Janetinine - Compound Card

Janetinine

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Janetinine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles OCc1c2CCN[C@@H](c2cc2c1[nH]c1c2cccc1)C
InChI InChI=1S/C17H18N2O/c1-10-13-8-14-12-4-2-3-5-16(12)19-17(14)15(9-20)11(13)6-7-18-10/h2-5,8,10,18-20H,6-7,9H2,1H3/t10-/m1/s1
InChIKey QEYDVFBZKMXTAR-SNVBAGLBSA-N
Formula C17H18N2O
HBA 2
HBD 3
MW 266.34
Rotatable Bonds 1
TPSA 48.05
LogP 3.02
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 266.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pleiocarpa pycnantha Apocynaceae Plantae 1220085

Showing of synonyms

  • Ndongo JT, Mbing JN, et al. (2018). Carbazole-, aspidofractinine-, and aspidocarpamine-type alkaloids from Pleiocarpa pycnantha.. Journal of natural products,2018, 81(5), 1193-1202. [View] [PubMed]
Pubchem: 145949329

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1c23)[nH]c2cc4c(c3)CNCC4

Level: 0

Mol. Weight: 266.34 g/mol

Cancer cell growth inhibitory

Absorption

Caco-2 (logPapp)
-5.31
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.02
Plasma Protein Binding
51.05
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
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.88
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.22
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.45
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.57
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
0.93
Rat (Acute)
2.18
Rat (Chronic Oral)
2.41
Fathead Minnow
4.23
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
416.17
Hydration Free Energy
-11.8
Log(D) at pH=7.4
2.58
Log(P)
2.18
Log S
-3.89
Log(Vapor Pressure)
-8.86
Melting Point
205.28
pKa Acid
13.66
pKa Basic
8.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9376
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9357
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.9108
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8995
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8769
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8740
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8734
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8722
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8656
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8587
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8562
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8553
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.8463
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8459
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8450
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8449
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8428
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.8380
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8365
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.8347
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8340
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8339
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8332
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8278
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 3 0.8211
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8118
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8108
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8090
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.8075
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8070
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.8026
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8024
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8014
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7999
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.7938
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7903
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7891
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7876
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7858
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7825
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7786
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7751
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7746
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 4 0.7678
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7664
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7660
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7654
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7622
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7618
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7589
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7552
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7549
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7531
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7523
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7522
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7521
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7495
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7469
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7461
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7453
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7448
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7446
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.7433
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7431
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7427
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7425
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7420
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7419
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7413
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7409
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7405
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7403
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7387
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7382
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7381
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 3 0.7377
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 3 0.7376
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7374
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7318
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7310
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7306
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7291
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7290
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7280
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7278
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7253
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7248
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7247
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7246
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7228
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7216
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7211
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7209
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7207
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7206
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 3 0.7201
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7190
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7188
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7165
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7162
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7147
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7144
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7116
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7112
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7108
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7107
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7103
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7089
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7089
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7083
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7080
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7065
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7058
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7055
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7050
Tyrosine-protein kinase ITK/TSK Q08881 ITK_HUMAN Homo sapiens 3 0.7046
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7040
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7030
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7029
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7028
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7022
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7018
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7014
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7010
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7008

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