2-acetylnaphtho[2,3-b]furan-4,9-dione - Compound Card

2-acetylnaphtho[2,3-b]furan-4,9-dione

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2-acetylnaphtho[2,3-b]furan-4,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles CC(=O)c1cc2c(o1)C(=O)c1c(C2=O)cccc1
InChI InChI=1S/C14H8O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-6H,1H3
InChIKey DPHUWDIXHNQOSY-UHFFFAOYSA-N
Formula C14H8O4
HBA 4
HBD 0
MW 240.21
Rotatable Bonds 1
TPSA 64.35
LogP 2.26
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 240.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Markhamia tomentosa Bignoniaceae Plantae 2708893
2 Newbouldia leavis Bignoniaceae Plantae 211924
3 Newbouldia laevis Bignoniaceae Plantae 211924
4 Newbouldia laevis Bignoniaceae Plantae 211924

Showing of synonyms

  • Kuete V, Eyong KO, et al. (2007). Antimicrobial activity of the methanolic extract and of the chemical constituents isolated from Newbouldia laevis. Die Pharmazie - An International Journal of Pharmaceutical Sciences, 2007, 62(7), 552-556. [View]
  • 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]
  • Eyong KO, Folefoc GN, et al. (2006). Newbouldiaquinone A: A naphthoquinone-anthraquinone ether coupled pigment, as a potential antimicrobial and antimalarial agent from Newbouldia laevis.. Phytochemistry,2006, 67(6), 605-609. [View] [PubMed]
  • Eyong KO, Kumar PS, et al. (2008). Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol.. Bioorganic & medicinal chemistry letters,2008, 18(20), 5387-5390. [View] [PubMed]
Pubchem: 10331844
Nmrshiftdb2: 60030429
Drugbank: DB12155
Bindingdb: 50366597
CPRiL: 68457
Structure

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

Level: 0

Mol. Weight: 240.21 g/mol

Antitumor
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.46
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.07
Plasma Protein Binding
52.66
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
7.5
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.28
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.66
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
4.23
Rat (Acute)
3.01
Rat (Chronic Oral)
2.53
Fathead Minnow
4.51
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
376.74
Hydration Free Energy
-9.01
Log(D) at pH=7.4
1.63
Log(P)
2.5
Log S
-4.94
Log(Vapor Pressure)
-7.71
Melting Point
238.54
pKa Acid
5.64
pKa Basic
3.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.9572
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.9560
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9327
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9324
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.9240
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9160
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9111
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9089
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8988
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8922
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8903
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.8675
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8634
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8626
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8548
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8517
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8345
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8177
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8172
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8153
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.8091
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.8078
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 2 0.8072
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.8038
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8036
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8001
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7958
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7941
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7933
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7831
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7823
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7799
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7780
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7762
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7759
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7748
Thymidylate kinase Q9HZN8 KTHY_PSEAE Pseudomonas aeruginosa 3 0.7719
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7719
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7699
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7682
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7664
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7659
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7659
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7637
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7618
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7615
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7611
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7611
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7606
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7594
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7578
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7574
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7568
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7565
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7552
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7550
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7540
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7530
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7528
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7523
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7521
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7519
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7499
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7499
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7489
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7488
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 2 0.7478
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7477
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7435
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7433
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7421
A disintegrin and metalloproteinase with thrombospondin motifs 5 Q9UNA0 ATS5_HUMAN Homo sapiens 3 0.7418
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7408
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7399
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7395
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7392
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7375
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7369
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7366
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7363
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7357
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7348
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7344
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7342
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7340
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7301
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7300
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 4 0.7293
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7291
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7276
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7264
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7258
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7257
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7254
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7254
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 2 0.7239
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7239
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7239
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7235
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7229
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7227
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7224
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7219
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7213
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7202
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7198
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7198
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7168
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7166
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7152
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7143
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7136
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7128
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7128
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7125
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7124
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7119
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7113
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 2 0.7109
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7097
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7096
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7096
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 2 0.7091
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7090
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7086
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7085
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 2 0.7077
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7059
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7054
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7051
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7043
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7038
Cytochrome P450 2C5 P00179 CP2C5_RABIT Oryctolagus cuniculus 2 0.7034
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7020
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7004
(RS)-norcoclaurine 6-O-methyltransferase Q5C9L7 6OMT_THLFG Thalictrum flavum subsp. glaucum 3 0.7002
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7001

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