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

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

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

Structure
Zoomed Structure
  • Family: 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)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/t18-,22-/m0/s1
InChIKey ZIXRDOIIRHBBIP-AVRDEDQJSA-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 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]
Pubchem: 162852391
Nmrshiftdb2: 70132053

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
-5.020
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.350
Plasma Protein Binding
70.59
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
8.860
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.260
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.000
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.950
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
-289.590
Rat (Acute)
2.230
Rat (Chronic Oral)
3.170
Fathead Minnow
5.540
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
582.180
Hydration Free Energy
-2.990
Log(D) at pH=7.4
2.340
Log(P)
2.61
Log S
-6.15
Log(Vapor Pressure)
-10.21
Melting Point
244.69
pKa Acid
6.94
pKa Basic
2.25
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9522
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9303
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9281
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9233
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9223
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.9063
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9039
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.9038
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9037
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8845
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8834
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8773
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8692
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8682
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8592
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8467
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8465
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8424
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8419
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8398
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8343
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8288
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8274
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 4 0.8265
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8250
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8195
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8178
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8159
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8120
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8115
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8063
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8023
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 4 0.7996
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.7970
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.7899
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7842
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7800
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7762
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7755
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7707
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7675
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7660
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7646
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7553
Uracil-DNA glycosylase P13051 UNG_HUMAN Homo sapiens 4 0.7549
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7545
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7538
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7506
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7498
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7496
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.7480
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.7443
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7439
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7436
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7327
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 4 0.7325
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 4 0.7309
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7307
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7295
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7284
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7268
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7263
Rho family GTPase C4M4W4 C4M4W4_ENTHI Entamoeba histolytica 4 0.7248
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7233
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7231
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7212
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7193
DNA mismatch repair protein MutS P23909 MUTS_ECOLI Escherichia coli 3 0.7166
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7150
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7150
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7135
Glucose-1-phosphate thymidylyltransferase 1 P37744 RMLA1_ECOLI Escherichia coli 5 0.7130
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7129
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7114
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7110
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7103
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7097
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7066
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7055
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7049
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7046
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7039
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7033
Uracil-DNA glycosylase P9WFQ9 UNG_MYCTU Mycobacterium tuberculosis 4 0.7024

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