Beta-carboline-1-propionic acid - Compound Card

Beta-carboline-1-propionic acid

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Beta-carboline-1-propionic acid

Structure
Zoomed Structure
  • Family: Plantae - Simaroubaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Beta-Carboline Alkaloid
Canonical Smiles OC(=O)CCc1nccc2c1[nH]c1c2cccc1
InChI InChI=1S/C14H12N2O2/c17-13(18)6-5-12-14-10(7-8-15-12)9-3-1-2-4-11(9)16-14/h1-4,7-8,16H,5-6H2,(H,17,18)
InChIKey CNUHEVWYPKFJHH-UHFFFAOYSA-N
Formula C14H12N2O2
HBA 2
HBD 2
MW 240.26
Rotatable Bonds 3
TPSA 65.98
LogP 2.73
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.14
Exact Mass 240.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brucea antidysenterica Simaroubaceae Plantae 459111

Showing of synonyms

  • Makong YS, Mouthé Happi G, et al. (2019). Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae). Molecules, 2019, 24(23), 4412. [View] [PubMed]
Pubchem: 5375436
Chebi: 190929
Nmrshiftdb2: 20144370

No compound-protein relationship available.

Structure

SMILES: c1cncc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 240.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.22
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.28
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.68
Plasma Protein Binding
50.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
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
2.67
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.19
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.05
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.91
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
2.52
Rat (Acute)
2.23
Rat (Chronic Oral)
1.97
Fathead Minnow
4.1
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
413.04
Hydration Free Energy
-12.29
Log(D) at pH=7.4
-0.48
Log(P)
2.4
Log S
-3.56
Log(Vapor Pressure)
-8.57
Melting Point
236.69
pKa Acid
7.43
pKa Basic
7.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.9628
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.9513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.9461
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 3 0.9155
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.9089
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8993
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8984
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8953
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8947
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8851
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8804
Metallophosphoesterase A3DJ38 A3DJ38_HUNT2 Clostridium thermocellum 3 0.8791
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 3 0.8765
D(3) dopamine receptor P35462 DRD3_HUMAN Homo sapiens 3 0.8743
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8700
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8636
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8603
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8573
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8491
Ribonuclease J Q72JJ7 RNJ_THET2 Thermus thermophilus 3 0.8402
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.8391
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8380
M17 leucyl aminopeptidase Q8IL11 Q8IL11_PLAF7 Plasmodium falciparum 3 0.8367
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8367
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8364
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8324
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8319
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.8290
Anhydro-N-acetylmuramic acid kinase Q9I5Q5 ANMK_PSEAE Pseudomonas aeruginosa 3 0.8279
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8271
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8260
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8203
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8113
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.8108
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8094
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 3 0.8084
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8058
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8055
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8023
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7997
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7967
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7960
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7949
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.7946
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7916
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7845
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7830
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.7793
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7780
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7746
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 3 0.7741
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7720
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 3 0.7669
Gamma-aminobutyric acid type B receptor subunit 1 Q9UBS5 GABR1_HUMAN Homo sapiens 3 0.7629
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7621
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7612
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7566
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7556
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7550
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.7529
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7504
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7501
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7487
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7473
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7444
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7434
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7421
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7411
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 3 0.7388
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7375
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7364
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7358
Catabolite activator protein C3SQJ7 C3SQJ7_ECOLX Escherichia coli 3 0.7352
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7338
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7328
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7312
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7307
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7303
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7302
Cytosol aminopeptidase P00727 AMPL_BOVIN Bos taurus 2 0.7269
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7265
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7263
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7257
Albumin P14639 ALBU_SHEEP Ovis aries 3 0.7256
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 2 0.7256
Aminopeptidase A2V759 A2V759_9BACL Aneurinibacillus sp. AM-1 3 0.7253
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7249
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7243
L-malyl-CoA/beta-methylmalyl-CoA lyase Q3J5L6 MCAL_RHOS4 Cereibacter sphaeroides 3 0.7217
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7215
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.7213
Formylmethanofuran--tetrahydromethanopterin formyltransferase Q49610 FTR_METKA Methanopyrus kandleri 3 0.7212
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7203
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7179
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7174
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 2 0.7166
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7162
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 2 0.7156
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 3 0.7156
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.7155
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 2 0.7154
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 3 0.7153
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7149
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7139
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 3 0.7133
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7122
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7119
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7112
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7111
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7110
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7106
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7100
Ribosome-inactivating protein alpha-trichosanthin P09989 RIPT_TRIKI Trichosanthes kirilowii 3 0.7073
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 2 0.7054
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7043
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7029
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7027
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7023
Isoleucine--tRNA ligase P56690 SYI_THET8 Thermus thermophilus 3 0.7018
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7002

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