8,8-bis-(dihydroconiferyl) diferulate - Compound Card

8,8-bis-(dihydroconiferyl) diferulate

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8,8-bis-(dihydroconiferyl) diferulate

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Methoxyphenol
Canonical Smiles C(=O)(/C=C/c1cc(OC)c(O)cc1)OCC(Cc1ccc(c(c1)OC)O)C(COC(=O)/C=C/c1cc(OC)c(O)cc1)Cc1cc(c(cc1)O)OC
InChI InChI=1S/C40H42O12/c1-47-35-19-25(5-11-31(35)41)9-15-39(45)51-23-29(17-27-7-13-33(43)37(21-27)49-3)30(18-28-8-14-34(44)38(22-28)50-4)24-52-40(46)16-10-26-6-12-32(42)36(20-26)48-2/h5-16,19-22,29-30,41-44H,17-18,23-24H2,1-4H3/b15-9+,16-10+
InChIKey MOFDLYLEJWQRHD-KAVGSWPWSA-N
Formula C40H42O12
HBA 12
HBD 4
MW 714.76
Rotatable Bonds 17
TPSA 170.44
LogP 6.07
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 52
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 714.27
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum roeperianum Hypericaceae Plantae —
2 Hypericum roeperianum Hypericaceae Plantae —

Showing of synonyms

  • Demgne OMF, Damen F, et al. (2021). Botanicals and phytochemicals from the bark of Hypericum roeperianum (Hypericaceae) had strong antibacterial activity and showed synergistic effects with antibiotics against multidrug-resistant bacteria expressing active efflux pumps.. Journal of ethnopharmacology,2021, 277, 114257. [View] [PubMed]
  • Damen F, Simo Mpetga JD, et al. (2022). Roeperone A, a new tetraoxygenated xanthone and other compounds from the leaves of Hypericum roeperianum Schimp. (Hypericaceae).. Natural product research,2022, 36(8), 2071-2077. [View] [PubMed]
Pubchem: 14189379
Nmrshiftdb2: 60070232

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OCC(Cc2ccccc2)C(Cc3ccccc3)COC(=O)C=Cc4ccccc4

Level: 3

Mol. Weight: 714.76 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCC(Cc2ccccc2)CCOC(=O)C=Cc3ccccc3

Level: 3

Mol. Weight: 714.76 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCC(Cc2ccccc2)CCc3ccccc3

Level: 2

Mol. Weight: 714.76 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCCCCOC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 714.76 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCCCCc2ccccc2

Level: 1

Mol. Weight: 714.76 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)OCCCc2ccccc2

Level: 1

Mol. Weight: 714.76 g/mol

Structure

SMILES: c1ccccc1CCCCc2ccccc2

Level: 1

Mol. Weight: 714.76 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 714.76 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-0.290
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
627.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.350
Plasma Protein Binding
51.6
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
10.620
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-12.050
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.040
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.460
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-1142804.590
Rat (Acute)
2.070
Rat (Chronic Oral)
3.460
Fathead Minnow
1453.690
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
122486.420
Hydration Free Energy
-2.920
Log(D) at pH=7.4
5.880
Log(P)
5.09
Log S
-7.65
Log(Vapor Pressure)
-4060.6
Melting Point
181.51
pKa Acid
-1.38
pKa Basic
4.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9527
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9341
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9264
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8986
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8965
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8915
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8898
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8811
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8808
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8734
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8692
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8533
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8491
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8488
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8429
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8393
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8364
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8341
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8324
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8247
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8237
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8236
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8165
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8158
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8149
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8145
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8119
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8111
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8107
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8080
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8053
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8025
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8013
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7996
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7977
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7968
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7940
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7938
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7913
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7801
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7720
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7709
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7697
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7692
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7672
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7658
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7657
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7652
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7636
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7621
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7566
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7542
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7496
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7478
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7478
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7457
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7446
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7445
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7433
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7428
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7425
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7416
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7415
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7412
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7409
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7397
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7374
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7367
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7366
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7362
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7354
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7343
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7340
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7339
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7338
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7313
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.7306
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7303
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7295
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7291
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7285
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7269
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7266
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7264
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7256
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7253
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7238
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7237
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7235
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7227
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7226
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7226
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7224
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7223
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7217
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7213
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7203
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7201
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7179
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7175
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7138
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7136
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7134
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7129
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7109
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7105
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7101
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7100
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7095
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7089
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7088
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7086
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 4 0.7084
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7084
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7078
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7075
Formate--tetrahydrofolate ligase Q2RM91 FTHS_MOOTA Moorella thermoacetica 2 0.7067
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7058
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7053
tRNA(Met) cytidine acetyltransferase TmcA P76562 TMCA_ECOLI Escherichia coli 4 0.7052
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7051
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7050
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7039
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7022
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7022
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7017
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7011
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7004
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7003

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