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Dehydro-alpha-lapachone
- Family: Plantae - Bignoniaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Naphthoquinone
| Canonical Smiles | O=C1C2=C(C=CC(O2)(C)C)C(=O)c2c1cccc2 |
|---|---|
| InChI | InChI=1S/C15H12O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-8H,1-2H3 |
| InChIKey | OWFHAMHRUCUSRM-UHFFFAOYSA-N |
| Formula | C15H12O3 |
| HBA | 3 |
| HBD | 0 |
| MW | 240.26 |
| Rotatable Bonds | 0 |
| 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 | Kigelia pinnata | Bignoniaceae | Plantae | 70070 |
| 2 | Newbouldia leavis | Bignoniaceae | Plantae | 211924 |
Showing of synonyms
Dehydro-alpha-lapachone
Xyloidone
15297-92-4
Dehydrolapachone
2,2-dimethylbenzo[g]chromene-5,10-dione
Dehydro-.alpha.-lapachol
Dehydro-.alpha.-lapacone
Dehydro-.alpha.-lapachone
Xyloidone (VAN)
.alpha.-Lapachone, dehydro-
Dehydro-alpha-lapachol
Dehydro-alpha-lapacone
Alpha-Lapachone, dehydro-
NSC 106453
NSC 629748
XILOIDONE
305WY61CUF
2H-Naphtho[2,3-b]pyran-5,10-dione, 2,2-dimethyl-
LDN-22684
NSC-106453
NSC-629748
DTXSID30165176
2H-Naphtho(2,3-b)pyran-5,10-dione, 2,2-dimethyl-
2,2-DIMETHYL-2H-NAPHTHO(2,3-B)PYRAN-5,10-DIONE
Q 99 2,2-DIMETHYL-2H-NAPHTHO(2,3-B)PYRAN-5,10-DIONE
2,2-dimethylbenzo(g)chromene-5,10-dione
DTXCID9087667
2H-Naphtho(2,3-b)pyran-5,10-dione, 2,2-dimethyl-(8CI)
2H-Naphtho(2,3-b)pyran-5,10-dione, 2,2-dimethyl-(8CI)(9CI)
621-432-1
2,2-Dimethyl-2H-benzo[g]chromene-5,10-dione
Dehydro-|A-lapachone
DEHYDROPLAPACHONE
NSC106453
NSC629748
2H-Naphtho(2,3-b)pyran-5,10-dione, 2,2-dimethyl- (8CI)(9CI)
Dehydro-a-Lapachone
LDN 22684
Dehydro-?-lapachone
UNII-305WY61CUF
CHEMBL272253
SCHEMBL3617968
2,2-dimethyl-2H,5H,10H-benzo[g]chromene-5,10-dione
BDBM24786
OWFHAMHRUCUSRM-UHFFFAOYSA-N
GLXC-06861
HY-N3706
Pyranonaphthoquinone derivative, 23
QAA29792
MFCD00022286
AKOS024341158
FS-10412
2H-Naphtho[2,10-dione, 2,2-dimethyl-
DB-063966
CS-0024092
G67396
2,2-dimethyl-2h-benzo [g]chromene-5,10-dione
2,2-Dimethyl-2H-benzo[g]chromene-5,10-dione #
AP-607/40962863
DAL
-Lapachone, dehydro-
- Binutu OA, Adesogan KE, et al. (1996). Antibacterial and antifungal compounds from Kigelia pinnata. Planta Medica, 1996,62(4), 352-353. [View]
- 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:
72734
Cas:
15297-92-4
Zinc:
ZINC000000338411
Nmrshiftdb2:
60030426
Chembl:
CHEMBL272253
Comptox:
DTXSID30165176
Bindingdb:
24786
CPRiL:
156591
SMILES: c1cccc(c12)C(=O)C3=C(C2=O)C=CCO3
Level: 0
Mol. Weight: 240.26 g/mol
Antibacterial
Antifungal
Absorption
- Caco-2 (logPapp)
- -4.48
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.370
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.010
- Plasma Protein Binding
- 42.79
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 3.970
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.850
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.420
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.490
- 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
- 4.370
- Rat (Acute)
- 2.590
- Rat (Chronic Oral)
- 2.380
- Fathead Minnow
- 4.430
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 347.110
- Hydration Free Energy
- -7.000
- Log(D) at pH=7.4
- 2.450
- Log(P)
- 3.15
- Log S
- -4.29
- Log(Vapor Pressure)
- -4.99
- Melting Point
- 140.0
- pKa Acid
- 6.3
- pKa Basic
- 2.81
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8480 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7786 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7781 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7577 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7486 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7446 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7171 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7162 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7037 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7010 |