8-hydroxy-10-methoxy-3-(4hydroxy-3,5-dimethoxyphenyl-2-(hydroxymethyl)-2,3-dihydro-[1,4]dioxino[2,3-c]xanthen-7-one - Compound Card

8-hydroxy-10-methoxy-3-(4hydroxy-3,5-dimethoxyphenyl-2-(hydroxymethyl)-2,3-dihydro-[1,4]dioxino[2,3-c]xanthen-7-one

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8-hydroxy-10-methoxy-3-(4hydroxy-3,5-dimethoxyphenyl-2-(hydroxymethyl)-2,3-dihydro-[1,4]dioxino[2,3-c]xanthen-7-one

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Xanthone
    • Subclass: Xanthonolignoid
Canonical Smiles OC[C@@H]1Oc2c(O[C@H]1c1cc(OC)c(c(c1)OC)O)ccc1c2oc2cc(O)cc(c2c1=O)OC
InChI InChI=1S/C25H22O10/c1-30-15-8-12(27)9-16-20(15)21(28)13-4-5-14-25(24(13)34-16)35-19(10-26)23(33-14)11-6-17(31-2)22(29)18(7-11)32-3/h4-9,19,23,26-27,29H,10H2,1-3H3/t19-,23-/m0/s1
InChIKey YABDPAOZOGBFDS-CVDCTZTESA-N
Formula C25H22O10
HBA 10
HBD 3
MW 482.44
Rotatable Bonds 5
TPSA 137.05
LogP 3.26
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 482.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum roeperianum Hypericaceae Plantae —

Showing of synonyms

  • Damen F, Demgne OMF, et al. (2021). A new polyketide from the bark of Hypericum roeperianum Schimp. (Hypericaceae).. Natural product research,2021, 35(14), 2381-2387. [View] [PubMed]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 482.44 g/mol

Structure

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

Level: 0

Mol. Weight: 482.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 482.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.3
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.480
Plasma Protein Binding
68.51
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
8.220
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.560
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.950
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.300
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
-504.360
Rat (Acute)
2.180
Rat (Chronic Oral)
2.970
Fathead Minnow
6.340
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
568.250
Hydration Free Energy
-3.080
Log(D) at pH=7.4
2.150
Log(P)
2.33
Log S
-6.2
Log(Vapor Pressure)
-9.83
Melting Point
232.58
pKa Acid
7.12
pKa Basic
2.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9480
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9456
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9280
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9272
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9224
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9032
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8970
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8925
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8803
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8801
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8681
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8637
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8630
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8609
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8468
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8431
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8405
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8391
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8361
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8351
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8311
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8274
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8269
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8224
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.8004
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7970
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7962
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.7946
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7933
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7899
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7839
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7821
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7789
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7787
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7778
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7740
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7723
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7693
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7692
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7676
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7648
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7623
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7610
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7602
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7593
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7576
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7570
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7555
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7554
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7513
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7512
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7480
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.7464
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7463
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7441
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7434
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7422
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7421
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7404
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7403
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7390
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7388
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7379
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 4 0.7334
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7287
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7287
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7270
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7250
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7248
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7240
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7238
Tubulin--tyrosine ligase F6Z895 A9ULH4_XENTR Xenopus tropicalis 4 0.7230
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7221
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7212
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7198
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.7188
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7159
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7153
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7153
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7124
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7117
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7105
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7100
Glucose-1-phosphate thymidylyltransferase 1 P37744 RMLA1_ECOLI Escherichia coli 5 0.7095
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 3 0.7064
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7064
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7058
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7047
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7040
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7033
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7018
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7005

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