6,7-dimethoxy xanthopurpurin - Compound Card

6,7-dimethoxy xanthopurpurin

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6,7-dimethoxy xanthopurpurin

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles COc1cc2c(cc1OC)C(=O)c1c(C2=O)c(O)cc(c1)O
InChI InChI=1S/C16H12O6/c1-21-12-5-8-9(6-13(12)22-2)16(20)14-10(15(8)19)3-7(17)4-11(14)18/h3-6,17-18H,1-2H3
InChIKey XNGTZVMLKRWTFR-UHFFFAOYSA-N
Formula C16H12O6
HBA 6
HBD 2
MW 300.27
Rotatable Bonds 2
TPSA 93.06
LogP 1.89
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: 10402511
Nmrshiftdb2: 70092140

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)
-4.44
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.740
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
63.86
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.130
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.840
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.150
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.570
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
4.530
Rat (Acute)
2.240
Rat (Chronic Oral)
2.920
Fathead Minnow
4.470
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
440.120
Hydration Free Energy
-10.380
Log(D) at pH=7.4
2.630
Log(P)
2.79
Log S
-6.84
Log(Vapor Pressure)
-7.03
Melting Point
236.0
pKa Acid
6.78
pKa Basic
3.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9379
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9313
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9204
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9150
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.9061
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8998
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8969
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8930
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8929
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8911
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8900
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8853
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8824
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8792
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8702
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8624
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8534
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8513
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8454
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8448
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8421
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8414
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8377
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8355
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8350
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8325
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.8279
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8236
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8202
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8166
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.8158
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8148
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8139
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8126
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8108
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8059
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8038
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.8034
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8023
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8007
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7968
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7946
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7915
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7850
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7844
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7811
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7810
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7784
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7771
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7747
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7719
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7713
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7700
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.7700
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7669
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7639
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7637
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7606
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7575
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7565
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7529
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7507
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7498
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7488
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7479
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7467
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7459
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7457
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7446
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7433
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7428
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7417
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7398
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.7395
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7356
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7352
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7348
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7333
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7326
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7284
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7278
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7270
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7266
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7265
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7247
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7239
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7227
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7214
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7210
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7178
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7171
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7171
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7153
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7145
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7137
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7125
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7115
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7103
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7102
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7094
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7078
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7072
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7067
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7040
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7037
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7029

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