(E)-2-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalene-2-yl)vinyl acetate - Compound Card

(E)-2-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalene-2-yl)vinyl acetate

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(E)-2-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalene-2-yl)vinyl acetate

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles CC(=O)O/C=C/C1=C(O)C(=O)c2c(C1=O)cccc2
InChI InChI=1S/C14H10O5/c1-8(15)19-7-6-11-12(16)9-4-2-3-5-10(9)13(17)14(11)18/h2-7,18H,1H3/b7-6+
InChIKey ZBHPHZASMUPQBM-VOTSOKGWSA-N
Formula C14H10O5
HBA 5
HBD 1
MW 258.23
Rotatable Bonds 2
TPSA 80.67
LogP 1.95
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 258.05
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: 44588855

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)C=CC2=O

Level: 0

Mol. Weight: 258.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.27
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.38
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.02

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.07
Plasma Protein Binding
29.33
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-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
5.61
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.01
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.43
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.07
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
4.46
Rat (Acute)
2.74
Rat (Chronic Oral)
2.85
Fathead Minnow
4.45
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
357.94
Hydration Free Energy
-8.96
Log(D) at pH=7.4
1.3
Log(P)
1.81
Log S
-2.95
Log(Vapor Pressure)
-5.75
Melting Point
176.26
pKa Acid
4.22
pKa Basic
3.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9736
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9256
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8980
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8972
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8594
Pyridoxal kinase, putative C4LVZ4 C4LVZ4_ENTHI Entamoeba histolytica 3 0.8546
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.8409
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8163
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8059
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 3 0.7976
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7956
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7746
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7664
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7599
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.7530
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7397
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7361
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7298
Cysteine synthase 1 P47998 CYSK1_ARATH Arabidopsis thaliana 3 0.7230
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7206
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7204
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7190
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7179
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7178
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7169
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7166
Type IV pilus retractation ATPase PilT P24559 PILT_PSEAE Pseudomonas aeruginosa 3 0.7163
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7123
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7116
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7107
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7088
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7087
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7059
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7056
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7049
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7027
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 3 0.7014
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7013

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