Buntamine - Compound Card

Buntamine

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Buntamine

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Acridine Alkaloid
Canonical Smiles COc1c(O)ccc2c1n(C)c1cc(O)c(c(c1c2=O)O)CC=C(C)C
InChI InChI=1S/C20H21NO5/c1-10(2)5-6-11-15(23)9-13-16(18(11)24)19(25)12-7-8-14(22)20(26-4)17(12)21(13)3/h5,7-9,22-24H,6H2,1-4H3
InChIKey XUUGIWDILRFFER-UHFFFAOYSA-N
Formula C20H21NO5
HBA 6
HBD 3
MW 355.39
Rotatable Bonds 3
TPSA 91.92
LogP 3.33
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 355.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus aurantium Rutaceae Plantae 43166

Showing of synonyms

  • Bissim S, Kenmogne S, et al. (2019). Bioactive acridone alkaloids and their derivatives from Citrus aurantium (Rutaceae). Phytochemistry Letters, 2019, 29, 148-153. [View]
Pubchem: 5281838
Kegg Ligand: C10653
Chebi: 3214
Nmrshiftdb2: 60076646

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)[nH]c3c(c2=O)cccc3

Level: 0

Mol. Weight: 355.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.26
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.030
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.130
Plasma Protein Binding
59.27
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.550
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.850
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.380
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.420
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
2.200
Rat (Acute)
2.230
Rat (Chronic Oral)
2.970
Fathead Minnow
4.960
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
475.710
Hydration Free Energy
-9.670
Log(D) at pH=7.4
2.220
Log(P)
4.31
Log S
-4.95
Log(Vapor Pressure)
-7.77
Melting Point
232.0
pKa Acid
8.85
pKa Basic
7.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9307
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 3 0.9183
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8845
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8783
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8712
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8594
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8503
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8481
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8395
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8350
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8309
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8100
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8092
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.8004
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7968
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 4 0.7965
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.7899
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7875
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7822
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7795
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7751
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7725
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7716
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7707
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7688
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7647
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7617
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7577
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7546
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7540
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7487
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7443
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7397
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7389
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7351
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7349
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7312
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7290
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7253
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7252
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7242
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7240
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7239
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7228
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7196
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7180
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7172
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7171
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7168
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7138
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7117
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7116
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7105
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7096
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7086
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7072
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7071
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7065
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7064
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7063
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7063
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7018
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7002

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