Latifoliaindole A - Compound Card

Latifoliaindole A

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Latifoliaindole A

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles C/C=C(\c1cc2c3[nH]c4c(c3CCn2c(=O)c1O)cccc4)/C=O
InChI InChI=1S/C19H16N2O3/c1-2-11(10-22)14-9-16-17-13(7-8-21(16)19(24)18(14)23)12-5-3-4-6-15(12)20-17/h2-6,9-10,20,23H,7-8H2,1H3/b11-2-
InChIKey SSXJDMGJJARZQV-FUQNDXKWSA-N
Formula C19H16N2O3
HBA 4
HBD 2
MW 320.35
Rotatable Bonds 2
TPSA 75.09
LogP 2.86
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.16
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: 155520886

No compound-protein relationship available.

Structure

SMILES: c1ccc(=O)n(CC2)c1c(c2c34)[nH]c3cccc4

Level: 0

Mol. Weight: 320.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.51
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.84
Plasma Protein Binding
51.58
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
3.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.28
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.11
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.0
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
Toxic
T. Pyriformis
1.82
Rat (Acute)
2.96
Rat (Chronic Oral)
1.85
Fathead Minnow
4.81
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
470.92
Hydration Free Energy
-11.54
Log(D) at pH=7.4
1.93
Log(P)
2.38
Log S
-4.25
Log(Vapor Pressure)
-9.5
Melting Point
273.26
pKa Acid
9.28
pKa Basic
6.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 4 0.9139
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.9059
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8554
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8548
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.8299
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8293
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8201
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8192
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8186
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8169
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.8117
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8095
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8047
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.8021
Apoptosis regulator Bcl-2 P10415 BCL2_HUMAN Homo sapiens 3 0.8001
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7994
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7954
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7934
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7924
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7904
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7902
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7851
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7790
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7767
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7765
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7725
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7723
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7715
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7700
Poly [ADP-ribose] polymerase tankyrase-1 O95271 TNKS1_HUMAN Homo sapiens 3 0.7696
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7681
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7678
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7655
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7652
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7608
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7604
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7602
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7594
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7587
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7562
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7556
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7532
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 4 0.7519
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7502
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7468
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7465
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7463
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7456
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7450
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7446
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7431
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7395
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7394
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7387
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 4 0.7381
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7338
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7326
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7319
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7306
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7293
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7293
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7279
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7275
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7274
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 3 0.7256
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7252
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7199
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7189
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7180
MutT/nudix family protein Q5SJY9 Q5SJY9_THET8 Thermus thermophilus 2 0.7173
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7164
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7130
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7117
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7115
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7087
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7085
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7071
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7047
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7033

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