Zarzissine - Compound Card

Zarzissine

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Zarzissine

Structure
Zoomed Structure
  • Family: Animalia - Anchinoidae
  • Kingdom: Animalia
  • Class: Alkaloid
    • Subclass: Guanidine Alkaloid
Canonical Smiles Nc1nc2c([nH]1)cnnc2
InChI InChI=1S/C5H5N5/c6-5-9-3-1-7-8-2-4(3)10-5/h1-2H,(H3,6,9,10)
InChIKey BUYBPEINWQQOFV-UHFFFAOYSA-N
Formula C5H5N5
HBA 4
HBD 2
MW 135.13
Rotatable Bonds 0
TPSA 80.48
LogP -0.06
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 10
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 135.05
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anchinoe paupertas Anchinoidae Animalia

Showing of synonyms

  • Bouaicha N, Amade P, et al. (1994). Zarzissine, a new cytotoxic guanidine alkaloid from the mediterranean sponge Anchinoe paupertas. Journal of Natural Products,1994,57(10),1455-1457. [View] [PubMed]
Pubchem: 6400641
Chebi: 66501
Nmrshiftdb2: 70103046
Metabolights: MTBLC66501

No compound-protein relationship available.

Structure

SMILES: n1c[nH]c(c12)cnnc2

Level: 0

Mol. Weight: 135.13 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.260
Plasma Protein Binding
17.16
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.810
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.160
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.390
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.060
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
2.090
Rat (Acute)
2.190
Rat (Chronic Oral)
2.090
Fathead Minnow
4.920
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
386.950
Hydration Free Energy
-11.970
Log(D) at pH=7.4
-0.130
Log(P)
-0.79
Log S
-1.83
Log(Vapor Pressure)
-7.68
Melting Point
287.44
pKa Acid
8.79
pKa Basic
5.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.9474
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.9474
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.9444
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.9444
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.8884
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.8884
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8388
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8388
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.8348
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.8348
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8346
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8346
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.8221
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.8221
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8081
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8081
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8076
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8076
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8073
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8073
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8000
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8000
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7853
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7853
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7768
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7768
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7761
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7761
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7690
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7690
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7686
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7686
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7685
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7685
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7684
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7684
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7668
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI Escherichia coli 3 0.7668
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7629
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7629
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7598
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7598
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7595
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7595
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7564
tRNA-guanine(15) transglycosylase O58843 ATGT_PYRHO Pyrococcus horikoshii 3 0.7564
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7526
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7526
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7478
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7478
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7468
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7468
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7433
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7433
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7427
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7427
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7420
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7420
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7380
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7380
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7375
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7375
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7361
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7361
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7361
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7361
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 2 0.7356
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 2 0.7356
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7304
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7304
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7297
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7297
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7290
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7290
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7289
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7289
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7287
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7287
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7286
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7286
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7273
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7273
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7223
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7223
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7217
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7217
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7216
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7216
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 2 0.7214
Kallikrein-4 Q9Y5K2 KLK4_HUMAN Homo sapiens 2 0.7214
Beta-galactoside alpha-2,6-sialyltransferase 1 P15907 SIAT1_HUMAN Homo sapiens 3 0.7210
Beta-galactoside alpha-2,6-sialyltransferase 1 P15907 SIAT1_HUMAN Homo sapiens 3 0.7210
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7209
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7209
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7208
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7208
Purine nucleoside phosphorylase Q9BMI9 Q9BMI9_SCHMA Schistosoma mansoni 3 0.7195
Purine nucleoside phosphorylase Q9BMI9 Q9BMI9_SCHMA Schistosoma mansoni 3 0.7195
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7194
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7194
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7187
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7187
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7174
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7174
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7171
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7171
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7163
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7163
Toluene-4-monooxygenase system, hydroxylase component subunit alpha Q00456 TMOA_PSEME Pseudomonas mendocina 2 0.7150
Toluene-4-monooxygenase system, hydroxylase component subunit alpha Q00456 TMOA_PSEME Pseudomonas mendocina 2 0.7150
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7149
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7149
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7144
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7144
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7142
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7142
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7141
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7141
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 2 0.7130
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 2 0.7130
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7120
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7120
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7111
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7111
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7107
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7107
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7104
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7104
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7098
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7098
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7097
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7097
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7094
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7094
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7092
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7092
Probable tRNA(His) guanylyltransferase Q9NWX6 THG1_HUMAN Homo sapiens 2 0.7084
Probable tRNA(His) guanylyltransferase Q9NWX6 THG1_HUMAN Homo sapiens 2 0.7084
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7075
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7075
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7066
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7066
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7056
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7056
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7054
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7054
Glutamate receptor ionotropic, kainate 1 P22756 GRIK1_RAT Rattus norvegicus 2 0.7054
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7054
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7051
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7051
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7051
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7051
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7037
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7037
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7031
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7031
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7029
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7029
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7025
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7025
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 2 0.7024
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 2 0.7024
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7020
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7020
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7006
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7006
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7000
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7000

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