Hyperenone E - Compound Card

Hyperenone E

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Hyperenone E

Structure
Zoomed Structure
  • Family: Plantae - Hypericaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles C=CC(c1c(OC)oc(cc1=O)c1ccc(cc1)O)(C)C
InChI InChI=1S/C17H18O4/c1-5-17(2,3)15-13(19)10-14(21-16(15)20-4)11-6-8-12(18)9-7-11/h5-10,18H,1H2,2-4H3
InChIKey RORVUNDSLYSUCB-UHFFFAOYSA-N
Formula C17H18O4
HBA 4
HBD 1
MW 286.33
Rotatable Bonds 4
TPSA 59.67
LogP 3.48
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 286.12
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: c1ccccc1-c2cc(=O)cco2

Level: 1

Mol. Weight: 286.33 g/mol

Structure

SMILES: O=c1ccocc1

Level: 0

Mol. Weight: 286.33 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 286.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.31
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.15
Plasma Protein Binding
60.83
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
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
6.44
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.72
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.15
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.3
Micronucleos
Toxic
NR-AhR
Safe
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
4.04
Rat (Acute)
2.08
Rat (Chronic Oral)
1.73
Fathead Minnow
4.57
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
384.23
Hydration Free Energy
-10.77
Log(D) at pH=7.4
3.49
Log(P)
3.75
Log S
-4.51
Log(Vapor Pressure)
-6.39
Melting Point
127.73
pKa Acid
9.18
pKa Basic
4.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9817
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.9219
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.9058
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9036
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8918
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8907
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8850
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.8830
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8782
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8709
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8686
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8605
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8571
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8567
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8478
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8471
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8436
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8414
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8382
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8373
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8311
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8222
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8108
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8053
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8031
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8031
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8016
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7992
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7936
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7812
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7802
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7798
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 3 0.7773
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7769
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7765
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7733
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7731
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7706
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7688
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7655
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7639
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7632
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7631
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7630
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7625
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7596
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7590
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7579
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7577
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 4 0.7559
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7550
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7547
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7541
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 3 0.7534
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7531
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7515
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7469
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7463
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7461
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7443
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7428
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7428
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7420
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7414
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7397
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7395
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7395
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7380
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7359
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7355
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7354
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7348
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7347
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7325
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 4 0.7311
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7308
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7298
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7296
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7293
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7292
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7290
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7288
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7286
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7273
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7264
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7264
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7257
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7256
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7245
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic P80030 FABI_BRANA Brassica napus 3 0.7232
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7215
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7212
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7210
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7205
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7198
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7195
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7193
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7191
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7185
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7182
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7160
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7158
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7155
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7153
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7151
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7139
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7125
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7123
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7120
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7118
Bifunctional dihydrofolate reductase-thymidylate synthase Q27783 DRTS_TRYBB Trypanosoma brucei brucei 4 0.7115
Enoyl-acyl carrier protein reductase Q6TEI5 Q6TEI5_PLABE Plasmodium berghei 3 0.7114
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7112
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7104
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7095
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7075
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7071
Myosin light chain kinase family member 4 Q86YV6 MYLK4_HUMAN Homo sapiens 3 0.7063
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7058
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 2 0.7054
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7051
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7048
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7045
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7041
Myeloperoxidase P05164 PERM_HUMAN Homo sapiens 4 0.7029
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7016
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7013
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7008
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7005
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7001

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