NP-MRD: Showing NP-Card for beta-Lapachone (NP0051619)

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Record Information

Version

2.0

Created at

2022-04-27 22:55:19 UTC

Updated at

2022-04-27 22:55:20 UTC

NP-MRD ID

NP0051619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Lapachone

Description

Lapachone, also known as ARQ 501 or beta-lap, belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Lapachone is an extremely weak basic (essentially neutral) compound (based on its pKa). beta-Lapachone is found in Catalpa longissima, Haplophragma adenophyllum, Markhamia platycalyx, Markhamia stipulata , Phyllarthron comorense , Tabebuia avellanedae , Tabebuia guayacan and Tectona grandis . beta-Lapachone was first documented in 2006 (PMID: 16822200). Lapachone has been used in trials studying the treatment of Cancer, Carcinoma, Advanced Solid Tumors, Head and Neck Neoplasms, and Carcinoma, Squamous Cell (PMID: 16891723) (PMID: 18180274) (PMID: 18227145) (PMID: 18424157) (PMID: 18706870) (PMID: 19051226).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.6466   -0.9781    1.1886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287   -0.6424   -0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763   -1.5869   -1.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4014    0.7990   -0.5702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228    1.6859    0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2772    1.3768    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596    0.1763    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283   -0.8054   -0.1641 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -0.1961    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9959   -1.4715   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127   -1.8798   -0.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2545   -0.9403    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8818    0.3594    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5464    0.7164    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194    2.0672    0.9474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9271    2.9537    1.2832 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053    2.4017    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    3.5550    1.1895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5552   -0.4115    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199   -2.0769    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8535   -0.7321    1.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826   -1.5469   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3030   -2.5947   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2121   -1.2505   -2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076    0.9331   -1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712    1.0061   -0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327    2.7611    0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093    1.5608    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300   -2.1980   -0.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893   -2.9088   -0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2910   -1.2368    0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    1.1039    0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
  8  2  1  0
 14  9  1  0
 17  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
M  END


  Mrv1533004151519002D          

 18 20  0  0  0  0            999 V2000
    4.3772   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3

> <INCHI_KEY>
QZPQTZZNNJUOLS-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.647652145475725

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.629317615333333

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8851459719292745

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
69.09200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-lapachone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    8                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    6   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione	ChEBI
ARQ 501	ChEBI
beta-Lap	ChEBI
b-Lap	Generator
Β-lap	Generator
b-Lapachone	Generator
β-lapachone	Generator

Chemical Formula

C₁₅H₁₄O₃

Average Mass

242.2740 Da

Monoisotopic Mass

242.09429 Da

IUPAC Name

2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione

Traditional Name

β-lapachone

CAS Registry Number

Not Available

SMILES

CC1(C)CCC2=C(O1)C1=CC=CC=C1C(=O)C2=O

InChI Identifier

InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3

InChI Key

QZPQTZZNNJUOLS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Catalpa longissima	LOTUS Database	35616633
Haplophragma adenophyllum	Plant	KNApSAcK
Markhamia platycalyx	LOTUS Database	35616633
Markhamia stipulata	Plant	KNApSAcK
Phyllarthron comorense	Plant	KNApSAcK
Tabebuia avellanedae	Plant	KNApSAcK
Tabebuia guayacan	Plant	KNApSAcK
Tectona grandis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Naphthalene
Quinone
Aryl ketone
Benzenoid
Pyran
Vinylogous ester
Ketone
Oxacycle
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinone (CHEBI:10429 )
benzochromenone (CHEBI:10429 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.82	ALOGPS
logP	2.63	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.09 m³·mol⁻¹	ChemAxon
Polarizability	25.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB11948

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002836

Chemspider ID

Not Available

KEGG Compound ID

C10367

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3885

PDB ID

Not Available

ChEBI ID

10429

Good Scents ID

Not Available

References

General References

Woo HJ, Park KY, Rhu CH, Lee WH, Choi BT, Kim GY, Park YM, Choi YH: Beta-lapachone, a quinone isolated from Tabebuia avellanedae, induces apoptosis in HepG2 hepatoma cell line through induction of Bax and activation of caspase. J Med Food. 2006 Summer;9(2):161-8. doi: 10.1089/jmf.2006.9.161. [PubMed:16822200 ]
Cunha-Filho MS, Landin M, Martinez-Pacheco R, Dacunha-Marinho B: Beta-lapachone. Acta Crystallogr C. 2006 Aug;62(Pt 8):o473-5. doi: 10.1107/S0108270106021706. Epub 2006 Jul 14. [PubMed:16891723 ]
Miao XS, Song P, Savage RE, Zhong C, Yang RY, Kizer D, Wu H, Volckova E, Ashwell MA, Supko JG, He X, Chan TC: Identification of the in vitro metabolites of 3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione (ARQ 501; beta-lapachone) in whole blood. Drug Metab Dispos. 2008 Apr;36(4):641-8. doi: 10.1124/dmd.107.018572. Epub 2008 Jan 7. [PubMed:18180274 ]
Savage RE, Tyler AN, Miao XS, Chan TC: Identification of a novel glucosylsulfate conjugate as a metabolite of 3,4-dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione (ARQ 501, beta-lapachone) in mammals. Drug Metab Dispos. 2008 Apr;36(4):753-8. doi: 10.1124/dmd.107.018655. Epub 2008 Jan 28. [PubMed:18227145 ]
Yang RY, Kizer D, Wu H, Volckova E, Miao XS, Ali SM, Tandon M, Savage RE, Chan TC, Ashwell MA: Synthetic methods for the preparation of ARQ 501 (beta-Lapachone) human blood metabolites. Bioorg Med Chem. 2008 May 15;16(10):5635-43. doi: 10.1016/j.bmc.2008.03.073. Epub 2008 Apr 1. [PubMed:18424157 ]
Savage RE, Hall T, Bresciano K, Bailey J, Starace M, Chan TC: Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of ARQ 501 (beta-lapachone) in plasma and tumors from nu/nu mouse xenografts. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Sep 1;872(1-2):148-53. doi: 10.1016/j.jchromb.2008.07.031. Epub 2008 Jul 31. [PubMed:18706870 ]
Miao XS, Zhong C, Wang Y, Savage RE, Yang RY, Kizer D, Volckova E, Ashwell MA, Chan TC: In vitro metabolism of beta-lapachone (ARQ 501) in mammalian hepatocytes and cultured human cells. Rapid Commun Mass Spectrom. 2009 Jan;23(1):12-22. doi: 10.1002/rcm.3835. [PubMed:19051226 ]
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Showing NP-Card for beta-Lapachone (NP0051619)

MOL for NP0051619 (beta-Lapachone)

3D MOL for NP0051619 (beta-Lapachone)

3D SDF for NP0051619 (beta-Lapachone)

3D-SDF for NP0051619 (beta-Lapachone)

PDB for NP0051619 (beta-Lapachone)

3D PDB for NP0051619 (beta-Lapachone)

SMILES for NP0051619 (beta-Lapachone)

INCHI for NP0051619 (beta-Lapachone)

Structure for NP0051619 (beta-Lapachone)

3D Structure for NP0051619 (beta-Lapachone)