6-hydroxy-3,5-dimethoxy-2-methyl-1,4-naphthoquinone - Compound Card

6-hydroxy-3,5-dimethoxy-2-methyl-1,4-naphthoquinone

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6-hydroxy-3,5-dimethoxy-2-methyl-1,4-naphthoquinone

Structure
Zoomed Structure
  • Family: Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Naphthoquinone
Canonical Smiles COC1=C(C)C(=O)c2c(C1=O)c(OC)c(cc2)O
InChI InChI=1S/C13H12O5/c1-6-10(15)7-4-5-8(14)13(18-3)9(7)11(16)12(6)17-2/h4-5,14H,1-3H3
InChIKey AEOQWSVOFKWWKC-UHFFFAOYSA-N
Formula C13H12O5
HBA 5
HBD 1
MW 248.23
Rotatable Bonds 2
TPSA 72.83
LogP 1.7
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 248.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe dawei Asphodelaceae Plantae 1331517

Showing of synonyms

  • Abdissa N, Induli M, et al. (2014). Cytotoxic quinones from the roots of Aloe dawei. Molecules,2014,19(3),3264-3273. [View] [PubMed]
Pubchem: 102233555

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)C=CC2=O

Level: 0

Mol. Weight: 158.16 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.47
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.520
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.640
Plasma Protein Binding
24.35
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
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.420
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.880
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.480
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.500
Micronucleos
Toxic
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
4.410
Rat (Acute)
2.410
Rat (Chronic Oral)
2.780
Fathead Minnow
4.240
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
362.810
Hydration Free Energy
-8.230
Log(D) at pH=7.4
1.580
Log(P)
2.0
Log S
-3.46
Log(Vapor Pressure)
-4.93
Melting Point
179.74
pKa Acid
5.55
pKa Basic
3.58
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 0.9220
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9220
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9141
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9141
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9121
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9121
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8624
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8624
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8571
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8571
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8335
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8335
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 3 0.8081
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 3 0.8081
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7982
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7982
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7742
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7742
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7691
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7691
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7540
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7540
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7481
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7481
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7445
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7445
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7413
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7413
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7405
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7405
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7361
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7361
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7353
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7353
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7333
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7333
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7318
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7318
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7294
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7294
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7288
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7288
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7247
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7247
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7237
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7237
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7227
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7227
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7223
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7223
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7141
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7141
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7101
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7101
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7081
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7081
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7071
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7071
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7067
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7067
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7012
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7012

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