Dehydro-beta-lapachone diacetate - Compound Card

Dehydro-beta-lapachone diacetate

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Dehydro-beta-lapachone diacetate

Structure
Zoomed Structure
  • Family: Plantae - Bignoniaceae
  • Kingdom: Plantae
  • Class: Quinone
Canonical Smiles CC(=O)Oc1c2C=CC(Oc2c2c(c1OC(=O)C)cccc2)(C)C
InChI InChI=1S/C19H18O5/c1-11(20)22-17-14-8-6-5-7-13(14)16-15(18(17)23-12(2)21)9-10-19(3,4)24-16/h5-10H,1-4H3
InChIKey LQOTXCCXLOWTHY-UHFFFAOYSA-N
Formula C19H18O5
HBA 5
HBD 0
MW 326.35
Rotatable Bonds 2
TPSA 61.83
LogP 3.87
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 326.12
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: 25110627

No compound-protein relationship available.

Structure

SMILES: O1CC=Cc(c1c23)ccc2cccc3

Level: 0

Mol. Weight: 326.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.02
Plasma Protein Binding
40.28
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
Non-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
9.61
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.84
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.62
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.63
Rat (Acute)
3.72
Rat (Chronic Oral)
2.01
Fathead Minnow
4.93
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
405.07
Hydration Free Energy
-7.71
Log(D) at pH=7.4
3.03
Log(P)
4.02
Log S
-5.36
Log(Vapor Pressure)
-6.34
Melting Point
145.97
pKa Acid
9.09
pKa Basic
3.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8738
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8172
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8099
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8067
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7928
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7872
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7839
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7727
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7602
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7520
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7355
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7317
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7305
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7268
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7234
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7233
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7196
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7187
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7156
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7111
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7097
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7076
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7025

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