Edulinine - Compound Card

Edulinine

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Edulinine

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles COc1c(C[C@H](C(O)(C)C)O)c(=O)n(c2c1cccc2)C
InChI InChI=1S/C16H21NO4/c1-16(2,20)13(18)9-11-14(21-4)10-7-5-6-8-12(10)17(3)15(11)19/h5-8,13,18,20H,9H2,1-4H3/t13-/m1/s1
InChIKey NHNXJYYEQLVCAZ-CYBMUJFWSA-N
Formula C16H21NO4
HBA 5
HBD 2
MW 291.35
Rotatable Bonds 4
TPSA 71.69
LogP 1.22
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 291.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Araliopsis soyauxii Rutaceae Plantae 1317904

Showing of synonyms

  • Noulala CGT, Ouete JLN, et al. (2022). Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae). Molecules. 2022, 27(3), 1104. [View] [PubMed]
Pubchem: 161570
Nmrshiftdb2: 60063102

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)[nH]c(=O)cc2

Level: 0

Mol. Weight: 291.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.050
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.680
Plasma Protein Binding
51.26
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.230
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.060
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.800
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.420
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.760
Rat (Acute)
2.990
Rat (Chronic Oral)
2.050
Fathead Minnow
4.240
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
369.500
Hydration Free Energy
-11.950
Log(D) at pH=7.4
1.370
Log(P)
1.25
Log S
-2.26
Log(Vapor Pressure)
-6.62
Melting Point
158.74
pKa Acid
8.84
pKa Basic
6.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9228
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9051
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9004
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8982
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8964
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8931
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8738
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8587
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8543
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8517
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8502
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8462
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.8376
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8373
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8368
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8299
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8271
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8238
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 4 0.8183
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.8116
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8092
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8027
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8018
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7989
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7975
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7935
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7930
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7890
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7880
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7862
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7856
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7837
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7824
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7806
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7799
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7785
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7747
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7729
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7728
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7675
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7672
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7671
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7665
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7664
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7627
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7622
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7618
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7585
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7582
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7561
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7560
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7540
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7535
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7484
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7478
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7441
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7426
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7415
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7411
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7407
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7399
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7379
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7377
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7365
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7364
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7359
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7287
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7286
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 4 0.7265
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7256
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7255
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7252
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7251
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7250
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7237
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7228
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7220
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7211
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7194
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7189
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7183
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7181
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7175
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7174
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7170
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7156
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7153
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7101
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7091
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7072
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7059
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7054
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7051
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7047
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7038
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7029
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7026
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7020
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7018
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7008

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