Bruceolline D - Compound Card

Bruceolline D

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Bruceolline D

Structure
Zoomed Structure
  • Family: Simaroubaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles O=C1Cc2c(C1(C)C)[nH]c1c2cccc1
InChI InChI=1S/C13H13NO/c1-13(2)11(15)7-9-8-5-3-4-6-10(8)14-12(9)13/h3-6,14H,7H2,1-2H3
InChIKey TVRRJWCBPHZRIR-UHFFFAOYSA-N
Formula C13H13NO
HBA 1
HBD 1
MW 199.25
Rotatable Bonds 0
TPSA 32.86
LogP 2.57
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.31
Exact Mass 199.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brucea antidysenterica Simaroubaceae Plantae 459111

Showing of synonyms

  • Makong YS, Fotso GW, et al. (2021). Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from brucea antidysenterica J. F. Mill. (simaroubaceae).. Natural product research,2021, 35(12), 2037-2043. [View] [PubMed]
Pubchem: 12387437
Nmrshiftdb2: 70090659

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)[nH]c2CC(=O)C3

Level: 0

Mol. Weight: 171.2 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.390
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)
0.730
Plasma Protein Binding
16.9
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.430
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.430
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.320
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.390
Micronucleos
Toxic
NR-AhR
Toxic
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
2.880
Rat (Acute)
2.500
Rat (Chronic Oral)
2.140
Fathead Minnow
4.000
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
327.530
Hydration Free Energy
-9.850
Log(D) at pH=7.4
1.920
Log(P)
2.28
Log S
-3.32
Log(Vapor Pressure)
-5.87
Melting Point
186.72
pKa Acid
10.71
pKa Basic
6.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9810
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9791
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9737
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9706
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8764
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8689
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.8615
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8213
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8040
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7991
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7864
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7817
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7783
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7781
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7760
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7756
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 2 0.7737
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7682
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7680
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7670
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7670
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7666
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7653
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7648
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7623
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7619
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7602
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7594
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 2 0.7562
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7539
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7537
Catabolite activator protein C3SQJ7 C3SQJ7_ECOLX Escherichia coli 3 0.7510
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7507
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7497
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7488
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7485
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7482
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7471
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7467
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7454
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7452
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7445
Adenylate cyclase 2 A0A2U2H3Y1 A0A384LKY8_YERPE Yersinia pestis 2 0.7415
D-alanine--D-alanine ligase Q5HEB7 DDL_STAAC Staphylococcus aureus 2 0.7405
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7403
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7376
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7366
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7360
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7360
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7360
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7359
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7348
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7322
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7313
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7303
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7298
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7297
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7291
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 2 0.7288
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7286
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7280
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 2 0.7273
D(3) dopamine receptor P35462 DRD3_HUMAN Homo sapiens 2 0.7266
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7239
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7238
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7231
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7212
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7208
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7205
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7203
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7202
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7188
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7186
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7185
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7182
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7176
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 2 0.7164
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7157
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7151
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7151
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7150
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7150
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7149
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7142
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7136
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7118
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 2 0.7117
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7108
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7105
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 2 0.7105
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 3 0.7102
Thiazole tautomerase P25053 TENI_BACSU Bacillus subtilis 2 0.7100
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 2 0.7093
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 2 0.7088
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7085
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7078
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7078
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7075
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7074
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 2 0.7069
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7067
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7065
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7062
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 2 0.7060
Envelope glycoprotein gp160 Q0ED31 Q0ED31_9HIV1 Human immunodeficiency virus 1 2 0.7059
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7054
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 2 0.7054
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7048
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7040
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7034
Purine nucleoside phosphorylase DeoD-type 1 Q9KPM0 DEOD1_VIBCH Vibrio cholerae serotype O1 3 0.7034
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7024
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7022
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7016
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7015
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7007
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7003

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