1,5-dihydroxy-3-methoxy-7-methylanthraquinone - Compound Card

1,5-dihydroxy-3-methoxy-7-methylanthraquinone

Select a section from the left sidebar

1,5-dihydroxy-3-methoxy-7-methylanthraquinone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Anthraquinone
Canonical Smiles COc1cc(O)c2c(c1)C(=O)c1c(C2=O)cc(cc1O)C
InChI InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)10-5-8(21-2)6-12(18)14(10)15(9)19/h3-6,17-18H,1-2H3
InChIKey LLZYZGMVXFGQAY-UHFFFAOYSA-N
Formula C16H12O5
HBA 5
HBD 2
MW 284.27
Rotatable Bonds 1
TPSA 83.83
LogP 2.19
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 284.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cassia obtusifolia Leguminosae/Fabaceae Plantae 346985

Showing of synonyms

  • Sob S, Wabo H, et al. (2010). Anthraquinones, sterols, triterpenoids and xanthones from Cassia obtusifolia. Biochemical Systematics and Ecology, 2010, 38(3), 342-345. [View]
Pubchem: 15138599
Nmrshiftdb2: 60076496

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 284.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.610
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.910
Plasma Protein Binding
59.79
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
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.620
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.260
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.010
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.350
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
4.840
Rat (Acute)
2.360
Rat (Chronic Oral)
2.940
Fathead Minnow
4.420
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
423.650
Hydration Free Energy
-8.540
Log(D) at pH=7.4
2.960
Log(P)
3.91
Log S
-6.86
Log(Vapor Pressure)
-7.12
Melting Point
218.58
pKa Acid
7.67
pKa Basic
4.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9517
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9395
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9345
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9144
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9097
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9096
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8931
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8886
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8850
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8846
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8839
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8725
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8637
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.8635
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8552
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8545
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8490
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8288
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8275
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8275
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.8052
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8012
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8010
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8009
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7972
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7967
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7960
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7959
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7937
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7926
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7914
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7905
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7895
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7820
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7794
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7780
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7757
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7749
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7732
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7727
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7713
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7665
Fructose-1,6-bisphosphatase 1 P00636 F16P1_PIG Sus scrofa 3 0.7621
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7588
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7583
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7565
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7555
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7550
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7548
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7542
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7541
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7474
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7473
Tyrosine-protein kinase Lyn P25911 LYN_MOUSE Mus musculus 4 0.7460
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7439
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7426
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7419
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7368
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7361
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7347
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7326
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7290
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7272
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7255
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7235
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7234
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7222
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7218
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7214
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7205
5,6-dimethylbenzimidazole synthase Q92PC8 BLUB_RHIME Rhizobium meliloti 5 0.7198
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7179
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 4 0.7170
Bifunctional dihydrofolate reductase-thymidylate synthase Q27783 DRTS_TRYBB Trypanosoma brucei brucei 4 0.7167
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7156
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7150
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7139
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7101
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7101
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7094
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7094
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7089
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7080
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7079
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7060
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7057
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7054
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7044
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7043
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7032
GTPase IMAP family member 2 Q9UG22 GIMA2_HUMAN Homo sapiens 3 0.7028
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7026

Download SDF