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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Dimeric Anthraquinones/Anthrone
Canonical Smiles COC1(c2cc(O)c3c(c2)C(=O)c2c(C3=O)c(O)cc(c2)C)c2cccc(c2C(=O)c2c1cc(C)cc2O)O
InChI InChI=1S/C31H22O8/c1-13-7-16-24(21(33)9-13)29(37)25-17(28(16)36)11-15(12-23(25)35)31(39-3)18-5-4-6-20(32)26(18)30(38)27-19(31)8-14(2)10-22(27)34/h4-12,32-35H,1-3H3
InChIKey ILDGXTMDLSRMNK-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

  • 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: 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)
-5.69
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.28
Plasma Protein Binding
80.19
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.04
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.8
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.24
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
-2769.63
Rat (Acute)
2.51
Rat (Chronic Oral)
3.77
Fathead Minnow
16.26
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
568.34
Hydration Free Energy
-3.06
Log(D) at pH=7.4
4.01
Log(P)
6.44
Log S
-6.8
Log(Vapor Pressure)
-8.17
Melting Point
276.78
pKa Acid
8.44
pKa Basic
3.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8478
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8478
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8351
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8351
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8230
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8230
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8213
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8213
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8181
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8181
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7865
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7865
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7748
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7748
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7650
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7650
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7553
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7553
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7483
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7483
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7430
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7430
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 4 0.7354
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 4 0.7354
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7331
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7331
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7246
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7246
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7219
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7219
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7213
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7213
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7204
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7204
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7186
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7186
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7185
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7185
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7112
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7112
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7072
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7072
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7033
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7033
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7011
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 4 0.7011

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