4-methoxy-3-(2-methylbut-3-en-2-yl)-6-phenyl-2H-pyran-2-one - Compound Card

4-methoxy-3-(2-methylbut-3-en-2-yl)-6-phenyl-2H-pyran-2-one

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4-methoxy-3-(2-methylbut-3-en-2-yl)-6-phenyl-2H-pyran-2-one

Structure
Zoomed Structure
  • Family: Plantae - 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

  • 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]
Pubchem: 354007

No compound-protein relationship available.

Structure

SMILES: c1ccccc1-c2cccc(=O)o2

Level: 1

Mol. Weight: 270.33 g/mol

Structure

SMILES: O=c1cccco1

Level: 0

Mol. Weight: 270.33 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 270.33 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

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