Bleekerine - Compound Card

Bleekerine

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Bleekerine

Structure
Zoomed Structure
  • Family: Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles COC(=O)C1=CO[C@H]([C@H]2[C@@H]1Cc1n(C2)ccc2c1nc1c2cc(c(c1)OC)OC)C
InChI InChI=1S/C23H24N2O5/c1-12-16-10-25-6-5-13-15-8-20(27-2)21(28-3)9-18(15)24-22(13)19(25)7-14(16)17(11-30-12)23(26)29-4/h5-6,8-9,11-12,14,16H,7,10H2,1-4H3/t12-,14-,16-/m0/s1
InChIKey TWZUULCDVYYPNU-NOLJZWGESA-N
Formula C23H24N2O5
HBA 7
HBD 0
MW 408.45
Rotatable Bonds 3
TPSA 71.81
LogP 3.42
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.39
Exact Mass 408.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pachypodium lamerei Apocynaceae Plantae 69385

Showing of synonyms

  • Mina S.A, Mohamed S.A, et al. (2020). LC-ESI-MS/MS profiling of alkaloids and antiproliferative activity of Pachypoduim lamerei drake leaves. Natural product research, 2020, 34(9), 1292-1296. [View] [PubMed]
Pubchem: 441992
Kegg Ligand: C09046
Chebi: 3138
Nmrshiftdb2: 60070537

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)nc2c4n(cc3)CC5C(C4)C=COC5

Level: 0

Mol. Weight: 276.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.850
Plasma Protein Binding
61.51
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.390
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.950
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.050
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.350
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-60.480
Rat (Acute)
2.540
Rat (Chronic Oral)
1.540
Fathead Minnow
4.620
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
516.760
Hydration Free Energy
-3.520
Log(D) at pH=7.4
3.240
Log(P)
2.87
Log S
-4.66
Log(Vapor Pressure)
-8.44
Melting Point
211.54
pKa Acid
9.7
pKa Basic
6.84
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 0.9643
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9474
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9430
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9370
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9309
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.9170
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9162
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9134
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9107
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8929
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8860
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8823
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8729
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8669
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8629
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8611
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.8608
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8586
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8563
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8556
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8503
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8495
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8440
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8431
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 3 0.8421
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8175
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8123
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7929
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7902
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7899
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7835
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7742
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7730
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7718
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7708
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7697
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7691
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7625
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7597
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7595
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7584
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7580
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7524
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7522
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7459
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7416
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7404
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7390
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7390
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7371
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 2 0.7363
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7358
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7341
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7338
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7327
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7323
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7320
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7316
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 2 0.7304
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7296
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7287
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7284
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7272
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7259
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7242
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7239
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7233
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7196
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7185
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7184
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7153
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7153
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7147
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7139
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7137
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7136
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7127
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7079
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7071
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7062
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7055
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7050
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7049
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7047
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7046
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7044
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7037
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7034
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7029
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7023
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7014
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7007
Phosphoenolpyruvate carboxykinase [GTP] P9WIH3 PCKG_MYCTU Mycobacterium tuberculosis 3 0.7007
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7003

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