Wentiquinone A - Compound Card

Wentiquinone A

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Wentiquinone A

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles COc1cc(O)c2c(c1)c(=O)oc1c(c2=O)c(O)cc(c1)C
InChI InChI=1S/C16H12O6/c1-7-3-10(17)14-12(4-7)22-16(20)9-5-8(21-2)6-11(18)13(9)15(14)19/h3-6,17-18H,1-2H3
InChIKey YVFJBYLLLWUXQF-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 2
MW 300.27
Rotatable Bonds 1
TPSA 96.97
LogP 2.03
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 300.06
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: 139587427
Nmrshiftdb2: 70109239

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 300.27 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.480
Plasma Protein Binding
78.13
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
4.080
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.820
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.430
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
4.290
Rat (Acute)
2.310
Rat (Chronic Oral)
2.630
Fathead Minnow
4.610
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
447.220
Hydration Free Energy
-9.720
Log(D) at pH=7.4
2.900
Log(P)
3.3
Log S
-5.96
Log(Vapor Pressure)
-7.65
Melting Point
257.41
pKa Acid
9.47
pKa Basic
3.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9373
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9373
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9139
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9139
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8976
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8976
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8777
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8777
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8762
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8762
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8758
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8758
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8741
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8741
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8736
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8736
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8621
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8621
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8619
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8619
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8618
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8618
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8535
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8535
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8496
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8496
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8424
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8424
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8420
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8420
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8366
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8366
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8271
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8271
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8142
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8142
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8075
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8075
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8059
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8059
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8025
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8025
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7996
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7996
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7994
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7994
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7942
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7942
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7937
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7937
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7915
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7915
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7914
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7914
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7893
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7893
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7880
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7880
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7861
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7861
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7841
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7841
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7822
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7822
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7768
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7768
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7754
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7754
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7741
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7741
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7727
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7727
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7676
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7676
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7642
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7642
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7638
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7638
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7633
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7633
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7613
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7613
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7610
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7610
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7586
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7586
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7573
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7573
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7537
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7537
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7518
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7518
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7487
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7487
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7476
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7476
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7460
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7460
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7438
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7438
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7413
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7413
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7365
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7365
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7358
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7358
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7336
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7336
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7334
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7334
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7300
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7300
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7273
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7273
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7270
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7270
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7260
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7260
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7255
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7255
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7241
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7241
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7239
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7239
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7237
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7237
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7234
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7234
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7232
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7232
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7231
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7231
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7223
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7223
Transketolase 1 P23254 TKT1_YEAST Saccharomyces cerevisiae 4 0.7212
Transketolase 1 P23254 TKT1_YEAST Saccharomyces cerevisiae 4 0.7212
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7188
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7188
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7178
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7178
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7174
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7174
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7167
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7167
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7156
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7156
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7149
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7149
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7143
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7143
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7112
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7112
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7096
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7096
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7094
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7094
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7065
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7065
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7058
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7058
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7057
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7057
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7054
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7054
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7031
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7031
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7030
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7030
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7019
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7019
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7017
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7017

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