1-(2,3,4,9-tetrahydro-4,9-dioxonaphtho[2,3-b]furany-2-yl)-1-methylethyl nitrate - Compound Card

1-(2,3,4,9-tetrahydro-4,9-dioxonaphtho[2,3-b]furany-2-yl)-1-methylethyl nitrate

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1-(2,3,4,9-tetrahydro-4,9-dioxonaphtho[2,3-b]furany-2-yl)-1-methylethyl nitrate

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles O=N(=O)OC(C1CC2=C(O1)C(=O)c1c(C2=O)cccc1)(C)C
InChI InChI=1S/C15H13NO6/c1-15(2,22-16(19)20)11-7-10-12(17)8-5-3-4-6-9(8)13(18)14(10)21-11/h3-6,11H,7H2,1-2H3
InChIKey XSDSYJPLPOKHMY-UHFFFAOYSA-N
Formula C15H13NO6
HBA 6
HBD 0
MW 303.27
Rotatable Bonds 3
TPSA 95.74
LogP 2.1
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 303.07
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: 25110626

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 303.27 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.460
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.050
Plasma Protein Binding
43.39
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
4.430
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.580
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.990
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.490
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
4.290
Rat (Acute)
2.850
Rat (Chronic Oral)
2.230
Fathead Minnow
4.520
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
355.610
Hydration Free Energy
-7.550
Log(D) at pH=7.4
2.250
Log(P)
3.29
Log S
-4.56
Log(Vapor Pressure)
-6.26
Melting Point
146.59
pKa Acid
4.22
pKa Basic
3.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 3 0.9321
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8672
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8345
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.8276
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 3 0.8198
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8180
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8014
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7697
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7617
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7605
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 3 0.7528
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7478
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7283
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7224
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7205
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7199
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7194
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7151
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7146
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7044
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7022
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7018
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7018

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