Lapachol

Details

• Internal ID: 84871b78-718c-407a-8d61-c1bfa41e287e
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
• SMILES (Canonical): CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C
• InChI: InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,16H,8H2,1-2H3
• InChI Key: CWPGNVFCJOPXFB-UHFFFAOYSA-N
• Popularity: 563 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): 54.40 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.08
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 84-79-7
• Greenhartin
• Tecomin
• Bethabarra wood
• Taiguic acid
• Lapachol wood
• Taigu wood
• C.I. Natural Yellow 16
• Lapachic acid
• IPE-tobacco wood
• Greenharten
• Surinam greenheart wood
• NSC-11905
• C.I. 75490
• Zlut prirodni 16
• Tecomin (VAN)
• NSC 11905
• 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone
• Zlut prirodni 16 [Czech]
• 4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
• CCRIS 745
• 1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)-
• NSC 629756
• NSC11905
• EINECS 201-563-7
• NSC629756
• BRN 2051889
• 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione
• 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-
• CHEBI:6377
• DTXSID6049430
• UNII-B221938VB6
• 2-Hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone
• B221938VB6
• NSC-629756
• 2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione
• 2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione
• 4-08-00-02487 (Beilstein Handbook Reference)
• Groenhartin
• Lapachoic acid
• Lapachol, 98%
• Natural Yellow-?16
• 1,4-Naphthalenedione,2-hydroxy-3-(3-methyl-2-buten-1-yl)-
• LAPACHOL [MI]
• Spectrum2_001451
• Spectrum3_000768
• Spectrum5_001873
• bmse000989
• NCIMech_000076
• Oprea1_717083
• BSPBio_002416
• CHEMBL15193
• DivK1c_000594
• SCHEMBL157255
• SCHEMBL157256
• SPECTRUM1501204
• SPBio_001341
• 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphtho-quinone
• DTXCID5029390
• HMS501N16
• KBio1_000594
• KBio3_001636
• NINDS_000594
• HMS1921B06
• HMS3869D03
• AMY40588
• BCP24022
• HY-N6961
• Tox21_202948
• CCG-35464
• MFCD00001679
• s5684
• AKOS015951424
• AKOS032948320
• AC-8971
• CI75490
• CS-W020951
• SDCCGMLS-0066666.P001
• CAS-84-79-7
• IDI1_000594
• NCGC00094931-01
• NCGC00094931-02
• NCGC00094931-03
• NCGC00094931-04
• NCGC00094931-06
• NCGC00260494-01
• WLN: L66 BV EVJ CQ D2UY1&1
• AS-35308
• CI 75490
• LS-95648
• NCI60_000457
• NCI60_000587
• PD087478
• 1, 2-hydroxy-3-(3-methyl-2-butenyl)-
• FT-0649649
• A863979
• Cancer Chemother Rep (part 2) 4: 11 (1974)
• Q739601
• SR-05000002489
• 2-Hydroxy-3-(3-methyl-2-butenyl)naphthoquinone #
• SR-05000002489-1
• 2-hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinon
• NSC-11905; NSC 11905; NSC11905
• 2-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,4-dione
• 3-(3-Methyl-2-butenyl)-4-hydroxy-1,2-naphthoquinone
• 4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8998	89.98%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8532	85.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9213	92.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6191	61.91%
P-glycoprotein inhibitior	-	0.8907	89.07%
P-glycoprotein substrate	-	0.9331	93.31%
CYP3A4 substrate	-	0.6113	61.13%
CYP2C9 substrate	-	0.8030	80.30%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.8820	88.20%
CYP2C9 inhibition	+	0.9264	92.64%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.6167	61.67%
CYP1A2 inhibition	+	0.9060	90.60%
CYP2C8 inhibition	-	0.9626	96.26%
CYP inhibitory promiscuity	+	0.7016	70.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8928	89.28%
Carcinogenicity (trinary)	Non-required	0.6684	66.84%
Eye corrosion	-	0.9824	98.24%
Eye irritation	+	0.9412	94.12%
Skin irritation	-	0.5512	55.12%
Skin corrosion	-	0.8852	88.52%
Ames mutagenesis	-	0.8854	88.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8095	80.95%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	+	0.6766	67.66%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7577	75.77%
Acute Oral Toxicity (c)	III	0.5564	55.64%
Estrogen receptor binding	+	0.8373	83.73%
Androgen receptor binding	+	0.6273	62.73%
Thyroid receptor binding	-	0.5280	52.80%
Glucocorticoid receptor binding	+	0.8669	86.69%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8586	85.86%
Honey bee toxicity	-	0.8901	89.01%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9947	99.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.42%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.59%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	94.42%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.81%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	89.82%	94.73%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.44%	82.69%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.19%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.30%	99.23%

Plants that contains it

• Avicennia germinans
• Catalpa longissima
• Catalpa ovata
• Cybistax antisyphilitica
• Diphysa americana
• Dolichandra unguis-cati
• Handroanthus chrysotrichus
• Handroanthus guayacan
• Hibiscus tilliaceus
• Kigelia africana subsp. africana
• Magnolia liliiflora
• Markhamia lutea
• Markhamia stipulata
• Markhamia tomentosa
• Newbouldia laevis
• Oroxylum indicum
• Phyllarthron comorense
• Plenckia populnea
• Plumbago zeylanica
• Radermachera sinica
• Stereospermum kunthianum
• Tabebuia ochracea
• Tabebuia rosea
• Tecomella undulata
• Tectona grandis

Cross-Links

• PubChem: 3884
• NPASS: NPC216413
• LOTUS: LTS0207379
• wikiData: Q739601