2-acetyl-6-methoxynaphtho[2,3-b]furan-4,9-dione - Compound Card

2-acetyl-6-methoxynaphtho[2,3-b]furan-4,9-dione

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2-acetyl-6-methoxynaphtho[2,3-b]furan-4,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Quinone Derivative
Canonical Smiles COc1ccc2c(c1)C(=O)c1c(C2=O)oc(c1)C(=O)C
InChI InChI=1S/C15H10O5/c1-7(16)12-6-11-13(17)10-5-8(19-2)3-4-9(10)14(18)15(11)20-12/h3-6H,1-2H3
InChIKey MXOJSPQFKNLVEH-UHFFFAOYSA-N
Formula C15H10O5
HBA 5
HBD 0
MW 270.24
Rotatable Bonds 2
TPSA 73.58
LogP 2.27
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 270.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Markhamia tomentosa Bignoniaceae Plantae 2708893

Showing of synonyms

  • Tantangmo F, Lenta BN, et al. (2010). Antiprotozoal activities of some constituents of Markhamia tomentosa (Bignoniaceae).. Annals of tropical medicine and parasitology,2010, 104(5), 391-398. [View] [PubMed]
Pubchem: 14861204
Nmrshiftdb2: 60077815

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 270.24 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.580
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.030
Plasma Protein Binding
47.02
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
7.520
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.380
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.220
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
4.200
Rat (Acute)
2.640
Rat (Chronic Oral)
2.540
Fathead Minnow
4.550
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
409.980
Hydration Free Energy
-9.820
Log(D) at pH=7.4
2.020
Log(P)
2.7
Log S
-5.42
Log(Vapor Pressure)
-7.79
Melting Point
239.04
pKa Acid
5.76
pKa Basic
3.54
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9737
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9660
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9514
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9427
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.9405
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9347
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.9330
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9029
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8975
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8959
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8922
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8820
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8816
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8800
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8795
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8770
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8697
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8641
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8625
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8605
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8544
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8514
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.8512
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8510
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8488
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8445
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8166
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8134
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8059
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.8032
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7988
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7985
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7984
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7947
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7938
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7922
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7913
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7909
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7895
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7892
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 2 0.7879
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7827
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7816
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7749
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7724
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7710
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7704
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7704
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7698
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7685
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7675
Thymidylate kinase Q9HZN8 KTHY_PSEAE Pseudomonas aeruginosa 3 0.7660
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7658
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7649
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7636
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7620
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7616
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7590
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7585
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7582
A disintegrin and metalloproteinase with thrombospondin motifs 5 Q9UNA0 ATS5_HUMAN Homo sapiens 3 0.7563
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7544
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7537
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7535
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7532
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7530
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7527
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7527
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7504
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7488
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7458
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7448
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7442
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7431
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7430
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7428
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7417
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7398
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7378
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7354
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7353
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7339
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7338
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7324
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7320
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7319
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7310
Farnesyl pyrophosphate synthase P14324 FPPS_HUMAN Homo sapiens 2 0.7309
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7282
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7277
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7273
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7270
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7265
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7265
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7260
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7245
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7242
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7218
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7217
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7215
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7209
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7206
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7203
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 2 0.7202
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7195
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7189
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 2 0.7189
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7173
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7170
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7168
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 2 0.7165
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7162
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7160
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7158
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7157
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7136
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7133
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7133
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7126
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7123
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7104
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7102
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7094
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 2 0.7093
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7089
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7077
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7073
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.7041
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7038
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7036
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7034
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 2 0.7024
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7019
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7010

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