Flindersine - Compound Card

Flindersine

Select a section from the left sidebar

Flindersine

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Angular Pyrano-2-Quinolone
Canonical Smiles O=c1[nH]c2ccccc2c2c1C=CC(O2)(C)C
InChI InChI=1S/C14H13NO2/c1-14(2)8-7-10-12(17-14)9-5-3-4-6-11(9)15-13(10)16/h3-8H,1-2H3,(H,15,16)
InChIKey PXNMNABLQWUMCX-UHFFFAOYSA-N
Formula C14H13NO2
HBA 2
HBD 1
MW 227.26
Rotatable Bonds 0
TPSA 42.09
LogP 2.71
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 227.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Haplophyllum tuberculatum Rutaceae Plantae 452784
2 Fagara chalybea and Fagara holtziana Rutaceae Plantae 1237852

Showing of synonyms

  • Khalid SA, Waterman PG (1981). Alkaloid, lignan and flavonoid constituents of Haplophyllum tuberculatum from Sudan. Planta Medica,1981,43(2),148-152. [View] [PubMed]
  • Taniguchi M, Kubo I. (1993). Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.. Journal of Natural Products,1993,56(9),1539-1546. [View] [PubMed]
Pubchem: 68230
Kegg Ligand: C10679
Chebi: 5094
Nmrshiftdb2: 30001542
CPRiL: 275377
Structure

SMILES: O1CC=Cc(c1c23)c(=O)[nH]c2cccc3

Level: 0

Mol. Weight: 227.26 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.6

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.84
Plasma Protein Binding
29.67
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.9
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
3.49
Rat (Acute)
2.52
Rat (Chronic Oral)
2.0
Fathead Minnow
4.28
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
392.21
Hydration Free Energy
-10.74
Log(D) at pH=7.4
2.66
Log(P)
2.72
Log S
-4.19
Log(Vapor Pressure)
-7.0
Melting Point
234.58
pKa Acid
8.7
pKa Basic
8.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8728
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8728
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8669
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8669
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8268
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8268
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8256
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8256
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8209
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8209
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8026
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8026
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7944
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7944
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7938
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7938
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7920
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7920
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7884
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7884
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7802
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7802
Thymidylate synthase P04818 TYSY_HUMAN Homo sapiens 3 0.7745
Thymidylate synthase P04818 TYSY_HUMAN Homo sapiens 3 0.7745
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7627
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7627
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7595
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.7595
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7545
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7545
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7516
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7516
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7424
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7424
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7407
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7407
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7354
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7354
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7319
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7319
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7297
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7297
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7285
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7285
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7275
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7275
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7249
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7249
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7230
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7230
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7212
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7212
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7203
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7203
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7197
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7197
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7177
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7177
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7153
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7153
Deoxynucleoside kinase Q9XZT6 DNK_DROME Drosophila melanogaster 4 0.7139
Deoxynucleoside kinase Q9XZT6 DNK_DROME Drosophila melanogaster 4 0.7139
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7132
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7132
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7098
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7098
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7078
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7078
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7036
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7036
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7010
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7010

Download SDF