Latifoliaindole B - Compound Card

Latifoliaindole B

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Latifoliaindole B

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Monoterpenoid Indole Alkaloid
Canonical Smiles CC(c1coc2c1cc1c3[nH]c4c(c3CCn1c2=O)cccc4)O
InChI InChI=1S/C19H16N2O3/c1-10(22)14-9-24-18-13(14)8-16-17-12(6-7-21(16)19(18)23)11-4-2-3-5-15(11)20-17/h2-5,8-10,20,22H,6-7H2,1H3
InChIKey ROKKVZCZBYYCSY-UHFFFAOYSA-N
Formula C19H16N2O3
HBA 4
HBD 2
MW 320.35
Rotatable Bonds 1
TPSA 71.16
LogP 3.35
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 320.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Nauclea latifolia Rubiaceae Plantae 43573

Showing of synonyms

  • Kezetas Bankeu JJ, Kenou Kagho DU, et al. (2019). Constituents from Nauclea latifolia with Anti-Haemophilus influenzae Type b Inhibitory Activities.. Journal of natural products,2019, 82(9), 2580-2585. [View] [PubMed]
Pubchem: 155526778

No compound-protein relationship available.

Structure

SMILES: c1cccc2[nH]c(c3c12)c4n(CC3)c(=O)c5c(c4)cco5

Level: 0

Mol. Weight: 320.35 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.6
Plasma Protein Binding
62.87
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
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.9
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.87
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.41
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.16
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
-0.69
Rat (Acute)
3.21
Rat (Chronic Oral)
1.84
Fathead Minnow
4.73
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
477.08
Hydration Free Energy
-10.26
Log(D) at pH=7.4
2.2
Log(P)
2.4
Log S
-4.61
Log(Vapor Pressure)
-11.13
Melting Point
329.92
pKa Acid
11.22
pKa Basic
6.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9582
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9345
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9157
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9115
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.9073
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8980
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8884
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8816
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8785
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8784
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8736
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 4 0.8712
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8680
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8673
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8618
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8592
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8524
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8513
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8436
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8330
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.8325
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8301
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8249
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8231
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8223
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8217
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8166
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8146
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8145
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8123
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.8121
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8094
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8093
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8064
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.8058
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8048
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.8031
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8026
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8017
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8000
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7934
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7921
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7902
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7871
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7852
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7815
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7811
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7810
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7784
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7747
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7731
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7729
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7724
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7719
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7713
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7706
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7695
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7683
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7676
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7675
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7673
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7672
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7658
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7648
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7638
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7635
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7630
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7624
Sterol 14-alpha demethylase Q7Z1V1 CP51_TRYCC Trypanosoma cruzi 4 0.7613
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7613
Retinoic acid receptor beta P10826 RARB_HUMAN Homo sapiens 4 0.7606
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7585
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7577
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7565
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7564
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7506
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7506
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7505
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7500
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7499
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7494
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7490
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7475
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7464
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7436
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7436
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7432
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7432
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.7411
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7406
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 4 0.7394
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7392
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7376
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7374
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 4 0.7373
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7353
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7351
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7346
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7346
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7336
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7329
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7329
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7328
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7320
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7319
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7315
Bcl-2-like protein 1 Q07817 B2CL1_HUMAN Homo sapiens 3 0.7310
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7298
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7289
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7275
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7266
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7265
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7258
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7251
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7250
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7248
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7240
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7233
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7208
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7194
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7193
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7190
Carbonic anhydrase 13 Q8N1Q1 CAH13_HUMAN Homo sapiens 3 0.7186
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7184
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7180
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7172
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7167
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7155
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7152
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7150
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7148
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7147
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7144
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7140
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7132
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7120
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7117
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7107
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7105
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7100
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7099
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7095
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7095
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7082
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7081
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7073
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7062
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7062
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7062
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7058
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7056
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7056
Glycylpeptide N-tetradecanoyltransferase A5K1A2 A5K1A2_PLAVS Plasmodium vivax 3 0.7044
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7044
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.7026
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7024
Metallo-beta-lactamase type 2 P25910 BLAB_BACFG Bacteroides fragilis 3 0.7017
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7015
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7005
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7004

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