beta-Lapachone

Details

• Internal ID: b468476a-f603-4a70-bb12-8a3c6ec21bf9
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
• SMILES (Canonical): CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C
• SMILES (Isomeric): CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C
• InChI: 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
• Popularity: 714 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27 g/mol
• Exact Mass: 242.094294304 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.75
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 4707-32-8
• lapachone
• 2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
• .beta.-Lapachone
• ARQ-501
• Lapachone, beta-
• ARQ 501
• Beta-lap-wj
• 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-B]pyran-5,6-dione
• NSC-26326
• LAPACHONE, BETA
• 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione
• 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione
• NSC 26326
• ARQ-501 (beta lapachone)
• 2H-Naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-
• SL 11001
• 3,4-Dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione
• UNII-6N4FA2QQ6A
• NSC 629749
• NSC-629749
• BRN 0181499
• 6N4FA2QQ6A
• MB-12066
• CHEBI:10429
• NSC26326
• NSC629749
• ARQ-501;NSC-26326
• 2H-Naphtho(1,2-b)pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-
• 5-17-11-00459 (Beilstein Handbook Reference)
• SR-01000075957
• Beta lapachone
• A-lapachone
• b-Lapachone
• beta-lap
• ss-Lapachone
• Beta -Lapachone
• ?-Lapachone
• Lapachone, .beta.
• MB12066
• LAPACHONE [INCI]
• Lopac-L-2037
• D0W0VD
• Lopac0_000717
• BSPBio_001306
• KBioGR_000026
• KBioSS_000026
• 2005rm01ch01
• MLS006011731
• R115 (Reactive Blue 2)
• CHEMBL15192
• SCHEMBL107042
• ARQ501
• BETA LAPACHONE [WHO-DD]
• BCBcMAP01_000055
• BDBM81348
• KBio2_000026
• KBio2_002594
• KBio2_005162
• KBio3_000051
• KBio3_000052
• DTXSID90197019
• beta-Lapachone, >=98% (TLC)
• Bio2_000026
• Bio2_000506
• HMS1361B08
• HMS1791B08
• HMS1989B08
• HMS3262O15
• HMS3402B08
• HMS3653O04
• HMS3866G13
• BCP09779
• EX-A3011
• Tox21_500717
• CCG-36362
• HSCI1_000182
• NSC813862
• s7261
• (c)micro-Lapachone pound>>ARQ 501
• AKOS005266281
• AC-8965
• CS-3680
• DB11948
• LP00717
• NSC-813862
• SDCCGSBI-0050695.P003
• IDI1_033776
• QTL1_000048
• beta-Lapachone (ARQ-501, CO-501)
• NCGC00015598-01
• NCGC00015598-02
• NCGC00015598-03
• NCGC00015598-04
• NCGC00015598-05
• NCGC00015598-06
• NCGC00015598-07
• NCGC00015598-08
• NCGC00015598-17
• NCGC00094066-01
• NCGC00094066-02
• NCGC00094066-03
• NCGC00094066-04
• NCGC00094066-05
• NCGC00261402-01
• AS-70326
• BP-28431
• HY-13555
• LS-95515
• NCI60_009665
• SL-11001
• SMR001456339
• EU-0100717
• FT-0635405
• SW219806-1
• A13059
• C75251
• A827146
• AK-693/21096016
• SR-01000075957-1
• SR-01000075957-5
• 2H-Naphtho[1,6-dione, 3,4-dihydro-2,2-dimethyl-
• Q27089386
• 2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione #
• 3,4-Dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6dione
• 2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione
• AfAE'A centa' notA inverted exclamation markAfasA'A|AfAE'Adaggeratrade markAfA centA centasA notA em leaderA inverted exclamation mark-Lapachone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.7070	70.70%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7994	79.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9359	93.59%
OATP1B3 inhibitior	+	0.9819	98.19%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8488	84.88%
P-glycoprotein inhibitior	-	0.9456	94.56%
P-glycoprotein substrate	-	0.9706	97.06%
CYP3A4 substrate	+	0.5132	51.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7755	77.55%
CYP3A4 inhibition	+	0.6108	61.08%
CYP2C9 inhibition	+	0.8628	86.28%
CYP2C19 inhibition	+	0.8736	87.36%
CYP2D6 inhibition	+	0.8308	83.08%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9390	93.90%
CYP inhibitory promiscuity	+	0.5378	53.78%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9318	93.18%
Carcinogenicity (trinary)	Non-required	0.5923	59.23%
Eye corrosion	-	0.9865	98.65%
Eye irritation	+	0.7012	70.12%
Skin irritation	-	0.5999	59.99%
Skin corrosion	-	0.8815	88.15%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5480	54.80%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.6407	64.07%
skin sensitisation	-	0.5485	54.85%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.7976	79.76%
Acute Oral Toxicity (c)	III	0.6077	60.77%
Estrogen receptor binding	+	0.8223	82.23%
Androgen receptor binding	+	0.7512	75.12%
Thyroid receptor binding	-	0.5321	53.21%
Glucocorticoid receptor binding	-	0.6142	61.42%
Aromatase binding	-	0.5461	54.61%
PPAR gamma	+	0.7218	72.18%
Honey bee toxicity	-	0.8367	83.67%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9700	97.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2524	P06280	Alpha-galactosidase A	8912.5 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	15848.9 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	17782.8 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	25118.9 nM; 25118.9 nM; 25118.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL3180	O00748	Carboxylesterase 2	109 nM	Ki	via Super-PRED
CHEMBL4096	P04637	Cellular tumor antigen p53	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	3981.07 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	3981.07 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	31622.78 nM	AC50	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	15848.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293278	O75496	Geminin	31622.8 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	100 nM; 100 nM	Ki; Ki	PMID: 25970480; via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	3000 nM; 3000 nM	IC50; IC50	PMID: 21596573; DOI: 10.1039/C1MD00199J
CHEMBL4040	P28482	MAP kinase ERK2	31622.8 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	5011.9 nM; 12589.3 nM; 11220.2 nM; 10000 nM; 15848.9 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL3632452	Q9UDY8	Mucosa-associated lymphoid tissue lymphoma translocation protein 1	1200 nM; 1900 nM	IC50; IC50	PMID: 26496175; PMID: 26496175
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	3162.3 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	8912.5 nM; 8912.5 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	37933 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	25118.9 nM; 5 nM; 5 nM	Potency; Potency; Potency	via CMAUP; via Super-PRED; via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	26121.6 nM; 13091.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	15848.9 nM; 25118.9 nM; 7079.5 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	1584.9 nM; 1584.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	5011.9 nM; 35481.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	39810.7 nM	Potency	via CMAUP
CHEMBL2169736	O95551	Tyrosyl-DNA phosphodiesterase 2	970 nM; 970 nM	IC50; IC50	PMID: 23859074; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.30%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.32%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.34%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.61%	99.23%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.76%	82.69%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.86%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.72%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	82.58%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.48%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.39%	97.14%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.30%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.99%	89.00%

Plants that contains it

• Catalpa longissima
• Handroanthus guayacan
• Handroanthus impetiginosus
• Markhamia lutea
• Markhamia stipulata
• Tectona grandis

Cross-Links

• PubChem: 3885
• NPASS: NPC212415
• ChEMBL: CHEMBL15192
• LOTUS: LTS0183748
• wikiData: Q27089386