Peplidiforone A - Compound Card

Peplidiforone A

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Peplidiforone A

Structure
Zoomed Structure
  • Family: Hypericaceae
  • Kingdom: Plantae
  • Class: Phenyl Polyketide
    • Subclass: Polyketide Derivative
Canonical Smiles c1(ccccc1)c1cc(c(c(=O)o1)C(C=C)(C)C)O
InChI InChI=1S/C16H16O3/c1-4-16(2,3)14-12(17)10-13(19-15(14)18)11-8-6-5-7-9-11/h4-10,17H,1H2,2-3H3
InChIKey XCHJZOGJYTVDCM-UHFFFAOYSA-N
Formula C16H16O3
HBA 3
HBD 1
MW 256.3
Rotatable Bonds 3
TPSA 50.44
LogP 3.48
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 256.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypericum peplidifolium Hypericaceae Plantae 1321341

Showing of synonyms

  • Fobofou SA, Harmon CR, et al. (2016). Prenylated phenyl polyketides and acylphloroglucinols from Hypericum peplidifolium.. Phytochemistry,2016, 124, 108-113. [View] [PubMed]
Pubchem: 86134572
Nmrshiftdb2: 70079520

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c2cccc(=O)o2

Level: 1

Mol. Weight: 172.18 g/mol

Structure

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 96.08 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.1
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.15

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.09
Plasma Protein Binding
65.53
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.62
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
5.86
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
4.17
Rat (Acute)
2.11
Rat (Chronic Oral)
1.71
Fathead Minnow
4.42
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
356.65
Hydration Free Energy
-10.12
Log(D) at pH=7.4
3.28
Log(P)
3.34
Log S
-4.33
Log(Vapor Pressure)
-6.0
Melting Point
87.88
pKa Acid
7.44
pKa Basic
3.94
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9536
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.9236
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8999
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8973
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8778
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 3 0.8742
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8593
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8557
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8556
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8528
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8346
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8331
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.8330
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 3 0.8324
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.8255
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8255
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 4 0.8247
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8200
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8174
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8105
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8078
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8077
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8039
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8037
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7993
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7972
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7936
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7936
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7901
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7882
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7853
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7853
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7835
2-Hydroxyacid oxidase 1 Q9UJM8 HAOX1_HUMAN Homo sapiens 3 0.7821
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7818
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7792
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7787
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 Q9R1E6 ENPP2_MOUSE Mus musculus 3 0.7777
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7775
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7756
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7730
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7706
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7671
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7616
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7616
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.7611
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7610
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7604
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7570
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7565
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7562
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7560
Cytochrome P450 2B6 P20813 CP2B6_HUMAN Homo sapiens 3 0.7554
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7552
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7521
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7493
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7493
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7490
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7484
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7465
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7452
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7449
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7444
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7433
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7432
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7421
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7413
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7411
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7397
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7394
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7393
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7387
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7385
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7379
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7378
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7361
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7351
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7351
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7347
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7343
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7342
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7341
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7332
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7310
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7298
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7294
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7293
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7275
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7264
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7258
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 3 0.7225
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7224
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7214
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7212
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7210
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7210
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7206
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7200
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7193
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7193
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7187
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7184
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7170
Nucleoside diphosphate kinase, cytosolic P22887 NDKC_DICDI Dictyostelium discoideum 3 0.7155
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7152
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7151
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 3 0.7148
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7146
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7142
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7136
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 3 0.7113
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7108
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7102
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7085
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7083
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 3 0.7078
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7070
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7067
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7066
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7063
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7035
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 3 0.7022
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7002

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