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(+)-lariciresinol +   
(+)-lyoniresinol-3-alpha-O-beta-D-glucopyranoside 
(-)-rotiorin 
(10E,15Z)-9,12,13-trihydroxy-10,15-octadecadienoic acid 
(1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one 
(2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propanoic acid 
(3R,4R)-(-)-6-methoxy-1-oxo-3-n-pentyl-3,4-dihydro-1H-isochromen-4-yl-acetate 
(9Z)-heptadecenoic acid +  
(E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec-8-ene-1,3-dione 
(E)-cinnamaldehyde +   
(E)-oct-2-enal 
(E)-sinapaldehyde +  
(R)-3-hydroxybutanenitrile 
(R)-7-butyl-6,8-dihydroxy-3-[(3E)-pent-3-en-1-yl]-3,4-dihydroisochromen-1-one 
1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione 
13-epi-manool 
2,3-dihydrobiochanin A 
2,4-diacetylphloroglucinol 
2,4-diacetylphloroglucinol(1-) 
2,6,7-trihydroxy-3-methylnaphthalene-1,4-dione 
2,8-dihydroxy-1,4-naphthoquinone 
2-(4-hydroxyphenyl)ethanol +   
2-hydroxy-3-(2-hydroxyethyl)naphthalene-1,4-dione 
2-O,3-dimethylflaviolin 
2-phenylethyl 1H-indol-3-ylacetate 
3-acetylbenzamide 
3-linalylflaviolin 
3-phenylpropionic acid +   
4-(2,4,7-trioxa-bicyclo[4.1.0]heptan-3-yl)phenol 
4-hydroxymellein 
5,6-dehydrotomatine 
5-(undeca-3,5,7-trien-1-yl)-2-furyl hydrogen carbonate 
5-(undeca-3,5,7-trien-1-yl)furan-2-ol +  
5-bromo-8-methoxy-1-methyl-beta-carboline 
5-chloro-7-iodoquinolin-8-ol  
5-hydroxy-8-methoxy-4-phenylisoquinolin-1(2H)-one 
5-hydroxybenzofuran-2-one 
5-O-demethylpaxanthonin +  
5alpha-ergosta-7,22-dien-3beta-ol 
6-linalyl-2-O,3-dimethylflaviolin 
6-tuliposide B 
7-O-geranyl-2-O,3-dimethylflaviolin 
8-acetoxyheterophyllisine 
9-deoxy-hymatoxin A 
Acetylshikonin 
acrylonitrile +   
actinodaphnine 
aculeacin A 
aigialone 
aliphatic nitrogen antifungal agent +  
Alkannin  
Alkannin beta,beta-dimethylacrylate 
altenusin  
ambiguine H 
ambiguine I 
amide antifungal agent +   
amphotericin B methyl ester  
antibiotic antifungal agent +   
antidote +   
antifungal drug +   
antimycin A  
Aristolindiquinone 
arjunolic acid +   
ascomycin  
asperentin +   
asphodelin A +  
asphodelin A-4'-O-beta-glucoside 
asukamycin 
atovaquone  
aureoquinone 
aureothin 
australifungin 
azaserine 
azoxybacilin 
bacilysocin 
BAR0329 
bauhinoxepin F 
bauhinoxepin I 
bauhinoxepin J 
beauvericin  
benfotiamine  
benzethonium chloride  
beta,beta-Dimethylacrylshikonin 
beta-thujaplicin  
bikaverin 
borax 
borrelidin  
botanical anti-fungal agent +   
botrallin 
botryosphaerin H 
brasilinolide A 
brasilinolide B 
bridged diphenyl antifungal agent +   
bromophycolide A 
butin +  
CAF-603 
callipeltin A 
cardioprotective agent +   
casbene 
cercosporamide 
cerulenin  
chaetoglobosin L 
chaetoviridin A 
chaetoviridin B 
chamaejasmenin A 
chamaejasmenin D 
chlorflavonin 
cis-trans-nepetalactone 
citrafungin A 
citrafungin B 
citronellal +   
CJ-01 
conazole antifungal agent +   
concanamycin A  
coniferyl aldehyde +   
cordycepin triphosphate 
crystal violet  
crystal violet cation +   
CT2108A 
CT2108B 
CTBT 
curcumin +   
cyclomulberrin +  
cyclosporin A +   
cystothiazole A 
danielone 
decanal  
deferiprone  
Deoxyshikonin 
deoxyviolacein 
dequalinium +   
dequalinium chloride 
diallyl disulfide  
dicarboximide antifungal agent +   
dichlorodiaportinolide 
dichlorvos  
diethylstilbestrol +   
dihydrosanguinarine +   
dihydroxyacetone +   
dioncophylline A 
dioscin  
Diospyrin 
djalonensone 
drilodefensin 1 
Droserone 
Echinone 
elaiophylin 
enfumafungin 
epi-isochromophilone II 
epichlicin 
ethylparaben  
eugeniin 
eurysterol A 
eurysterol A sulfonic acid 
eurysterol B 
eurysterol B sulfonic acid 
exalamide 
fellutamide C 
fellutamide D 
ferruginol +  
feruloylagmatine +  
flaviolin +  
fomepizole  
FR171456 
FR207944 
FR901469 
FR901469 hydrochloride 
fungicide +   
furanocandin 
fusaripeptide A 
fusarithioamide A 
gepinacin 
geranic acid  
gliotoxin  
glomosporin 
Gly-Gln 
glyceollin III 
GM 193663 
guignardone N 
hamacanthin A +  
helvolic acid methyl ester 
hepatoprotective agent +   
heptachlor  
hypocrellin D 
hypothemycin 
hypothiocyanous acid 
Hypoxylone 
imidazole antifungal agent +   
impatienol 
isatinone A 
isatinone B 
isavuconazonium +  
isoaigialone B 
isoalantolactone  
isoamylol +   
Isobutylshikonin 
isochamaejasmenin B 
juglone  
kaempferol 3-O-beta-D-galactoside  
L-citrulline +  
Lapachol  
lawsone  
1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis.
