Vismiaquinone C - Compound Card

Vismiaquinone C

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Vismiaquinone C

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1cc2c(c(c1CC=C(C)C)O)C(=O)c1c(C2=O)cc(cc1O)C
InChI InChI=1S/C21H20O5/c1-10(2)5-6-12-16(26-4)9-14-18(20(12)24)21(25)17-13(19(14)23)7-11(3)8-15(17)22/h5,7-9,22,24H,6H2,1-4H3
InChIKey ALEADBNEUMOAQO-UHFFFAOYSA-N
Formula C21H20O5
HBA 5
HBD 2
MW 352.39
Rotatable Bonds 3
TPSA 83.83
LogP 3.7
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 352.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Psorospermum aurantiacum Hypericaceae Plantae 999533

Showing of synonyms

  • Tiani G, Ahmed I, et al. (2013). Kenganthranol F, a new Anthranol from Psorospermum aurantiacum.. Natural Product Communications, 2013, 8(1), 103-104. [View] [PubMed]
Pubchem: 11783130
Nmrshiftdb2: 60047299

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 352.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.060
Plasma Protein Binding
67.69
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.110
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.240
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.810
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.280
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
2.340
Rat (Acute)
2.290
Rat (Chronic Oral)
3.070
Fathead Minnow
5.010
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
448.920
Hydration Free Energy
-9.610
Log(D) at pH=7.4
3.440
Log(P)
5.9
Log S
-7.08
Log(Vapor Pressure)
-7.87
Melting Point
175.93
pKa Acid
7.46
pKa Basic
4.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9640
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9133
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9098
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8944
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8790
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8715
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8586
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8524
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8376
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8364
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8242
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7968
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7946
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7834
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7834
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7777
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7714
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7670
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7609
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7577
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7534
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7482
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7481
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7427
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7411
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7409
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7382
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7379
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7376
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7362
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7270
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7270
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7235
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7235
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7222
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7216
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7183
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7170
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7141
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7135
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7124
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7114
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7093
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7080
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7023
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7010

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