(E)-5-(3-methylbuta-1,3-dienyl)-1H-indole - Compound Card

(E)-5-(3-methylbuta-1,3-dienyl)-1H-indole

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(E)-5-(3-methylbuta-1,3-dienyl)-1H-indole

Structure
Zoomed Structure
  • Family: Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CC(=C)/C=C/c1ccc2c(c1)cc[nH]2
InChI InChI=1S/C13H13N/c1-10(2)3-4-11-5-6-13-12(9-11)7-8-14-13/h3-9,14H,1H2,2H3/b4-3+
InChIKey JZJBGWYDNDZHIE-ONEGZZNKSA-N
Formula C13H13N
HBA 0
HBD 1
MW 183.25
Rotatable Bonds 2
TPSA 15.79
LogP 3.76
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.08
Exact Mass 183.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Isolona cauliflora Annonaceae Plantae 489332
2 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]
  • Makangara JJ, Henry L, et al. (2004). The caulindoles: dimeric prenylindoles from Isolona cauliflora. Phytochemistry,2004,65(2),227-232. [View] [PubMed]
Pubchem: 91987572

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 117.15 g/mol

Antifungal

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.27
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.01
Plasma Protein Binding
43.34
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
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
8.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
2.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.46
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.38
Micronucleos
Toxic
NR-AhR
Toxic
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
4.49
Rat (Acute)
1.93
Rat (Chronic Oral)
2.5
Fathead Minnow
4.39
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
332.09
Hydration Free Energy
-7.41
Log(D) at pH=7.4
3.4
Log(P)
3.87
Log S
-4.55
Log(Vapor Pressure)
-4.57
Melting Point
116.55
pKa Acid
13.1
pKa Basic
4.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9245
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9245
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9215
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9215
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8867
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8867
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8234
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8234
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8195
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8195
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.8186
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.8186
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8104
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8104
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8090
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8090
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.8021
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.8021
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7963
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7963
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7961
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7961
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7880
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7880
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7864
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7864
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7862
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7862
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7803
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7803
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7798
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7798
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7757
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7757
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7729
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7729
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7729
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7729
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7697
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7697
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7677
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7677
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7636
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7636
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7628
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7628
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7607
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7607
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7605
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7605
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7600
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7600
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7589
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7589
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 2 0.7575
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7575
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 2 0.7575
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7575
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7566
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7566
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7564
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7564
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7551
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7551
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7537
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7537
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7528
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7528
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7502
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7502
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7488
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7488
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7488
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7488
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7483
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7483
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7474
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7474
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7470
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7470
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7470
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7470
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7469
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7469
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7418
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7418
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7410
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7410
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7391
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7391
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7382
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7382
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7379
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7379
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7373
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7373
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7370
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7370
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7354
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7354
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 2 0.7343
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 2 0.7343
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7338
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7338
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7330
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7330
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7327
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7327
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7326
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7326
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7300
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7300
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7292
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7292
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7274
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7274
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7263
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7263
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7261
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7261
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7256
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7256
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7247
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7247
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7231
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7231
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7228
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7228
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7227
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7227
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7213
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7213
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7199
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7199
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7198
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7198
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7187
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7187
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7139
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7139
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7138
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7138
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7132
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7132
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7130
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7130
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 2 0.7126
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 2 0.7126
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7109
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7109
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7083
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7083
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7064
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7064
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 2 0.7063
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 2 0.7063
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7051
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7051
Albumin P14639 ALBU_SHEEP Ovis aries 2 0.7050
Albumin P14639 ALBU_SHEEP Ovis aries 2 0.7050
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7038
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7038
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7038
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7038
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7025
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7025
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7022
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7022
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7014
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7014
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7004
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7004

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