Indole-beta-carboxylic acid - Compound Card

Indole-beta-carboxylic acid

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Indole-beta-carboxylic acid

Structure
Zoomed Structure
  • Family: Fungi - Trichocomaceae
  • Kingdom: Fungi, Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles OC(=O)c1c[nH]c2c1cccc2
InChI InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)
InChIKey KMAKOBLIOCQGJP-UHFFFAOYSA-N
Formula C9H7NO2
HBA 1
HBD 2
MW 161.16
Rotatable Bonds 1
TPSA 53.09
LogP 1.87
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 12
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 161.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Diplodia quercivora Botryosphaeriaceae Fungi 1281306
2 Aspergillus terreus Trichocomaceae Fungi 33178
3 Saccocalyx saturejoides Lamiaceae Plantae 751886
4 Solanum nigrum Solanaceae Plantae 4112

Showing of synonyms

  • Kherkhache H, Benabdelaziz I, et al. (2020). A new indole alkaloid, antioxidant and antibacterial activities of crude extracts from Saccocalyx satureioides. Natural product research, 2020, 34(11), 1528-1534. [View] [PubMed]
  • Abdou R, Scherlach K, et al. (2010). Botryorhodines A–D, antifungal and cytotoxic depsidones from Botryosphaeria rhodina, an endophyte of the medicinal plant Bidens pilosa. Phytochemistry,2010,71(1),110-116. [View] [PubMed]
  • El-Hawary S.S, Sayed A.M, et al. (2017). Secondary metabolites from fungal endophytes of Solanum nigrum. Natural product research, 2017, 31(21), 2568-2571. [View] [PubMed]
  • 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: 69867
Chebi: 24809
Nmrshiftdb2: 20050535
Metabolights: MTBLC24809
Pdb Ligand: ICO
Bindingdb: 93015
CPRiL: 72668
Structure

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 161.16 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.2
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.8

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.92
Plasma Protein Binding
29.4
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
7.18
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.0
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.94
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.68
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
1.57
Rat (Acute)
1.87
Rat (Chronic Oral)
3.06
Fathead Minnow
3.81
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
326.82
Hydration Free Energy
-9.91
Log(D) at pH=7.4
-0.88
Log(P)
1.99
Log S
-3.03
Log(Vapor Pressure)
-5.89
Melting Point
228.59
pKa Acid
5.12
pKa Basic
2.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9706
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9706
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9455
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9455
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9410
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9410
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9376
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9376
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9138
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.9138
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 3 0.9010
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 3 0.9010
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.9003
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.9003
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.8945
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.8945
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8494
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8494
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.8341
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.8341
Albumin P14639 ALBU_SHEEP Ovis aries 3 0.8312
Albumin P14639 ALBU_SHEEP Ovis aries 3 0.8312
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8084
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8084
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8039
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8039
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7969
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7969
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7962
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7962
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7910
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7910
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7854
Eugenol synthase 1 Q15GI4 EGS1_OCIBA Ocimum basilicum 3 0.7854
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7757
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7757
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7729
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7729
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 3 0.7686
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 3 0.7686
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7667
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7667
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7660
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7660
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7659
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7659
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7653
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7653
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7579
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7579
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7545
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7545
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7504
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7504
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7496
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.7496
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7492
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7492
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7480
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7480
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7463
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7463
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7462
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7462
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7461
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7461
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7448
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7448
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7438
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7438
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7434
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7434
Cysteine synthase 1 P47998 CYSK1_ARATH Arabidopsis thaliana 3 0.7429
Cysteine synthase 1 P47998 CYSK1_ARATH Arabidopsis thaliana 3 0.7429
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7416
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7416
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 2 0.7414
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 2 0.7414
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7397
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7397
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7387
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7387
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7383
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7383
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7331
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7331
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7321
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7321
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 2 0.7320
L-lactate dehydrogenase Q27743 LDH_PLAFD Plasmodium falciparum 2 0.7320
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7304
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7304
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7302
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7302
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 2 0.7284
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 2 0.7284
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7272
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7272
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7272
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7272
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7263
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7263
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7260
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7260
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7260
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7260
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 2 0.7248
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 2 0.7248
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7246
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7246
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7240
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7240
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7240
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7240
Adenine DNA glycosylase P83847 MUTY_GEOSE Geobacillus stearothermophilus 3 0.7209
Adenine DNA glycosylase P83847 MUTY_GEOSE Geobacillus stearothermophilus 3 0.7209
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7191
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7191
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7189
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7189
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7182
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7182
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7180
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7180
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7172
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7172
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7164
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7164
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7151
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7151
Purine phosphoribosyltransferase (GpT-1) Q97W95 Q97W95_SACS2 Saccharolobus solfataricus 3 0.7124
Purine phosphoribosyltransferase (GpT-1) Q97W95 Q97W95_SACS2 Saccharolobus solfataricus 3 0.7124
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7124
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7124
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7121
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7121
Farnesyl pyrophosphate synthase Q86C09 Q86C09_9TRYP Trypanosoma brucei 2 0.7099
Farnesyl pyrophosphate synthase Q86C09 Q86C09_9TRYP Trypanosoma brucei 2 0.7099
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7095
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7095
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7094
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7094
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 2 0.7075
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 2 0.7075
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7069
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7069
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7065
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7065
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7057
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7057
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7053
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7053
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7052
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7052
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7020
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7020
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7007
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7007
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7007
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7007
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7003
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7003

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