5,8-dihydroxy-3-methoxy-2-methylnaphthalene-1,4-dione - Compound Card

5,8-dihydroxy-3-methoxy-2-methylnaphthalene-1,4-dione

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5,8-dihydroxy-3-methoxy-2-methylnaphthalene-1,4-dione

Structure
Zoomed Structure
  • Family: Plantae - Asphodelaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Naphthoquinone
Canonical Smiles COC1=C(C)C(=O)c2c(C1=O)c(O)ccc2O
InChI InChI=1S/C12H10O5/c1-5-10(15)8-6(13)3-4-7(14)9(8)11(16)12(5)17-2/h3-4,13-14H,1-2H3
InChIKey OFWDPOZCVBLOIH-UHFFFAOYSA-N
Formula C12H10O5
HBA 5
HBD 2
MW 234.21
Rotatable Bonds 1
TPSA 83.83
LogP 1.4
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 234.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aloe dawei Asphodelaceae Plantae 1331517
2 Aloe secundiflora Asphodelaceae Plantae 1593107

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]
  • Induli M, Cheloti M, et al. (2012). Naphthoquinones from the roots of Aloe secundiflora. Phytochemistry Letters,2012,5(3),506-509. [View] [PubMed]
Pubchem: 171989807

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 234.21 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.580
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.530
Plasma Protein Binding
27.76
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
9.170
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.510
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.020
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.140
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
4.810
Rat (Acute)
2.760
Rat (Chronic Oral)
3.100
Fathead Minnow
4.040
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
368.220
Hydration Free Energy
-10.030
Log(D) at pH=7.4
1.900
Log(P)
2.45
Log S
-3.92
Log(Vapor Pressure)
-5.08
Melting Point
172.23
pKa Acid
6.29
pKa Basic
4.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9547
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9547
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9537
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9537
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9483
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9483
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8990
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8990
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8849
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8849
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8608
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8608
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8506
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8506
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8497
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8497
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8403
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8403
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 4 0.8319
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 4 0.8319
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8272
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8272
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8248
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8248
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8110
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8110
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.8092
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.8092
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7879
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7879
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7690
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7690
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7657
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7657
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7508
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7508
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7471
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7471
Thymidylate synthase P07607 TYSY_MOUSE Mus musculus 4 0.7444
Thymidylate synthase P07607 TYSY_MOUSE Mus musculus 4 0.7444
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7424
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7424
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 3 0.7382
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 3 0.7382
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7325
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7325
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7302
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7302
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7274
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7274
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7270
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7270
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7223
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7223
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7182
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7182
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7146
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7146
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7128
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7128
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7091
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7091
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7039
Glycogenin-1 P46976 GLYG_HUMAN Homo sapiens 3 0.7039
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7032
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7032
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7025
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7025
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 3 0.7010
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 3 0.7010
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7003
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7003

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