Phellopterin - Compound Card

Phellopterin

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Phellopterin

Structure
Zoomed Structure
  • Family: Apiaceae, Rutaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles COc1c2ccoc2c(c2c1ccc(=O)o2)OCC=C(C)C
InChI InChI=1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3
InChIKey BMLZFLQMBMYVHG-UHFFFAOYSA-N
Formula C17H16O5
HBA 5
HBD 0
MW 300.31
Rotatable Bonds 4
TPSA 61.81
LogP 3.89
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 300.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Clausena anisata Rutaceae Plantae 159034
2 Deverra battandieri Apiaceae Plantae 1589787

Showing of synonyms

  • Esseid C, León F, et al. (2021). Coumarins and other constituents from Deverra battandieri. Phytochemistry Letters, 2021, 42, 129-133.. [View]
  • Tatsimo SJN, Tamokou JDD, et al. (2015). LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata. Med Chem Res, 2015, 24, 1468–1479. [View]
Pubchem: 98608
Kegg Ligand: C17047
Chebi: 80887
Nmrshiftdb2: 60022826
Bindingdb: 81058
CPRiL: 173533
Structure

SMILES: c1coc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 186.17 g/mol

Antibacterial
Cancer cell growth inhibitory

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.27
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.16
Plasma Protein Binding
76.36
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.43
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.8
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.3
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.15
Micronucleos
Toxic
NR-AhR
Toxic
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
2.99
Rat (Acute)
2.56
Rat (Chronic Oral)
2.06
Fathead Minnow
5.1
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
421.44
Hydration Free Energy
-9.07
Log(D) at pH=7.4
3.12
Log(P)
3.89
Log S
-5.02
Log(Vapor Pressure)
-6.69
Melting Point
97.62
pKa Acid
7.25
pKa Basic
6.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9488
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9163
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8933
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8916
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8915
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8888
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8832
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8603
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8568
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8537
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8442
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8284
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8272
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8250
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8223
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8163
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8144
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.8125
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.8084
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8029
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7960
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7959
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7942
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7935
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7909
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7885
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7841
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7828
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7820
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7818
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7817
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 2 0.7800
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7781
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7778
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7774
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7769
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7752
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7745
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7737
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7689
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7687
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7681
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7653
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7652
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7603
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7585
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7572
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7572
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7553
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7544
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7520
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7519
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7510
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7493
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7463
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7462
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7438
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7435
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7429
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7424
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7413
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7412
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7410
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 2 0.7406
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7395
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7381
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7366
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7354
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7353
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7353
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7352
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7340
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7339
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7326
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7313
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7311
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7308
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7298
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7296
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7293
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7289
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7277
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7274
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7268
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 2 0.7264
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7231
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7221
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7201
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7200
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7194
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7189
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7178
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7175
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7170
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7167
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7157
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7151
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7145
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7143
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 2 0.7138
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7123
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7118
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7117
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7116
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7113
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7107
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7095
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7083
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7079
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 2 0.7077
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 2 0.7073
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7064
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7047
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7045
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7027
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7025
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7023
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7022
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7015
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7011
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7009
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7001

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