leptomycin A 
leptomycin B  
leucascandrolide A congener 
liriodenine 
lubimin +  
mediomycin A 
mediomycin B 
methoxyacrylate strobilurin antifungal agent +   
methoxycarbanilate strobilurin antifungal agent +  
methoxyiminoacetamide strobilurin antifungal agent +  
methoxyiminoacetate strobilurin antifungal agent +   
methyl nonanoate 
methylisothiazolinone +   
methylparaben  
mevastatin +   
miconazole nitrate 
miltefosine  
monensin A  
monodansylcadaverine  
monotesone A 
morpholine antifungal agent +   
mucidin 
multiplolide A 
multiplolide B 
myriocin  
N-[5-(1-naphthylmethyl)-1,3-thiazol-2-yl]cyclohexanecarboxamide 
N-benzyl-N-methyl-2-(3-oxo-1,2-benzothiazol-2-yl)acetamide 
N-carbamoyl-L-cysteine 
N-octylhomovanillamide 
naled  
naphthazarin  
neothyonidioside 
nephroprotective agent +   
neuroprotective agent +   
nigerone 
nikkomycin Z 
nitroxoline  
NK154183A 
NK154183B 
NK372135A 
NK372135B 
NK372135C 
nocardione A 
NP-101A 
oceanalin A 
oltipraz  
osthenol 
oxolinic acid 
oxybenzone  
paclobutrazol  
pallidol  
palmariol B 
palmarumycin C8 
papulacandin A 
papulacandin B 
papulacandin C 
papulacandin D 
parathion-methyl  
pentamidine  
PF 1163A 
PF 1163B 
phenazine-1-carboxylic acid  
phenylephrine  
phleomycin D1 +  
phomalevone B 
phosphatoquinone B 
physcion +   
phytocassane +  
pinocembrin chalcone 
plakortide F free acid 
plumbagin  
pneumocandin B0 +   
polyhexamethylene biguanide 
polyhexamethylene biguanide hydrochloride 
polysulfur  
pomecin A 
pradimicin +  
prop-2-yn-1-ol +   
propylparaben  
protobassic acid +  
purpurogallin  
pyrimidine antifungal agent +   
radiation protective agent +   
radicicol  
Ramentaceone 
rhinacanthin C 
rhinacanthin D 
rhizopycnolide A 
rifamycin-undecaketide carboxylic acid +  
rotiorinol A 
rotiorinol C 
rubrorotiorin 
salicylic acid +   
salzmannianoside A 
salzmannianoside B 
scalusamide A 
sch 54445 
sch 725432 
sclareol 
sclerodol B 
selinone 
Shikonin  
sinefungin  
sodium arsenite  
solasodine  
solasodine(1+) +  
sordaricin 
sordarin +  
sorocenol H 
sporothriolide 
stemphyperylenol 
sterol demethylation inhibitor +   
stichloroside C1 
streptoverticillin 
strobilurin antifungal agent +   
strobilurin B 
surfactin  
surfactin A +   
surfactin B +   
surfactin C +   
surfactin D +   
syringomycin E 
talosin A 
talosin B 
tavaborole 
tea tree oil  
teduglutide 
theopalauamide 
thiadiazole antifungal agent +  
tianshic acid 
tolfenpyrad 
tolybyssidin A 
tolybyssidin B 
tomatine +  
trans-2,3-epoxydeca-4,6,8-triyn-1-ol 
trans-cis-nepetalactone 
triazole antifungal agent +   
tributyrin  
trichodermin 
Tricrozarin A 
tulipalin B 
UK-2A 
UK-2B 
UK-3A 
undecanoic acid +   
usnic acid +   
vamidothion 
venturicidin 
veratraldehyde 
violacein  
wighteone 
yanuthone D 
yanuthone K +  
yanuthone L 
yanuthone M 
yanuthone X2 +  
YM-47522 
Ys-II 
Ys-IV 
yuccalan 
zonisamide  

Synonyms
Related Synonyms: 2-HYDROXYNAPHTHOQUINONE ;   2-hydroxy-1,4-naphthalenedione ;   2-hydroxy-1,4-naphthoquinone ;   2-hydroxynaphthalene-1,4-dione ;   Formula=C10H6O3 ;   Henna ;   InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H ;   InChIKey=CSFWPUWCSPOLJW-UHFFFAOYSA-N ;   SMILES=OC1=CC(=O)c2ccccc2C1=O
Alternate IDs: CHEBI:44399 ;   CHEBI:6395
Xrefs: Beilstein:1565260 ;   CAS:83-72-7 ;   Gmelin:4828 ;   KEGG:C10368 ;   KNApSAcK:C00002837
Xref Mesh: MESH:C005090
Xrefs: PDBeChem:NQ
Cyclic Relationships: is_tautomer_of CHEBI:93166

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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.