4-[3-(1,1-dimethyl-but-2-enyl)-1H-indol-5-yl]-but-3-en-2-one - Compound Card

4-[3-(1,1-dimethyl-but-2-enyl)-1H-indol-5-yl]-but-3-en-2-one

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4-[3-(1,1-dimethyl-but-2-enyl)-1H-indol-5-yl]-but-3-en-2-one

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles C/C=C/C(c1c[nH]c2c1cc(/C=C/C(=O)C)cc2)(C)C
InChI InChI=1S/C18H21NO/c1-5-10-18(3,4)16-12-19-17-9-8-14(11-15(16)17)7-6-13(2)20/h5-12,19H,1-4H3/b7-6+,10-5+
InChIKey CDFJJMVRTWWKOT-XYLIHAQWSA-N
Formula C18H21NO
HBA 1
HBD 1
MW 267.37
Rotatable Bonds 4
TPSA 32.86
LogP 4.62
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.28
Exact Mass 267.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Isolona cauliflora Annonaceae Plantae 489332

Showing of synonyms

  • Nkunya MH, Makangara JJ, et al. (2004). Prenylindoles from Tanzanian Monodora and Isolona species. Natural Product Research,2004,18(3),253-258. [View] [PubMed]
Pubchem: 91583443

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 267.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.31

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.07
Plasma Protein Binding
54.74
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
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.83
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.55
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
4.19
Rat (Acute)
2.05
Rat (Chronic Oral)
2.19
Fathead Minnow
4.93
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
372.74
Hydration Free Energy
-9.5
Log(D) at pH=7.4
3.86
Log(P)
4.38
Log S
-5.57
Log(Vapor Pressure)
-6.36
Melting Point
146.72
pKa Acid
11.52
pKa Basic
6.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8877
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8877
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8728
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8728
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8715
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8715
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8636
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8636
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8520
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8520
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8332
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8332
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8197
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8197
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8076
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8076
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8024
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8024
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8013
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8013
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7954
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7954
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7934
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7934
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7923
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7923
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7785
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7785
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7783
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7783
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7752
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7752
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7705
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7705
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7621
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7621
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7600
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7600
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7588
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7588
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7581
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7581
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7571
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7571
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7557
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7557
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7555
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7555
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7531
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7531
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7521
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7521
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7520
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7520
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7510
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7510
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7508
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7508
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7490
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7490
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7486
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7486
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7463
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7463
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7459
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7459
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7433
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7433
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7416
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7416
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7409
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7409
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7408
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7408
cAMP-activated global transcriptional regulator Vfr P55222 VFR_PSEAE Pseudomonas aeruginosa 3 0.7382
cAMP-activated global transcriptional regulator Vfr P55222 VFR_PSEAE Pseudomonas aeruginosa 3 0.7382
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7377
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7377
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7349
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7349
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7337
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7337
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7331
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7331
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7329
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7329
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7327
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7327
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7312
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7312
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7311
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7311
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7272
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7272
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7268
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7268
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7254
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7254
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7236
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7236
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7235
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7235
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7222
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7222
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7220
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7220
L-seryl-tRNA(Sec) kinase Q58933 PSTK_METJA Methanocaldococcus jannaschii 2 0.7218
L-seryl-tRNA(Sec) kinase Q58933 PSTK_METJA Methanocaldococcus jannaschii 2 0.7218
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7209
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7209
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7200
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7200
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7193
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7193
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7188
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7188
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7183
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7183
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7153
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7153
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7148
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7148
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7143
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7143
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7131
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7131
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7126
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7126
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7118
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7118
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7117
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7117
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7116
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7116
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7109
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7109
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7102
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7102
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7096
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7096
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7084
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7084
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7083
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7083
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7078
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7078
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7055
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7055
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7054
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7054
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7049
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7049
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7048
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7048
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7047
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7047
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7030
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7030
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7023
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7023
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7018
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7018
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7018
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7018
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7017
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7017
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7003
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7003

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