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4-methoxy-3-(2-methylbut-3-en-2-yl)-6-phenyl-2H-pyran-2-one
- Family: Hypericaceae
- Kingdom: Plantae
-
Class: Pyrone Derivative
- Subclass: Polyketide Derivative
| Canonical Smiles | c1(=O)c(c(cc(o1)c1ccccc1)OC)C(C)(C=C)C |
|---|---|
| InChI | InChI=1S/C17H18O3/c1-5-17(2,3)15-14(19-4)11-13(20-16(15)18)12-9-7-6-8-10-12/h5-11H,1H2,2-4H3 |
| InChIKey | JHFVOPRTYLFUOK-UHFFFAOYSA-N |
| Formula | C17H18O3 |
| HBA | 3 |
| HBD | 0 |
| MW | 270.33 |
| Rotatable Bonds | 4 |
| TPSA | 39.44 |
| LogP | 3.78 |
| Number Rings | 2 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.24 |
| Exact Mass | 270.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Hypericum peplidifolium | Hypericaceae | Plantae | 1321341 |
| 2 | Hypericum roeperianum | Hypericaceae | Plantae | — |
| 3 | Hypericum roeperianum | Hypericaceae | Plantae | — |
Showing of synonyms
4-methoxy-3-(2-methylbut-3-en-2-yl)-6-phenyl-2H-pyran-2-one
NSC603829
87315-06-8
DTXSID40326610
NSC-603829
3-(1,1-Dimethyl-2-propenyl)-4-methoxy-6-phenyl- 2H-pyran-2-one from Hypericum mysorense
- 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]
- Fobofou SA, Harmon CR, et al. (2016). Prenylated phenyl polyketides and acylphloroglucinols from Hypericum peplidifolium.. Phytochemistry,2016, 124, 108-113. [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]
No compound-protein relationship available.
SMILES: c1ccccc1-c2cccc(=O)o2
Level: 1
Mol. Weight: 172.18 g/mol
SMILES: O=c1cccco1
Level: 0
Mol. Weight: 96.08 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 78.11 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -4.44
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.05
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.1
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.09
- Plasma Protein Binding
- 60.43
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.99
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 2.01
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.87
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.2
- Micronucleos
- Safe
- 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
- 4.11
- Rat (Acute)
- 1.83
- Rat (Chronic Oral)
- 1.54
- Fathead Minnow
- 4.67
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 355.05
- Hydration Free Energy
- -9.14
- Log(D) at pH=7.4
- 3.67
- Log(P)
- 3.96
- Log S
- -4.85
- Log(Vapor Pressure)
- -4.7
- Melting Point
- 64.2
- pKa Acid
- 8.97
- pKa Basic
- 3.33
| 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 | 0.9548 |
| Cytochrome P450 | S6BVH1 | S6BVH1_RHOER | Rhodococcus erythropolis | 3 | 0.9308 |
| Glycogen phosphorylase, muscle form | P00489 | PYGM_RABIT | Oryctolagus cuniculus | 3 | 0.9237 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9076 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8934 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8792 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.8673 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.8659 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.8573 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.8545 |
| HTH-type transcriptional regulator EthR | P9WMC1 | ETHR_MYCTU | Mycobacterium tuberculosis | 3 | 0.8542 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8532 |
| Prostaglandin G/H synthase 2 | Q05769 | PGH2_MOUSE | Mus musculus | 3 | 0.8507 |
| Protein S100-A4 | P26447 | S10A4_HUMAN | Homo sapiens | 3 | 0.8354 |
| Methionine aminopeptidase 2 | P50579 | MAP2_HUMAN | Homo sapiens | 3 | 0.8312 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8303 |
| Class B acid phosphatase | Q540U1 | APHA_SALTM | Salmonella typhimurium | 2 | 0.8292 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.8286 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 2 | 0.8138 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.8135 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.8044 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.8041 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.8001 |
| Protoporphyrinogen oxidase | P50336 | PPOX_HUMAN | Homo sapiens | 3 | 0.7943 |
| Cell division cycle 7-related protein kinase | O00311 | CDC7_HUMAN | Homo sapiens | 3 | 0.7926 |
| Calmodulin | P62157 | CALM_BOVIN | Bos taurus | 3 | 0.7922 |
| 2-Hydroxyacid oxidase 1 | Q9UJM8 | HAOX1_HUMAN | Homo sapiens | 3 | 0.7906 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7867 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7851 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 3 | 0.7792 |
| Aldo-keto reductase family 1 member B10 | O60218 | AK1BA_HUMAN | Homo sapiens | 3 | 0.7781 |
| Ectonucleotide pyrophosphatase/phosphodiesterase family member 2 | Q9R1E6 | ENPP2_MOUSE | Mus musculus | 3 | 0.7771 |
| Cytochrome P450 2B4 | P00178 | CP2B4_RABIT | Oryctolagus cuniculus | 3 | 0.7760 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7730 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7730 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 2 | 0.7703 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7699 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7688 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.7686 |
| Sulfotransferase 1E1 | P49888 | ST1E1_HUMAN | Homo sapiens | 3 | 0.7652 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7651 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7651 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7640 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7636 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7626 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7622 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.7615 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7602 |
