5,8-dihydroxy-2-methylanthraquinone - Compound Card

5,8-dihydroxy-2-methylanthraquinone

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5,8-dihydroxy-2-methylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Verbenaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles Cc1ccc2c(c1)C(=O)c1c(C2=O)c(O)ccc1O
InChI InChI=1S/C15H10O4/c1-7-2-3-8-9(6-7)15(19)13-11(17)5-4-10(16)12(13)14(8)18/h2-6,16-17H,1H3
InChIKey JKVKLDWULQJCIS-UHFFFAOYSA-N
Formula C15H10O4
HBA 4
HBD 2
MW 254.24
Rotatable Bonds 0
TPSA 74.6
LogP 2.18
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 254.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tectona grandis Verbenaceae Plantae 41396
2 Tectona grandis Verbenaceae Plantae 41396

Showing of synonyms

  • Bitchagno GT, Sama Fonkeng L, et al. (2015). Antibacterial activity of ethanolic extract and compounds from fruits of Tectona grandis (Verbenaceae).. BMC complementary and alternative medicine,2015, 15, 265. [View] [PubMed]
  • Kopa T, Tchinda A, et al. (2014). Antiplasmodial anthraquinones and hemisynthetic derivatives from the leaves of Tectona grandis (Verbenaceae). Phytochemistry Letters, 2014, 8, 41-45. [View]
Pubchem: 11230545

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 254.24 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.98

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
61.53
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.28
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.53
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
4.79
Rat (Acute)
2.5
Rat (Chronic Oral)
2.97
Fathead Minnow
4.27
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
409.72
Hydration Free Energy
-9.67
Log(D) at pH=7.4
2.7
Log(P)
3.81
Log S
-6.15
Log(Vapor Pressure)
-7.54
Melting Point
209.97
pKa Acid
5.73
pKa Basic
5.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9455
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9406
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9305
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9286
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8824
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8820
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8707
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8699
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8521
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8457
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8448
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8326
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8269
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8236
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.8220
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8219
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8206
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8186
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8147
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8086
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8058
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8052
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8019
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8017
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8001
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7898
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7772
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7721
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7688
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7687
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7675
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7661
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7660
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 4 0.7640
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7639
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7637
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7607
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7595
Aurora kinase B-A Q6DE08 AUKBA_XENLA Xenopus laevis 3 0.7586
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7583
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7559
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7494
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7458
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7447
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7429
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7422
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7415
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7409
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7406
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7400
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 4 0.7395
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 5 0.7392
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7384
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7370
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7341
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7327
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7325
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7310
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 4 0.7310
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7304
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7300
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7292
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7280
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7262
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7254
Serine/threonine-protein kinase TBK1 Q9UHD2 TBK1_HUMAN Homo sapiens 3 0.7249
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7247
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7244
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7236
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7232
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7225
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7214
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7212
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 4 0.7207
2-Hydroxyacid oxidase 1 Q9UJM8 HAOX1_HUMAN Homo sapiens 3 0.7180
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7175
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7172
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7143
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7139
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7134
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7128
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7119
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7119
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7111
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7102
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7096
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7059
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7056
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7048
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7042
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7032
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7020
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7004
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7003

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