Guianensine - Compound Card

Guianensine

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Guianensine

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Zwitterionic Alkaloid
Canonical Smiles CCc1c[n+]2ccc3c(c2cc1C1=CN2c4ccccc4[C@]45[C@@H]2[C@H]([C@@H]1O)[C@H]1C[C@@H]5N(C/C/1=C\C(=O)O)CC4)[nH]c1c3c(OC)ccc1
InChI InChI=1S/C39H36N4O4/c1-3-21-18-41-13-11-23-34-28(8-6-10-31(34)47-2)40-36(23)30(41)16-24(21)26-20-43-29-9-5-4-7-27(29)39-12-14-42-19-22(15-33(44)45)25(17-32(39)42)35(37(26)46)38(39)43/h4-11,13,15-16,18,20,25,32,35,37-38,46H,3,12,14,17,19H2,1-2H3,(H,44,45)/p+1/b22-15+/t25-,32-,35-,37+,38-,39+/m0/s1
InChIKey BAOFYTRCQGOFJD-KOQGAJESSA-O
Formula C39H37N4O4+
HBA 5
HBD 3
MW 625.75
Rotatable Bonds 4
TPSA 93.13
LogP 5.21
Number Rings 10
Number Aromatic Rings 5
Heavy Atom Count 47
Formal Charge 1
Fraction CSP3 0.33
Exact Mass 625.28
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Strychnos guianensis Loganiaceae Plantae 1040886

Showing of synonyms

  • Frederich M, Hayette MP, et al. (1999). In vitro activities of Strychnos alkaloids and extracts against Plasmodium falciparum.. Antimicrobial agents and chemotherapy,1999, 43(9), 2328-31. [View] [PubMed]
Pubchem: 101682259

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1C234)N5C2C(C6C(=C)CN(C3C6)CC4)CC(=C5)c(c7)cc[n+](cc8)c7c9[nH]c(c1c89)cccc1

Level: 1

Mol. Weight: 625.75 g/mol

Structure

SMILES: C1CN(C2C3)CC(=C)C3C(CC=C4)C5N4c(c6C125)cccc6

Level: 0

Mol. Weight: 625.75 g/mol

Structure

SMILES: c1cccc(c1c23)[nH]c2c4[n+](cc3)cccc4

Level: 0

Mol. Weight: 625.75 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-5.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-2.23
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
456.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.4
Plasma Protein Binding
98.01
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
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.05
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-9.54
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.12
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.31
Micronucleos
Toxic
NR-AhR
Safe
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
-831860.53
Rat (Acute)
2.91
Rat (Chronic Oral)
1.61
Fathead Minnow
1055.71
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
88862.15
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.16
Log(P)
1.88
Log S
-3.52
Log(Vapor Pressure)
-2930.97
Melting Point
333.82
pKa Acid
0.39
pKa Basic
7.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9554
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9340
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9203
Renin P00797 RENI_HUMAN Homo sapiens 3 0.9124
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.9056
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8895
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8795
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.8568
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8512
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8494
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.8434
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8419
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8325
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8205
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8148
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8122
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8093
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.8022
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7917
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7909
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7908
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7902
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7888
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7878
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7862
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7861
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7802
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7764
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7741
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7738
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7720
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 3 0.7717
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7699
Enoyl-[acyl-carrier-protein] reductase [NADH] Q5NGQ3 Q5NGQ3_FRATT Francisella tularensis subsp. tularensis 3 0.7648
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7643
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7635
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7631
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7625
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7604
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7591
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7567
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7539
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7534
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7506
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7501
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7476
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7457
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7441
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7421
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7416
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7399
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7375
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7363
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7351
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7346
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.7340
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7340
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 3 0.7300
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7297
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7280
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7279
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7256
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7247
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7247
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7240
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7228
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7228
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7224
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7220
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7217
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7201
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7195
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7175
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7165
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7162
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7154
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7140
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7136
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7131
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7130
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7130
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7124
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7116
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7116
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7095
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7085
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7083
Reductase homolog Q9ZGC1 Q9ZGC1_STRCY Streptomyces cyanogenus 3 0.7081
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7070
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7065
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7061
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7061
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7061
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7057
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7056
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7054
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7049
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7043
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7042
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7042
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7041
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7039
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7030
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7017
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7015
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7015
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7013
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7012
Histone H3 P61830 H3_YEAST Saccharomyces cerevisiae 2 0.7008
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7000

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