Wentiquinone C - Compound Card

Wentiquinone C

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Wentiquinone C

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles OCc1cc(O)c2c(c1)oc(=O)c1c(c2=O)c(O)cc(c1)OC
InChI InChI=1S/C16H12O7/c1-22-8-4-9-13(11(19)5-8)15(20)14-10(18)2-7(6-17)3-12(14)23-16(9)21/h2-5,17-19H,6H2,1H3
InChIKey UBSXDIYXWMXBRI-UHFFFAOYSA-N
Formula C16H12O7
HBA 7
HBD 3
MW 316.27
Rotatable Bonds 2
TPSA 117.2
LogP 1.22
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 316.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine frutescens Asphodelaceae Plantae 210954

Showing of synonyms

  • Abdissa N, Heydenreich M, et al. (2014). A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters,2014,9,67-73. [View] [PubMed]
Pubchem: 102218165
Nmrshiftdb2: 70075328

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)c(=O)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 316.27 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.25
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.24
Plasma Protein Binding
73.66
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.77
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.74
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.97
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.24
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
3.18
Rat (Acute)
2.32
Rat (Chronic Oral)
3.0
Fathead Minnow
4.36
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
474.75
Hydration Free Energy
-10.3
Log(D) at pH=7.4
2.04
Log(P)
1.99
Log S
-5.06
Log(Vapor Pressure)
-7.95
Melting Point
239.1
pKa Acid
9.4
pKa Basic
2.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.9548
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.9548
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9022
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9022
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8915
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8915
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8836
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8836
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8766
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8766
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8658
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8658
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8576
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8576
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8507
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8507
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8389
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8389
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8319
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8319
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8228
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8228
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8182
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8182
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8056
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8056
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8039
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8039
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8021
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8021
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7951
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7951
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7949
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7949
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7920
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7920
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7917
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7917
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7818
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7818
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7795
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7795
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7742
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7742
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7723
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.7723
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7685
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7685
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7679
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7679
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7678
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7678
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7675
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7675
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7669
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7669
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7667
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7667
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7647
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7647
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7634
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7634
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7621
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7621
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7613
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7613
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7555
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7555
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7545
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7545
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7543
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7543
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7531
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7531
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7517
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7517
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7448
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7448
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7429
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7429
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7381
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7381
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7347
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7347
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7300
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7300
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7274
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7274
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7274
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7274
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7273
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7273
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7272
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7272
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7270
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7270
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7246
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7246
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7241
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7241
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7231
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7231
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7229
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7229
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7205
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7205
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7190
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 5 0.7190
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7182
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7182
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7175
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7175
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7152
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7152
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7120
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7120
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7109
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7109
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7107
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7107
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7087
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7087
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7085
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7085
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7075
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7075
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7058
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7058
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7006
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7006

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