1-acetoxymethyl-8-hydroxynaphtho[2,3-c]furan-4,9-dione - Compound Card

1-acetoxymethyl-8-hydroxynaphtho[2,3-c]furan-4,9-dione

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1-acetoxymethyl-8-hydroxynaphtho[2,3-c]furan-4,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
    • Subclass: Isofuranonaphthoquinone
Canonical Smiles CC(=O)OCc1occ2c1C(=O)c1c(C2=O)cccc1O
InChI InChI=1S/C15H10O6/c1-7(16)20-6-11-13-9(5-21-11)14(18)8-3-2-4-10(17)12(8)15(13)19/h2-5,17H,6H2,1H3
InChIKey OYCTYROBRSPREE-UHFFFAOYSA-N
Formula C15H10O6
HBA 6
HBD 1
MW 286.24
Rotatable Bonds 2
TPSA 93.81
LogP 1.82
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 286.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bulbine capitata Asphodelaceae Plantae 576756

Showing of synonyms

  • Bezabih M, Abegaz BM, et al. (2001). Antiplasmodial and Antioxidant Isofuranonaphthoquinones from the Roots of Bulbine capitata. Planta medica, 2001, 67(4), 340–344. [View]
Pubchem: 10401719
Nmrshiftdb2: 70030870

No compound-protein relationship available.

Structure

SMILES: c1occ(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 286.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.77
Plasma Protein Binding
43.63
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
Non-Substrate
CYP 2C9 Inhibitor
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.83
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.44
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.06
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.72
Micronucleos
Toxic
NR-AhR
Safe
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
4.06
Rat (Acute)
2.9
Rat (Chronic Oral)
2.88
Fathead Minnow
4.5
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
407.0
Hydration Free Energy
-10.54
Log(D) at pH=7.4
1.64
Log(P)
3.02
Log S
-4.67
Log(Vapor Pressure)
-7.98
Melting Point
184.24
pKa Acid
5.42
pKa Basic
4.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9381
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9352
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9261
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9240
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9237
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9204
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9102
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9080
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.9049
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8964
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8942
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8813
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8773
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8748
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8719
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8699
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8699
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8629
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8572
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8569
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8478
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8458
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.8452
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8446
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8438
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8434
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8433
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8391
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8389
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8363
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8340
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8304
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8296
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8289
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.8142
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8121
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.8077
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8063
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8042
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.8014
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.8001
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7991
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7989
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7986
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7985
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7974
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7926
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7870
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7853
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7815
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7796
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7793
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7790
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7772
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7751
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7711
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7698
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7685
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7680
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7654
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7624
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 3 0.7621
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7619
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7619
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7616
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7603
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7596
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7581
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7568
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7554
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7507
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7502
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7486
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7485
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7484
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7477
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7457
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7454
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7450
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7447
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7444
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7436
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7435
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7433
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7429
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7413
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7391
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7390
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7390
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7374
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7372
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7359
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7356
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7348
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7334
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7331
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7314
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7314
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7289
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7281
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7268
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7257
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7254
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7240
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7234
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7228
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7223
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7210
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7210
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7207
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7206
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7199
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 2 0.7185
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7183
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7181
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7174
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7171
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7171
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7162
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7160
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7155
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7143
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7140
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7139
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7138
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7137
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7136
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7128
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7124
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7121
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7120
Geranyl diphosphate 2-C-methyltransferase D3KYU3 GPPMT_STRLS Streptomyces lasalocidi 3 0.7116
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7115
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7113
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7110
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7099
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7095
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7083
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7082
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7080
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7074
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7073
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7072
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 2 0.7071
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 4 0.7069
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 2 0.7067
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7062
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7058
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7054
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7042
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7039
Catabolite activator protein C3SQJ7 C3SQJ7_ECOLX Escherichia coli 3 0.7039
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7038
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7020
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7015
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7014
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7012
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7011

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