3-(1,1-dimethyl-but-2-enyl)-5-(3-methyl-but-2-enyl)-1H-indole - Compound Card

3-(1,1-dimethyl-but-2-enyl)-5-(3-methyl-but-2-enyl)-1H-indole

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3-(1,1-dimethyl-but-2-enyl)-5-(3-methyl-but-2-enyl)-1H-indole

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles C/C=C/C(c1c[nH]c2c1cc(CC=C(C)C)cc2)(C)C
InChI InChI=1S/C19H25N/c1-6-11-19(4,5)17-13-20-18-10-9-15(12-16(17)18)8-7-14(2)3/h6-7,9-13,20H,8H2,1-5H3/b11-6+
InChIKey LGOMEUQGXOHWGQ-IZZDOVSWSA-N
Formula C19H25N
HBA 0
HBD 1
MW 267.42
Rotatable Bonds 4
TPSA 15.79
LogP 5.53
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.37
Exact Mass 267.2
Number of Lipinski Rule Violations 1
# 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: 91263316

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 267.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.27
Plasma Protein Binding
45.73
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
8.5
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
3.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.57
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.2
Micronucleos
Safe
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
3.84
Rat (Acute)
1.92
Rat (Chronic Oral)
2.07
Fathead Minnow
5.06
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Toxic
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
350.53
Hydration Free Energy
-7.49
Log(D) at pH=7.4
4.49
Log(P)
6.46
Log S
-5.62
Log(Vapor Pressure)
-5.22
Melting Point
102.11
pKa Acid
12.64
pKa Basic
7.49
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 0.8437
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8437
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8416
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8416
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8365
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8365
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8262
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8262
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7971
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7971
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7923
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7923
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7910
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7910
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7889
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7889
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7882
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 4 0.7882
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7828
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7828
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7750
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7750
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7747
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7747
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7678
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7678
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7677
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7677
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7663
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7663
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7602
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7602
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7585
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7585
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7569
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7569
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7537
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7537
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7512
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7512
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7401
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7401
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7382
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7382
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7356
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7356
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7344
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7344
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7310
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7310
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7294
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7294
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7288
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7288
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7265
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7265
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7264
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7264
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7228
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7228
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7216
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7216
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7127
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7127
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7114
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7114
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7112
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7112
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7097
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7097
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7049
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7049
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7049
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7049
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7032
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7032
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7025
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7025
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7009
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7009
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7006
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7006

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