| Troponin C, slow skeletal and cardiac muscles | P63316 | TNNC1_HUMAN | Homo sapiens | 3 | 0.7601 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7600 |
| Cytochrome P450 2B6 | P20813 | CP2B6_HUMAN | Homo sapiens | 3 | 0.7597 |
| 3',5'-cyclic-AMP phosphodiesterase 4A | P27815 | PDE4A_HUMAN | Homo sapiens | 3 | 0.7589 |
| Oxysterols receptor LXR-beta | P55055 | NR1H2_HUMAN | Homo sapiens | 3 | 0.7577 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7557 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7527 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7527 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7489 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7473 |
| Proto-oncogene tyrosine-protein kinase receptor Ret | P07949 | RET_HUMAN | Homo sapiens | 3 | 0.7472 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7447 |
| cGMP-dependent protein kinase, putative | A5K0N4 | A5K0N4_PLAVS | Plasmodium vivax | 3 | 0.7446 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7437 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7424 |
| Protein S100-A13 | Q99584 | S10AD_HUMAN | Homo sapiens | 2 | 0.7420 |
| Angiopoietin-1 receptor | Q02763 | TIE2_HUMAN | Homo sapiens | 3 | 0.7405 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7403 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 2 | 0.7403 |
| Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic | P80030 | FABI_BRANA | Brassica napus | 3 | 0.7399 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7394 |
| Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 2 | 0.7390 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7383 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7369 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7365 |
| Prostaglandin G/H synthase 2 | Q05769 | PGH2_MOUSE | Mus musculus | 3 | 0.7346 |
| Glutamine synthetase | P9WN39 | GLN1B_MYCTU | Mycobacterium tuberculosis | 3 | 0.7338 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7337 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7335 |
| Glucose-1-phosphate thymidylyltransferase | Q9HU22 | Q9HU22_PSEAE | Pseudomonas aeruginosa | 3 | 0.7332 |
| Anthranilate phosphoribosyltransferase | P9WFX5 | TRPD_MYCTU | Mycobacterium tuberculosis | 2 | 0.7331 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7321 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7321 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7321 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7319 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 2 | 0.7312 |
| Enoyl-ACP reductase | Q9BJJ9 | Q9BJJ9_PLAFA | Plasmodium falciparum | 3 | 0.7311 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7286 |
| Acetylcholinesterase | P22303 | ACES_HUMAN | Homo sapiens | 2 | 0.7285 |
| Acyl-coenzyme A synthetase ACSM2A, mitochondrial | Q08AH3 | ACS2A_HUMAN | Homo sapiens | 2 | 0.7278 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7263 |
| Phytohormone-binding protein CSBP | A0A1S3THR8 | PHBP_VIGRR | Vigna radiata var. radiata | 2 | 0.7258 |
| Casein kinase I isoform gamma-3 | Q9Y6M4 | KC1G3_HUMAN | Homo sapiens | 3 | 0.7252 |
| Transthyretin | P02767 | TTHY_RAT | Rattus norvegicus | 2 | 0.7233 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 3 | 0.7229 |
| Ketimine reductase mu-crystallin | O54983 | CRYM_MOUSE | Mus musculus | 2 | 0.7203 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7202 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7198 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7195 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7192 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 2 | 0.7191 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7191 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7174 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7157 |
| Hexokinase-4 | P35557 | HXK4_HUMAN | Homo sapiens | 2 | 0.7147 |
| Enoyl-[acyl-carrier-protein] reductase [NADH] | P9WGR1 | INHA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7137 |
| Enoyl-ACP reductase | Q9BH77 | Q9BH77_PLAFA | Plasmodium falciparum | 3 | 0.7128 |
| Troponin C, slow skeletal and cardiac muscles | P63316 | TNNC1_HUMAN | Homo sapiens | 3 | 0.7114 |
| Riboflavin biosynthesis protein | Q9WZW1 | Q9WZW1_THEMA | Thermotoga maritima | 3 | 0.7107 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 2 | 0.7106 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7104 |
| Glutathione S-transferase P | P09211 | GSTP1_HUMAN | Homo sapiens | 2 | 0.7093 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7075 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7073 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7062 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 2 | 0.7059 |
| Myosin light chain kinase family member 4 | Q86YV6 | MYLK4_HUMAN | Homo sapiens | 3 | 0.7054 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7038 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7037 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7029 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 2 | 0.7029 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7027 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7017 |
| Ephrin type-B receptor 4 | P54760 | EPHB4_HUMAN | Homo sapiens | 3 | 0.7015 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7013 |
| Dihydroorotate dehydrogenase (quinone), mitochondrial | Q08210 | PYRD_PLAF7 | Plasmodium falciparum | 3 | 0.7006 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7003 |