6-hydroxyxanthopurpurin - Compound Card

6-hydroxyxanthopurpurin

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6-hydroxyxanthopurpurin

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Anthraquinone
Canonical Smiles Oc1ccc2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)O
InChI InChI=1S/C14H8O5/c15-6-1-2-8-9(3-6)13(18)10-4-7(16)5-11(17)12(10)14(8)19/h1-5,15-17H
InChIKey HTGYRSWFBJFKRE-UHFFFAOYSA-N
Formula C14H8O5
HBA 5
HBD 3
MW 256.21
Rotatable Bonds 0
TPSA 94.83
LogP 1.58
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 256.04
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. (1992). Anthraquinones from Galium sinaicum. Phytochemistry, 1992, 31(1), 355-360. [View]
Pubchem: 9992552

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 256.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
66.3
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
8.520
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.010
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.880
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.890
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.640
Rat (Acute)
2.390
Rat (Chronic Oral)
3.240
Fathead Minnow
4.090
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
441.370
Hydration Free Energy
-11.050
Log(D) at pH=7.4
1.730
Log(P)
2.75
Log S
-5.69
Log(Vapor Pressure)
-7.61
Melting Point
312.32
pKa Acid
7.07
pKa Basic
6.17
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 0.9386
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9245
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9097
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.9073
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9012
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8979
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8973
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8957
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.8939
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8903
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8876
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8849
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8840
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8840
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8839
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8818
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.8685
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.8684
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8643
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8637
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8611
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8554
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8551
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8446
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8445
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8403
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.8385
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8385
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8378
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8377
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8364
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8357
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8351
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.8339
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8330
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8327
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.8286
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8264
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8257
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8255
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.8216
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8208
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8181
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8163
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8102
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8084
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8070
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8013
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8006
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7983
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7948
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7928
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7922
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7916
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 4 0.7904
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7893
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7874
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7863
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7851
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7847
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7841
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7829
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7827
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7800
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7793
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7784
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7764
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7763
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7760
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7753
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7708
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7702
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7672
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7666
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7645
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7632
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7603
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7578
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7571
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7570
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7529
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7511
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7482
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7479
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7478
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7451
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 4 0.7440
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7434
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7415
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7400
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7395
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7383
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7378
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7362
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7354
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7351
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7347
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7332
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7330
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7315
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7291
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7285
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7266
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7259
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7253
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7251
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7250
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 4 0.7244
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7229
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7213
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7210
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7208
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7200
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7190
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7140
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7137
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7130
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7130
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7120
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7115
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7110
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7105
Granule-bound starch synthase 1, chloroplastic/amyloplastic Q0DEV5 SSG1_ORYSJ Oryza sativa subsp. japonica 3 0.7061
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7058
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7053
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7046
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7045
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7035
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7013
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7010

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