Sungucine - Compound Card

Sungucine

Select a section from the left sidebar

Sungucine

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Bisindole Alkaloid
Canonical Smiles CC=C1CN2C(CC34[C@@H]2C[C@@H]1[C@@H]1C=CC(=O)N([C@H]31)c1c4cccc1)C1=C[C@H]2[C@H]3C[C@H]4C5([C@H]2N(C1=O)c1ccccc51)CCN4CC3=CC
InChI InChI=1S/C42H42N4O2/c1-3-23-21-43-16-15-41-30-9-5-8-12-33(30)46-39(41)28(27(23)18-35(41)43)17-29(40(46)48)34-20-42-31-10-6-7-11-32(31)45-37(47)14-13-25(38(42)45)26-19-36(42)44(34)22-24(26)4-2/h3-14,17,25-28,34-36,38-39H,15-16,18-22H2,1-2H3/t25-,26-,27-,28-,34?,35-,36-,38-,39-,41?,42?/m0/s1
InChIKey VCDMHIARBYKHSB-CBYDNGFISA-N
Formula C42H42N4O2
HBA 4
HBD 0
MW 634.82
Rotatable Bonds 1
TPSA 47.1
LogP 5.51
Number Rings 12
Number Aromatic Rings 2
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 634.33
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Strychnos icaja Loganiaceae Plantae 1040889
2 Strychnos icaja Loganiaceae Plantae 1040889

Showing of synonyms

  • Tchinda A, Tamze V, et al. (2012). Alkaloids from the stem bark of Strychnos icaja. Phytochemistry Letters, 2012, 5(1), 108-113. [View]
  • 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: 189778

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1C234)N5C2C(C=CC5=O)C6C(=C)CN(C3C6)C(C4)C(C7=O)=CC(C8C(=C)CN(C9C8)CC1)C2N7c(c3C129)cccc3

Level: 1

Mol. Weight: 634.82 g/mol

Structure

SMILES: C1CN(C2C3)CC(=C)C3C(C=CC4=O)C5N4c(c6C125)cccc6

Level: 0

Mol. Weight: 634.82 g/mol

Anti-plasmodial
Antimalarial

Absorption

Caco-2 (logPapp)
-5.38
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
5.4
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1383.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.14
Plasma Protein Binding
88.58
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-35.55
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.91
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.11
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2512474.71
Rat (Acute)
3.38
Rat (Chronic Oral)
1.88
Fathead Minnow
3173.15
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
280032.69
Hydration Free Energy
-2.92
Log(D) at pH=7.4
4.24
Log(P)
4.06
Log S
-5.4
Log(Vapor Pressure)
-9138.12
Melting Point
348.93
pKa Acid
-30.28
pKa Basic
6.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9115
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.8956
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8727
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8726
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8595
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8563
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8481
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8444
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8268
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8104
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8039
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8032
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8031
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7970
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7930
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7893
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7795
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7768
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7766
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7756
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7732
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7711
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 2 0.7709
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7705
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7697
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7694
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7655
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7651
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7649
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7646
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7645
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7639
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7636
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7608
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7591
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7567
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7562
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7560
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7543
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7541
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7536
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7531
Hemolymph juvenile hormone binding protein Q9U556 Q9U556_BOMMO Bombyx mori 3 0.7507
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7488
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7464
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7464
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7454
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7443
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7428
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7420
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.7404
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7400
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7372
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7360
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7357
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7356
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7350
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7340
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7338
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7336
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7330
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7323
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7297
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 2 0.7290
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7287
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7284
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7276
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7266
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.7262
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7260
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7258
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7258
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7249
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7243
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7237
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7237
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7228
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7219
Retinol-binding protein 2 P06768 RET2_RAT Rattus norvegicus 3 0.7213
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7211
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7200
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7192
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7189
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7178
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7171
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7169
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7161
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 2 0.7152
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7149
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7148
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7143
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7142
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7141
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7140
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7138
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7136
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7132
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7130
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7095
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7089
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7071
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7066
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7058
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7057
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7055
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 2 0.7031
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7029
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7023
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7023
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7013
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7012
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7010
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7007

Download SDF