Seco-anthraquinone - Compound Card

Seco-anthraquinone

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Seco-anthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles Cc1cc(O)c2c(c1)oc(=O)c1c(c2=O)c(O)ccc1
InChI InChI=1S/C15H10O5/c1-7-5-10(17)13-11(6-7)20-15(19)8-3-2-4-9(16)12(8)14(13)18/h2-6,16-17H,1H3
InChIKey GXBVJTTXZBEHQB-UHFFFAOYSA-N
Formula C15H10O5
HBA 5
HBD 2
MW 270.24
Rotatable Bonds 0
TPSA 87.74
LogP 2.03
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 270.05
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: 75528775
Nmrshiftdb2: 80018686

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 270.24 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.44
Plasma Protein Binding
77.47
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.01
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.1
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
4.37
Rat (Acute)
2.35
Rat (Chronic Oral)
2.67
Fathead Minnow
4.5
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
428.85
Hydration Free Energy
-9.93
Log(D) at pH=7.4
2.57
Log(P)
3.32
Log S
-4.92
Log(Vapor Pressure)
-7.75
Melting Point
266.86
pKa Acid
9.33
pKa Basic
4.07
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 0.9368
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9368
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.9008
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.9008
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8851
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8851
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8783
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8783
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8597
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8597
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8563
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8563
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8560
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8560
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8512
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8512
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8459
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8459
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8454
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8454
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8135
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 4 0.8135
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8091
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8091
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8073
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8073
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.8029
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.8029
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.8004
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.8004
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7995
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7995
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7993
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7993
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7983
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7983
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7974
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7974
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7972
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7972
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7929
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7929
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7907
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7907
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7863
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7863
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7834
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7834
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7807
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7807
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7796
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7796
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7769
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7769
Transketolase 1 P23254 TKT1_YEAST Saccharomyces cerevisiae 4 0.7734
Transketolase 1 P23254 TKT1_YEAST Saccharomyces cerevisiae 4 0.7734
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7721
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7721
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7700
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7700
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7693
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7693
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7685
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7685
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7683
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7683
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7679
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7679
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7671
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7671
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7650
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7650
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7591
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7591
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7585
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 4 0.7585
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7473
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7473
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7470
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7470
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7466
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7466
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7465
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7465
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7464
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7464
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7464
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7464
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7462
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7462
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7376
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7376
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7375
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7375
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7352
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7352
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7349
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7349
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7349
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7349
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7344
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7344
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7335
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7335
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7318
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7318
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7316
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7316
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7287
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7287
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7261
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7261
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7260
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7260
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7247
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7247
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7235
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7235
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7230
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7230
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7206
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7206
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7200
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7200
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7193
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7193
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7181
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7181
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 4 0.7178
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 4 0.7178
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7173
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7173
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7156
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7156
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7155
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7155
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7143
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7143
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7139
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7139
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7130
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7130
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7119
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7119
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7114
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7114
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7087
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7087
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7083
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7083
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7069
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7069
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7054
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7054
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7051
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7051
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7036
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7036
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7014
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7014
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7014
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7014
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7014
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7014
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7000
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7000

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