(E)-4-(1H-indol-5-yl)-but-3-en-2-one - Compound Card

(E)-4-(1H-indol-5-yl)-but-3-en-2-one

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(E)-4-(1H-indol-5-yl)-but-3-en-2-one

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CC(=O)/C=C/c1ccc2c(c1)cc[nH]2
InChI InChI=1S/C12H11NO/c1-9(14)2-3-10-4-5-12-11(8-10)6-7-13-12/h2-8,13H,1H3/b3-2+
InChIKey GZFUNESZCZCIFV-NSCUHMNNSA-N
Formula C12H11NO
HBA 1
HBD 1
MW 185.23
Rotatable Bonds 2
TPSA 32.86
LogP 2.77
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.08
Exact Mass 185.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Monodora minor Annonaceae Plantae 493336

Showing of synonyms

  • Christopher R, Mgani QA, et al. (2021). A new indole alkaloid and other constituents from Monodora minor and Uvaria tanzaniae: their antitrypanosomal and antiplasmodial evaluation. Natural product research,2021, 35(20), 3470-3477. [View] [PubMed]
Pubchem: 69105643
Nmrshiftdb2: 70105752

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 185.23 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.18
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.63
Plasma Protein Binding
57.23
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
8.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.14
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.97
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
3.8
Rat (Acute)
1.78
Rat (Chronic Oral)
2.3
Fathead Minnow
4.25
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
352.13
Hydration Free Energy
-10.65
Log(D) at pH=7.4
2.37
Log(P)
2.12
Log S
-3.74
Log(Vapor Pressure)
-5.73
Melting Point
156.16
pKa Acid
12.56
pKa Basic
6.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9345
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9236
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9194
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9053
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8984
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8965
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8885
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8775
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8256
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8079
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7996
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7951
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7743
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 2 0.7695
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7693
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7692
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7689
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7668
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7644
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7642
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7625
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7599
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7582
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7578
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7578
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7560
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7559
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7551
cAMP-activated global transcriptional regulator Vfr P55222 VFR_PSEAE Pseudomonas aeruginosa 3 0.7538
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7537
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7534
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7526
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7506
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7505
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7500
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7497
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7495
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7483
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7480
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7479
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7479
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7477
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7474
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7467
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7466
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7439
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7427
Envelope glycoprotein gp160 C6G099 C6G099_9HIV1 Human immunodeficiency virus 1 2 0.7415
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7412
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7403
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7393
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7391
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7370
Argininosuccinate synthase P59846 ASSY_THET8 Thermus thermophilus 3 0.7369
Cyclic nucleotide-binding domain-containing protein E0RR11 E0RR11_SPITD Spirochaeta thermophila 2 0.7369
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7366
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7364
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7362
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7357
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7329
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 2 0.7323
Argininosuccinate synthase P59846 ASSY_THET8 Thermus thermophilus 3 0.7313
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7307
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7292
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 2 0.7287
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7286
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7285
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7284
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7278
Metallophosphoesterase A3DJ38 A3DJ38_HUNT2 Clostridium thermocellum 2 0.7277
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7269
D-alanine--D-alanine ligase Q5HEB7 DDL_STAAC Staphylococcus aureus 2 0.7264
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7262
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7258
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7257
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.7254
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7254
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7253
Protein UshA P07024 USHA_ECOLI Escherichia coli 2 0.7252
Albumin P14639 ALBU_SHEEP Ovis aries 2 0.7250
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7249
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 2 0.7247
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7243
Cobalamin synthesis related protein Q6NIF5 Q6NIF5_CORDI Corynebacterium diphtheriae 3 0.7223
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7217
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7216
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7213
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 2 0.7211
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7210
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7209
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7204
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7202
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7199
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7195
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 2 0.7186
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7178
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7176
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7174
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7159
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7141
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7141
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7134
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7129
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7122
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7113
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7111
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7104
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7100
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7095
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7095
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7086
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7083
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7082
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7076
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7069
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7068
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7065
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7058
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7050
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7046
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 2 0.7045
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7032
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7028
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 2 0.7026
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 2 0.7023
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7018
histidine kinase Q9WZV7 Q9WZV7_THEMA Thermotoga maritima 3 0.7007
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 2 0.7002
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7002

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