alpha-Lapachone

Details

• Internal ID: adb8c591-b586-4827-868a-35dab8381ec3
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: 2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
• SMILES (Canonical): CC1(CCC2=C(O1)C(=O)C3=CC=CC=C3C2=O)C
• SMILES (Isomeric): CC1(CCC2=C(O1)C(=O)C3=CC=CC=C3C2=O)C
• InChI: InChI=1S/C15H14O3/c1-15(2)8-7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-15/h3-6H,7-8H2,1-2H3
• InChI Key: PJWHOPKRRBUSDH-UHFFFAOYSA-N
• Popularity: 52 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: 2.60
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 4707-33-9
• .alpha.-Lapachone
• Lapachoone alpha
• 2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
• 2H-Naphtho[2,3-b]pyran-5,10-dione, 3,4-dihydro-2,2-dimethyl-
• UNII-VPE3AOX9QV
• VPE3AOX9QV
• NSC26327
• 2,2-Dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
• NSC629747
• NSC 26327
• NSC-26327
• NSC 629747
• NSC-629747
• 2,2-dimethyl-2H,3H,4H,5H,10H-naphtho[2,3-b]pyran-5,10-dione
• NSC 26327; NSC 629747
• 2H-Naphtho(2,3-b)pyran-5,10-dione, 3,4-dihydro-2,2-dimethyl-
• Alpha lapachone
• LAPACHONE, ALPHA
• LAPACHONE, .alpha.
• SCHEMBL102553
• CHEMBL441441
• BDBM24810
• DTXSID00197020
• CHEBI:182892
• PJWHOPKRRBUSDH-UHFFFAOYSA-N
• GLXC-17776
• HY-N2848
• Pyranonaphthoquinone derivative, 51
• AKOS028108462
• CCG-231496
• AC-37066
• MS-23427
• CS-0023426
• E76367
• 2H-Naphtho[2,10-dione, 3,4-dihydro-2,2-dimethyl-
• Q27291952
• 2,2-Dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione #
• 3,4-dihydro-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.8237	82.37%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7762	77.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9468	94.68%
OATP1B3 inhibitior	+	0.9801	98.01%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7982	79.82%
P-glycoprotein inhibitior	-	0.9350	93.50%
P-glycoprotein substrate	-	0.9788	97.88%
CYP3A4 substrate	+	0.5073	50.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8156	81.56%
CYP3A4 inhibition	+	0.5174	51.74%
CYP2C9 inhibition	+	0.8394	83.94%
CYP2C19 inhibition	+	0.8571	85.71%
CYP2D6 inhibition	+	0.8056	80.56%
CYP1A2 inhibition	+	0.8558	85.58%
CYP2C8 inhibition	-	0.9527	95.27%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9218	92.18%
Carcinogenicity (trinary)	Non-required	0.5972	59.72%
Eye corrosion	-	0.9818	98.18%
Eye irritation	+	0.7521	75.21%
Skin irritation	-	0.6337	63.37%
Skin corrosion	-	0.8973	89.73%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5408	54.08%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6073	60.73%
skin sensitisation	-	0.5410	54.10%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.6367	63.67%
Acute Oral Toxicity (c)	III	0.6215	62.15%
Estrogen receptor binding	+	0.8007	80.07%
Androgen receptor binding	+	0.7441	74.41%
Thyroid receptor binding	-	0.5740	57.40%
Glucocorticoid receptor binding	-	0.6783	67.83%
Aromatase binding	-	0.5460	54.60%
PPAR gamma	+	0.6381	63.81%
Honey bee toxicity	-	0.8259	82.59%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9491	94.91%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	4340 nM	IC50	PMID: 18318466

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.36%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.36%	98.95%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.30%	96.38%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.35%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.54%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	86.74%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.66%	86.33%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.30%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.39%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.37%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.96%	97.14%

Plants that contains it

• Catalpa ovata
• Ekmanianthe longiflora
• Firmiana simplex
• Handroanthus guayacan
• Handroanthus impetiginosus
• Tectona grandis

Cross-Links

• PubChem: 72732
• NPASS: NPC192577
• ChEMBL: CHEMBL441441
• LOTUS: LTS0255802
• wikiData: Q27291952