYMPKIMS-UHFFFAOYSA-N
Formula C31H22O8
HBA 8
HBD 4
MW 522.51
Rotatable Bonds 2
TPSA 141.36
LogP 4.38
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 522.13
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]
Pubchem: 163032533

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: 522.51 g/mol

Structure

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

Level: 0

Mol. Weight: 522.51 g/mol

Structure

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

Level: 0

Mol. Weight: 522.51 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.66
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
82.39
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.73
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.78
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.85
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.5
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
-2854.37
Rat (Acute)
2.52
Rat (Chronic Oral)
3.86
Fathead Minnow
16.48
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
556.67
Hydration Free Energy
-3.07
Log(D) at pH=7.4
3.99
Log(P)
6.9
Log S
-6.74
Log(Vapor Pressure)
-7.97
Melting Point
269.16
pKa Acid
8.39
pKa Basic
3.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8678
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8678
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8673
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8673
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8262
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8262
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7972
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7972
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7915
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7915
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7789
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7789
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7749
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7749
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7657
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7657
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7502
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7502
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7495
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7495
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7350
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7350
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7311
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.7311
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7295
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7295
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7241
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7241
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7167
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7167
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 4 0.7119
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 4 0.7119
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7102
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7102
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7083
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7083

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