1,2-dihydroxy-3-methoxyxanthone - Compound Card

1,2-dihydroxy-3-methoxyxanthone

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1,2-dihydroxy-3-methoxyxanthone

Structure
Zoomed Structure
  • Family: Plantae - Sapotaceae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles COc1cc2oc3c(O)cccc3c(=O)c2c(c1O)O
InChI InChI=1S/C14H10O6/c1-19-9-5-8-10(13(18)12(9)17)11(16)6-3-2-4-7(15)14(6)20-8/h2-5,15,17-18H,1H3
InChIKey WTNKEMMCIMLVND-UHFFFAOYSA-N
Formula C14H10O6
HBA 6
HBD 3
MW 274.23
Rotatable Bonds 1
TPSA 100.13
LogP 2.07
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.07
Exact Mass 274.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Manilkara obovata Sapotaceae Plantae 362719

Showing of synonyms

  • Akosung E, Kenmogne SB, et al. (2021). Bioactive constituents from Manilkara obovata (Sabine & G.Don) J.H.Hemsl.. Natural product research,2021, 35(22), 4347-4356. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 274.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.910
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
73.1
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
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
6.850
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.460
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.360
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.860
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
4.710
Rat (Acute)
2.190
Rat (Chronic Oral)
3.080
Fathead Minnow
4.240
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
429.100
Hydration Free Energy
-11.660
Log(D) at pH=7.4
1.810
Log(P)
2.15
Log S
-4.47
Log(Vapor Pressure)
-6.86
Melting Point
219.29
pKa Acid
4.81
pKa Basic
4.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9423
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9240
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9239
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9217
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9140
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.9082
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9028
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8939
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8908
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8824
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8751
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8746
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8710
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.8658
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8639
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8546
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8529
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8503
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8457
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8397
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8342
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8287
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8286
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.8255
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8250
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.8236
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.8218
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8169
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.8124
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8092
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8073
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8045
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8031
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8022
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7986
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 5 0.7985
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7982
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7936
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7914
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.7911
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7908
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7902
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7887
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7837
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7807
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7779
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7718
Deoxyribodipyrimidine photo-lyase Q8PYK9 Q8PYK9_METMA Methanosarcina mazei 5 0.7717
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7715
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7681
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7668
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7651
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7645
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7628
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7622
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7618
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7607
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7605
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7593
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7574
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7552
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7544
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7532
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7497
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7496
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7492
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7491
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7491
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7489
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7482
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7475
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7464
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7461
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7454
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7446
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7443
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7442
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7440
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7434
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7425
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7421
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7414
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7407
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7403
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7398
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7381
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7369
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7368
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7367
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7364
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7363
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7361
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7334
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7331
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7317
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7313
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7306
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7302
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7301
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7300
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7287
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7287
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7280
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7274
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7267
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7266
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7262
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7257
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7250
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7239
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7236
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7233
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7226
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7210
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7210
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7196
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7188
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7172
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7165
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7164
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7157
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7156
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7149
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7147
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7136
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7117
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7100
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7095
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7086
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7085
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7078
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7069
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 4 0.7060
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7057
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7040
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7020
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7020
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7012

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