7-prenyl-indolyl-3-carbaldehyde - Compound Card

7-prenyl-indolyl-3-carbaldehyde

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7-prenyl-indolyl-3-carbaldehyde

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi
  • Class: Indole
    • Subclass: Prenylated Indole
Canonical Smiles O=Cc1c[nH]c2c1cccc2CC=C(C)C
InChI InChI=1S/C14H15NO/c1-10(2)6-7-11-4-3-5-13-12(9-16)8-15-14(11)13/h3-6,8-9,15H,7H2,1-2H3
InChIKey CPXMULPJCYIMIK-UHFFFAOYSA-N
Formula C14H15NO
HBA 1
HBD 1
MW 213.28
Rotatable Bonds 3
TPSA 32.86
LogP 3.49
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 213.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Aspergillus terreus Trichocomaceae Fungi 33178

Showing of synonyms

  • Shaaban M, El-Metwally M.M, et al. (2018). Terretonin M: A new meroterpenoid from the thermophilic Aspergillus terreus TM8 and revision of the absolute configuration of penisimplicins. Nat Prod Res,2018,32(20),2437-2446. [View] [PubMed]
Pubchem: 10965859

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 213.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.52
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
-2.55

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
16.14
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.69
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.04
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.27
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
3.4
Rat (Acute)
1.91
Rat (Chronic Oral)
2.0
Fathead Minnow
4.28
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
338.58
Hydration Free Energy
-9.31
Log(D) at pH=7.4
3.01
Log(P)
3.97
Log S
-4.36
Log(Vapor Pressure)
-6.06
Melting Point
113.95
pKa Acid
10.34
pKa Basic
5.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9439
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9101
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9026
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8945
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8925
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8665
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8626
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8461
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8280
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8238
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8197
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.8183
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8110
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8029
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7988
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7954
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7925
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7923
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7909
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7850
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7825
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7785
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7712
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7701
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7696
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7678
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7669
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7665
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7661
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7656
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7625
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7615
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7583
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7546
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7528
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7524
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7510
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7509
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7497
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7492
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7488
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7488
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7483
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7477
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7475
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7467
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7446
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7439
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7434
Purine phosphoribosyltransferase (GpT-1) Q97W95 Q97W95_SACS2 Saccharolobus solfataricus 3 0.7420
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7401
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7401
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7400
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7387
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7371
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7364
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7364
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7348
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7348
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7344
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7338
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7334
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7329
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7326
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7325
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7323
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7320
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7315
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7314
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7313
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7313
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7309
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7301
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7300
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7291
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7283
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7281
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7277
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7276
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7276
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 2 0.7274
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7272
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7269
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7264
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7256
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7251
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7245
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7238
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7232
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7215
Adenine DNA glycosylase P83847 MUTY_GEOSE Geobacillus stearothermophilus 3 0.7207
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7207
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7204
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7204
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7204
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7194
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7189
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7185
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7182
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7180
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7179
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 2 0.7177
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7171
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7159
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7143
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7143
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7137
Purine nucleoside phosphorylase P50389 PNPH_SACS2 Saccharolobus solfataricus 3 0.7136
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7135
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7116
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7116
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7114
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7098
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7091
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7089
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7088
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7086
5'-methylthioadenosine nucleosidase / s-adenosylhomocysteine nucleosidase Q8YBL1 Q8YBL1_BRUME Brucella melitensis biotype 1 3 0.7084
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7078
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7072
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7069
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7067
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7065
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7063
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7055
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7052
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7049
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7049
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7047
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7046
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7040
Alpha/beta hydrolase fold A5VAT9 A5VAT9_SPHWW Sphingomonas wittichii 2 0.7029
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7024
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7016
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7015
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7010
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7007

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