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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Dimeric Anthraquinones/Anthrone
Canonical Smiles Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)C1(O)c2cccc(c2C(=O)c2c1cc(C)cc2O)O
InChI InChI=1S/C30H20O8/c1-12-6-15-23(20(32)8-12)28(36)24-16(27(15)35)10-14(11-22(24)34)30(38)17-4-3-5-19(31)25(17)29(37)26-18(30)7-13(2)9-21(26)33/h3-11,31-34,38H,1-2H3
InChIKey QFWWYRULSZHMSH-UHFFFAOYSA-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

  • Induli M, Gebru M, et al. (2013). Antiplasmodial Quinones from the Rhizomes of Kniphofia foliosa. Natural Product Communications,2013,8(9),1261-1264. [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)
-6.08
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.03
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.21
Plasma Protein Binding
84.49
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
Non-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
7.74
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.2
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.73
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.96
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
-1616.47
Rat (Acute)
2.39
Rat (Chronic Oral)
4.43
Fathead Minnow
9.63
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
591.5
Hydration Free Energy
-3.11
Log(D) at pH=7.4
3.4
Log(P)
6.28
Log S
-6.15
Log(Vapor Pressure)
-8.46
Melting Point
278.39
pKa Acid
9.74
pKa Basic
2.42
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 0.8930
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8930
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8366
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8366
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8335
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8335
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8039
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8039
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7816
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7816
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7620
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7620
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7571
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7571
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7441
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7441
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7270
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7270
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7233
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7233

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