6-hydroxy-7-methoxy rubiadin - Compound Card

6-hydroxy-7-methoxy rubiadin

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6-hydroxy-7-methoxy rubiadin

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1cc2c(cc1O)C(=O)c1c(C2=O)c(O)c(c(c1)O)C
InChI InChI=1S/C16H12O6/c1-6-10(17)4-9-13(14(6)19)16(21)8-5-12(22-2)11(18)3-7(8)15(9)20/h3-5,17-19H,1-2H3
InChIKey DLVVMUVQNGZWEA-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 3
MW 300.27
Rotatable Bonds 1
TPSA 104.06
LogP 1.9
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 300.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Galium sinaicum Rubiaceae Plantae 25168

Showing of synonyms

  • El-Gamal A.A, Takeya K, et al. (1996). Anthraquinones from the polar fractions of Galium sinaicum. Phytochemistry, 1996, 42(4), 1149-55. [View] [PubMed]
Pubchem: 10732948
Nmrshiftdb2: 70092137

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 300.27 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.870
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.880
Plasma Protein Binding
65.21
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.690
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.430
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.380
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.990
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.680
Rat (Acute)
2.460
Rat (Chronic Oral)
3.120
Fathead Minnow
4.280
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
449.290
Hydration Free Energy
-9.780
Log(D) at pH=7.4
2.410
Log(P)
3.4
Log S
-6.55
Log(Vapor Pressure)
-7.22
Melting Point
266.16
pKa Acid
5.21
pKa Basic
5.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9493
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.9196
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8887
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8884
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8878
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8843
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8833
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8772
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8723
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8614
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.8611
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8588
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8549
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8537
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8509
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8425
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8400
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8390
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8339
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8195
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8178
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8149
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8134
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8108
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8087
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8066
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8061
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8053
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8016
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8006
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7997
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7981
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7967
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7961
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7915
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7881
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7874
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7826
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7825
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7790
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7765
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7754
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7735
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7725
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7716
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7700
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7680
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7667
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7664
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7659
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7641
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7608
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7596
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7579
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7561
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7537
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7504
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7480
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7471
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7457
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7435
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7428
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7402
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7393
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7392
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7375
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7342
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7328
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7326
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7284
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7258
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7253
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7248
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7237
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7232
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7198
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7190
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7186
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7180
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7178
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7140
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7130
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7129
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7129
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7124
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7119
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7111
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7102
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7100
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7093
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7088
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7085
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7041
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7036
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7032
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7028

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