5-methoxyseselin - Compound Card

5-methoxyseselin

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5-methoxyseselin

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Pyranocoumarin
Canonical Smiles COc1cc2OC(C)(C)C=Cc2c2c1ccc(=O)o2
InChI InChI=1S/C15H14O4/c1-15(2)7-6-10-12(19-15)8-11(17-3)9-4-5-13(16)18-14(9)10/h4-8H,1-3H3
InChIKey ZNMRQYJUVCXNGK-UHFFFAOYSA-N
Formula C15H14O4
HBA 4
HBD 0
MW 258.27
Rotatable Bonds 1
TPSA 48.67
LogP 2.99
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 258.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus × paradisi Rutaceae Plantae 37656
2 Citrus x paradisi Rutaceae Plantae 37656

Showing of synonyms

  • Essombe Malolo FA, Bellier Tabekoueng G, et al. (2022). Chemical Constituents of the Stem Bark of the Hybrid Plant Citrus × paradisi Macfad. (Rutaceae).. Chemistry & biodiversity,2022, 19(7), e202101033. [View] [PubMed]
  • Noulala CGT, Ouete JLN, et al. (2023). Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant Citrus × paradisi Macfad (Rutaceae). Molecules. 2023, 28(3), 1078. [View] [PubMed]
Pubchem: 290897
Chebi: 174378
Nmrshiftdb2: 20237246
Bindingdb: 50008732

No compound-protein relationship available.

Structure

SMILES: O=c(o1)ccc(c1c23)ccc2OCC=C3

Level: 0

Mol. Weight: 258.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.140
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.060
Plasma Protein Binding
41.07
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
Non-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
5.940
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.460
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.640
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.330
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
3.880
Rat (Acute)
3.310
Rat (Chronic Oral)
1.650
Fathead Minnow
4.500
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
383.040
Hydration Free Energy
-8.250
Log(D) at pH=7.4
2.910
Log(P)
2.83
Log S
-4.19
Log(Vapor Pressure)
-5.7
Melting Point
163.84
pKa Acid
8.0
pKa Basic
5.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8918
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8620
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8531
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8326
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8101
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8078
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7871
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7692
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7691
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7607
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 3 0.7572
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7511
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7503
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7459
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7453
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7449
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7396
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7311
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7273
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7225
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7224
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7213
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7184
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7150
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7141
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7128
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7062
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7017
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7017
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7004

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