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Substance Name: Lapachol
RN: 84-79-7
UNII: B221938VB6
InChIKey: CIEYTVIYYGTCCI-UHFFFAOYSA-N

Molecular Formula

  • C15-H14-O3

Molecular Weight

  • 242.2726
 

Classification Codes

  • Anthelmintics
  • Anti-Infective Agents
  • Antifungal Agents
  • Antimalarials
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Antiviral Agents
  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Lapachol

Synonyms

  • 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione
  • 2-Hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone
  • 4-08-00-02487 (Beilstein Handbook Reference)
  • Bethabarra wood
  • BRN 2051889
  • C.I. 75490
  • C.I. Natural Yellow 16
  • CCRIS 745
  • EINECS 201-563-7
  • Greenharten
  • Greenhartin
  • IPE-tobacco wood
  • Lapachic acid
  • Lapachol
  • Lapachol wood
  • NSC 11905
  • NSC 629756
  • NSC-11905
  • Surinam greenheart wood
  • Taigu wood
  • Taiguic acid
  • Tecomin
  • Tecomin (VAN)
  • UNII-B221938VB6
  • Zlut prirodni 16
  • Zlut prirodni 16 [Czech]

Systematic Names

  • 1,4-Naphthalenedione, 2-hydroxy-3-(3-methyl-2-butenyl)- (9CI)
  • 1,4-Naphthoquinone, 2-hydroxy-3-(3-methyl-2-butenyl)-
  • 2-Hydroxy-3-(3-methylbut-2-enyl)-1,4-naphthoquinone
  • Lapachol

Registry Numbers

CAS Registry Number

  • 84-79-7

FDA UNII

  • B221938VB6

System Generated Number

  • 0000084797

Structure Descriptors

InChI

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

InChIKey

CIEYTVIYYGTCCI-UHFFFAOYSA-N

Smiles

CC(=CCC1=C(C(=O)c2ccccc2C1=O)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   Journal of Medicinal Chemistry. Vol. 26, Pg. 570, 1983.
mouse LD50 oral 487mg/kg (487mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Toxicology and Applied Pharmacology. Vol. 17, Pg. 1, 1970.
rat LDLo oral 1200mg/kg (1200mg/kg)   Toxicology and Applied Pharmacology. Vol. 17, Pg. 1, 1970.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 139.5 deg C   EXP
log P (octanol-water) 3.130 (none)   EST
Atmospheric OH Rate Constant 1.02E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.