2-(1'-methylethenyl)-naphtho[2,3-b]furan-4,9-dione - Compound Card

2-(1'-methylethenyl)-naphtho[2,3-b]furan-4,9-dione

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2-(1'-methylethenyl)-naphtho[2,3-b]furan-4,9-dione

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles CC(=C)c1cc2c(o1)C(=O)c1c(C2=O)cccc1
InChI InChI=1S/C15H10O3/c1-8(2)12-7-11-13(16)9-5-3-4-6-10(9)14(17)15(11)18-12/h3-7H,1H2,2H3
InChIKey JIXOWAXGILXNLY-UHFFFAOYSA-N
Formula C15H10O3
HBA 3
HBD 0
MW 238.24
Rotatable Bonds 1
TPSA 47.28
LogP 3.09
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 238.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Newbouldia leavis Bignoniaceae Plantae 211924

Showing of synonyms

  • 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: 637335
Nmrshiftdb2: 21334

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 238.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.37
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.02
Plasma Protein Binding
53.3
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
7.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.73
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.67
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.77
Micronucleos
Safe
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
4.81
Rat (Acute)
2.84
Rat (Chronic Oral)
2.31
Fathead Minnow
4.55
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
371.99
Hydration Free Energy
-8.87
Log(D) at pH=7.4
2.5
Log(P)
4.17
Log S
-5.69
Log(Vapor Pressure)
-7.35
Melting Point
182.84
pKa Acid
7.61
pKa Basic
3.81
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 0.9465
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9206
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9185
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9150
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.9081
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8920
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8825
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8774
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8619
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8471
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.8437
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8333
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8249
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8195
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8188
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8144
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8116
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8105
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8100
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8036
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.8027
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7978
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7963
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7950
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 4 0.7949
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7929
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7842
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7825
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7813
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7808
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7786
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7778
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7768
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7766
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7765
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7749
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7745
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7744
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7726
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7726
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7720
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7712
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7708
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7686
2-Hydroxyacid oxidase 1 Q9UJM8 HAOX1_HUMAN Homo sapiens 3 0.7680
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7679
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7663
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7658
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7647
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7640
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7614
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7592
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 3 0.7589
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 3 0.7587
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7587
Serine/threonine-protein kinase TBK1 Q9UHD2 TBK1_HUMAN Homo sapiens 3 0.7580
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7580
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7577
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7559
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7547
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7541
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7532
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7523
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7520
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7517
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7515
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7504
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7496
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7493
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7480
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7478
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7472
Ketimine reductase mu-crystallin O54983 CRYM_MOUSE Mus musculus 2 0.7472
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7467
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7460
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7459
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7453
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7441
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7428
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7427
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7425
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7407
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7393
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7365
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7359
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7354
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7340
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7338
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7335
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7329
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7325
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7317
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7309
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7309
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 4 0.7296
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7268
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7263
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7244
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7216
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7191
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7187
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7184
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7175
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7168
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7162
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7146
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7139
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7108
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7107
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7101
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7096
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7095
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7089
Enoyl-acyl carrier reductase Q6UCJ9 Q6UCJ9_TOXGO Toxoplasma gondii 3 0.7087
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7084
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7083
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7080
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7055
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.7053
Serine/threonine-protein kinase TBK1 Q9UHD2 TBK1_HUMAN Homo sapiens 3 0.7052
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 2 0.7052
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7050
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7047
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7047
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7046
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7046
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7042
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 2 0.7042
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7042
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7030
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7027
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7027
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 2 0.7021
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7017
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7016
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7010
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 2 0.7009
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7006
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7005
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7003

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