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

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

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

Structure
Zoomed Structure
  • Family: Guttiferae
  • Kingdom: Plantae
  • Class: Xanthone
Canonical Smiles OCC1Oc2c(OC1c1cc(OC)c(c(c1)OC)O)ccc1c2oc2ccccc2c1=O
InChI InChI=1S/C24H20O8/c1-28-17-9-12(10-18(29-2)21(17)27)22-19(11-25)32-24-16(31-22)8-7-14-20(26)13-5-3-4-6-15(13)30-23(14)24/h3-10,19,22,25,27H,11H2,1-2H3
InChIKey BKTSQHMLXIDWQT-UHFFFAOYSA-N
Formula C24H20O8
HBA 8
HBD 2
MW 436.42
Rotatable Bonds 4
TPSA 107.59
LogP 3.54
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 436.12
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]

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)
-4.93
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.64
Plasma Protein Binding
63.62
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.7
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
-141.95
Rat (Acute)
2.27
Rat (Chronic Oral)
2.57
Fathead Minnow
5.74
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
526.04
Hydration Free Energy
-2.93
Log(D) at pH=7.4
1.73
Log(P)
2.87
Log S
-4.86
Log(Vapor Pressure)
-9.55
Melting Point
195.85
pKa Acid
7.18
pKa Basic
1.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9822
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.9502
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9099
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8975
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8959
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8775
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8730
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8710
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8669
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8649
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8629
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8544
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8513
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8422
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8323
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8227
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8221
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8114
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8014
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7993
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7924
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7924
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7836
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7833
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7827
Histidinol dehydrogenase Q8G2R2 HISX_BRUSU Brucella suis biovar 1 3 0.7810
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7800
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 4 0.7794
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7755
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7753
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7744
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7728
Aklavinone 12-hydroxylase RdmE Q54530 DNRF_STREF Streptomyces purpurascens 4 0.7715
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7715
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7676
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7669
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7627
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7618
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.7609
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7553
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7536
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7503
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7486
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.7466
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7460
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 4 0.7454
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7446
Genome polyprotein O93077 O93077_9HEPC Hepacivirus hominis 3 0.7425
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7425
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7396
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7376
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7376
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7372
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7343
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7336
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7335
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7304
Glucose-1-phosphate thymidylyltransferase 1 P37744 RMLA1_ECOLI Escherichia coli 5 0.7302
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7289
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7284
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7250
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7245
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7240
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7206
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7200
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7187
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7178
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7176
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7174
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7164
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7157
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7139
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7136
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7129
Sepiapterin reductase P35270 SPRE_HUMAN Homo sapiens 3 0.7127
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7117
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7111
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7089
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7087
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7067
Petrobactin biosynthesis protein AsbB Q81RQ8 Q81RQ8_BACAN Bacillus anthracis 3 0.7055
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7043
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7038
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7023
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7017
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7011
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7011

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