(3-(3-methyl-1-oxo-2-butenyl))-1H-indole - Compound Card

(3-(3-methyl-1-oxo-2-butenyl))-1H-indole

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(3-(3-methyl-1-oxo-2-butenyl))-1H-indole

Structure
Zoomed Structure
  • Family: Plantae - Simaroubaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CC(=CC(=O)c1c[nH]c2c1cccc2)C
InChI InChI=1S/C13H13NO/c1-9(2)7-13(15)11-8-14-12-6-4-3-5-10(11)12/h3-8,14H,1-2H3
InChIKey PGSPKBQWDJNJLS-UHFFFAOYSA-N
Formula C13H13NO
HBA 1
HBD 1
MW 199.25
Rotatable Bonds 2
TPSA 32.86
LogP 3.32
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 199.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brucea antidysenterica Simaroubaceae Plantae 459111

Showing of synonyms

  • Makong YS, Fotso GW, et al. (2021). Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from brucea antidysenterica J. F. Mill. (simaroubaceae).. Natural product research,2021, 35(12), 2037-2043. [View] [PubMed]
Pubchem: 11805712
Nmrshiftdb2: 70069269

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 199.25 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.12
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
26.01
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
8.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.97
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.59
Micronucleos
Toxic
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
3.67
Rat (Acute)
2.02
Rat (Chronic Oral)
2.36
Fathead Minnow
4.17
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
330.5
Hydration Free Energy
-9.42
Log(D) at pH=7.4
2.92
Log(P)
3.21
Log S
-4.03
Log(Vapor Pressure)
-5.64
Melting Point
134.6
pKa Acid
10.75
pKa Basic
6.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9327
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.9201
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.9007
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9004
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8963
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8928
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8771
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8691
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8634
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8537
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8502
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8460
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8385
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8345
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8213
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8156
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8050
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7899
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7881
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7852
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.7851
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7836
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7831
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7810
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7803
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7796
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7794
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7752
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7751
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7665
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7633
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7631
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7617
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7608
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7600
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7597
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7595
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7594
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7583
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7574
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7549
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7532
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7525
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7519
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7514
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7511
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7503
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7500
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7498
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7475
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7457
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7451
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7443
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7431
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7423
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7400
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7398
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7388
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7373
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7358
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7353
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7345
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7343
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7335
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7333
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7331
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7329
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7326
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7325
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7323
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7318
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7317
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7296
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7281
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7277
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7256
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7245
Vitamin D3 receptor A Q9PTN2 VDRA_DANRE Danio rerio 3 0.7242
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7242
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7236
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7231
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7227
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7217
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7206
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7190
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7189
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7188
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7184
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7184
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7174
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7166
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7160
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7146
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 2 0.7144
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7144
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7121
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7120
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7115
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7111
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7105
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7093
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7091
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7088
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7087
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7086
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7086
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7084
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7080
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7078
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7070
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7060
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7055
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7054
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7054
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7052
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7048
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7043
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7041
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7035
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7029
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7023
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7020
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7016
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7016
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7014
Purine nucleoside phosphorylase P50389 PNPH_SACS2 Saccharolobus solfataricus 3 0.7013

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