3′-hydroxymethyl-2′-(4′′-hydroxy-3′′,5′′-dimethoxyphenyl)-5′,6′:5,6-(6,8-dihydroxyxanthone)-1′,4′-dioxane - Compound Card

3′-hydroxymethyl-2′-(4′′-hydroxy-3′′,5′′-dimethoxyphenyl)-5′,6′:5,6-(6,8-dihydroxyxanthone)-1′,4′-dioxane

Select a section from the left sidebar

3′-hydroxymethyl-2′-(4′′-hydroxy-3′′,5′′-dimethoxyphenyl)-5′,6′:5,6-(6,8-dihydroxyxanthone)-1′,4′-dioxane

Structure
Zoomed Structure
  • Family: Guttiferae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles OCC1Oc2c(OC1c1cc(OC)c(c(c1)OC)O)ccc1c2oc2cc(O)cc(c2c1=O)O
InChI InChI=1S/C24H20O10/c1-30-16-5-10(6-17(31-2)21(16)29)22-18(9-25)34-24-14(32-22)4-3-12-20(28)19-13(27)7-11(26)8-15(19)33-23(12)24/h3-8,18,22,25-27,29H,9H2,1-2H3
InChIKey ZIXRDOIIRHBBIP-UHFFFAOYSA-N
Formula C24H20O10
HBA 10
HBD 4
MW 468.41
Rotatable Bonds 4
TPSA 148.05
LogP 2.95
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 468.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum roeperianum Guttiferae Plantae —

Showing of synonyms

  • Guefack MF, Damen F, et al. (2020). Cytotoxic Constituents of the Bark of Hypericum roeperianum towards Multidrug-Resistant Cancer Cells.. Evidence-based complementary and alternative medicine : eCAM,2020, 2020, 4314807. [View] [PubMed]
Pubchem: 14427464

No compound-protein relationship available.

Structure

SMILES: c1cccc(c2=O)c1oc(c23)c4c(cc3)OC(CO4)c5ccccc5

Level: 1

Mol. Weight: 330.34 g/mol

Structure

SMILES: O1CCOc(cc2)c1c(c23)oc4c(c3=O)cccc4

Level: 0

Mol. Weight: 254.24 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.87
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.02
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.35
Plasma Protein Binding
59.57
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.85
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.0
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.94
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
-288.15
Rat (Acute)
2.22
Rat (Chronic Oral)
3.17
Fathead Minnow
5.76
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
579.43
Hydration Free Energy
-2.99
Log(D) at pH=7.4
2.31
Log(P)
2.63
Log S
-6.11
Log(Vapor Pressure)
-9.92
Melting Point
237.82
pKa Acid
6.94
pKa Basic
2.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9824
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9280
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9245
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9186
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9103
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9070
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9021
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8820
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8704
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8656
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8607
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8582
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8578
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8555
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8552
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8515
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8492
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8454
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8452
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8451
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.8387
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.8355
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8313
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8311
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8306
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8229
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8131
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8080
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8070
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8044
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8014
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7947
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.7937
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7931
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7929
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7858
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.7825
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7816
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7783
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7773
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7773
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7744
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7741
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7730
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7726
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7723
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7715
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7709
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.7697
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7696
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7674
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7662
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7640
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7608
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7583
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7573
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7568
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7561
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7550
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7546
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7545
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7531
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7525
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7520
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7513
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7511
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7468
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7437
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7432
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7432
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7416
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7405
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7404
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 4 0.7395
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7366
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7354
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7322
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7310
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7287
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7283
L-lactate dehydrogenase Q5SJA1 LDH_THET8 Thermus thermophilus 3 0.7270
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7268
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7260
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7260
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7245
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7240
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7237
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7230
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7229
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 4 0.7229
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7215
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7214
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7197
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7196
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7194
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7187
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 4 0.7173
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7167
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 4 0.7143
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7143
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7128
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7111
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7106
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7090
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7082
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7075
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7070
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7065
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7064
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7061
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7052
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7044
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7041
Maltokinase A1TH50 MAK_MYCVP Mycolicibacterium vanbaalenii 3 0.7030
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7028
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7028
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7020
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7006
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7004
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7004

Download SDF