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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles CC(=C)C1CC2=C(O1)C(=O)c1c(C2=O)cccc1
InChI InChI=1S/C15H12O3/c1-8(2)12-7-11-13(16)9-5-3-4-6-10(9)14(17)15(11)18-12/h3-6,12H,1,7H2,2H3
InChIKey ZDMOREUAQLXRCQ-UHFFFAOYSA-N
Formula C15H12O3
HBA 3
HBD 0
MW 240.26
Rotatable Bonds 1
TPSA 43.37
LogP 2.68
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 240.08
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: 364109
Nmrshiftdb2: 70120454

No compound-protein relationship available.

Structure

SMILES: C1COC(=C12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 240.26 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.49
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.0
Plasma Protein Binding
49.77
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
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
6.26
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.22
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.36
Micronucleos
Safe
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
4.81
Rat (Acute)
2.85
Rat (Chronic Oral)
2.39
Fathead Minnow
4.47
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
341.72
Hydration Free Energy
-6.82
Log(D) at pH=7.4
2.28
Log(P)
3.52
Log S
-4.39
Log(Vapor Pressure)
-5.7
Melting Point
138.43
pKa Acid
6.04
pKa Basic
3.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8883
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8842
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8590
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8212
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7986
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7904
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7801
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7795
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7792
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7750
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7722
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7529
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7431
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7418
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7365
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7356
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7326
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7305
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7281
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7261
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7249
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7226
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7221
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7204
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7192
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7167
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7140
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7135
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7108
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7087
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7077
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7038
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7015
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7007

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