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Lapachol
- Family: Plantae - Bignoniaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Naphthoquinone
| Canonical Smiles | CC(=CCC1=C(O)c2c(C(=O)C1=O)cccc2)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 |
| InChIKey | CWPGNVFCJOPXFB-UHFFFAOYSA-N |
| Formula | C15H14O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 242.27 |
| Rotatable Bonds | 2 |
| TPSA | 54.37 |
| LogP | 3.08 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.2 |
| Exact Mass | 242.09 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Kigelia pinnata | Bignoniaceae | Plantae | 70070 |
| 2 | Newbouldia leavis | Bignoniaceae | Plantae | 211924 |
| 3 | Newbouldia laevis | Bignoniaceae | Plantae | 211924 |
| 4 | Newbouldia laevis | Bignoniaceae | Plantae | 211924 |
| 5 | Newbouldia laevis | Bignoniaceae | Plantae | 211924 |
Showing of synonyms
Lapachol
84-79-7
2-Hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone
Greenhartin
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
4-hydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
NSC 11905
2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone
1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)-
NSC 629756
NSC11905
2-hydroxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione
NSC629756
2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione
1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-
CHEBI:6377
DTXSID6049430
B221938VB6
NSC-629756
2-Hydroxy-3-(3-methyl-2-buten-1-yl)-1,4-naphthalenedione
Tecomin (VAN)
Zlut prirodni 16 [Czech]
CCRIS 745
EINECS 201-563-7
BRN 2051889
UNII-B221938VB6
Lapachol (Standard)
MFCD00001679
Lapachol, 98%
Natural Yellow-?16
LAPACHOL [MI]
Spectrum2_001451
Spectrum3_000768
Spectrum5_001873
Bmse000989
NCIMech_000076
Oprea1_717083
BSPBio_002416
4-08-00-02487 (Beilstein Handbook Reference)
CHEMBL15193
DivK1c_000594
SCHEMBL157255
SCHEMBL157256
SPECTRUM1501204
SPBio_001341
DTXCID5029390
HMS501N16
HY-N6961R
KBio1_000594
KBio3_001636
CWPGNVFCJOPXFB-UHFFFAOYSA-N
NINDS_000594
HMS1921B06
HMS3869D03
BCP24022
HY-N6961
Tox21_202948
CCG-35464
S5684
AKOS015951424
AKOS032948320
AC-8971
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
NCI60_000457
NCI60_000587
PD087478
1, 2-hydroxy-3-(3-methyl-2-butenyl)-
NS00021374
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)naphthalene-1,4-dione
4-hydroxy-3-(3-methylbut-2-en-1-yl)-1,2-dihydronaphthalene-1,2-dione
- Binutu OA, Adesogan KE, et al. (1996). Antibacterial and antifungal compounds from Kigelia pinnata. Planta Medica, 1996,62(4), 352-353. [View]
- Kuete V, Eyong KO, et al. (2007). Antimicrobial activity of the methanolic extract and of the chemical constituents isolated from Newbouldia laevis. Die Pharmazie - An International Journal of Pharmaceutical Sciences, 2007, 62(7), 552-556. [View]
- Eyong KO, Folefoc GN, et al. (2006). Newbouldiaquinone A: A naphthoquinone-anthraquinone ether coupled pigment, as a potential antimicrobial and antimalarial agent from Newbouldia laevis.. Phytochemistry,2006, 67(6), 605-609. [View] [PubMed]
- Eyong KO, Krohn K, et al. (2005). Newbouldiaquinone and newbouldiamide: a new naphthoquinone-anthraquinone coupled pigment and a new ceramide from Newbouldia laevis.. Chemical & pharmaceutical bulletin,2005, 53(6), 616-619. [View] [PubMed]
- 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]
CPRiL:
25315
SMILES: c1cccc(c12)C=CC(=O)C2=O
Level: 0
Mol. Weight: 242.27 g/mol
Antibacterial
Antifungal
Absorption
- Caco-2 (logPapp)
- -4.5
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.26
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.72
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.09
- Plasma Protein Binding
- 32.68
- 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
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.37
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.34
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.23
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.37
- 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
- 4.45
- Rat (Acute)
- 2.28
- Rat (Chronic Oral)
- 2.48
- Fathead Minnow
- 4.38
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 358.47
- Hydration Free Energy
- -9.91
- Log(D) at pH=7.4
- 2.28
- Log(P)
- 3.42
- Log S
- -3.97
- Log(Vapor Pressure)
- -6.03
- Melting Point
- 129.4
- pKa Acid
- 5.76
- pKa Basic
- 3.71
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8514 |
| Snake venom metalloproteinase atrolysin-D | P15167 | VM1AD_CROAT | Crotalus atrox | 3 | 0.8414 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8384 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 3 | 0.8210 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8147 |
| Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial | Q33862 | Q33862_ASCSU | Ascaris suum | 3 | 0.8039 |
| Biflaviolin synthase CYP158A2 | Q9FCA6 | C1582_STRCO | Streptomyces coelicolor / M145) | 3 | 0.8009 |
| ActVA 6 protein | Q53908 | Q53908_STRCH | Streptomyces coelicolor | 3 | 0.7944 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7928 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7881 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7520 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.7451 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 2 | 0.7430 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 2 | 0.7412 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.7404 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7397 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 2 | 0.7361 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7324 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7273 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7236 |
| Anthranilate phosphoribosyltransferase | P50384 | TRPD_SACS2 | Saccharolobus solfataricus | 2 | 0.7182 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7163 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7160 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7091 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7064 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7057 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.7037 |
| 3-ketosteroid dehydrogenase | Q9RA02 | Q9RA02_RHOER | Rhodococcus erythropolis | 2 | 0.7036 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7019 |