Latonduine B methyl ester - Compound Card

Latonduine B methyl ester

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Latonduine B methyl ester

Structure
Zoomed Structure
  • Family: Animalia - Dictyonellidae
  • Kingdom: Animalia
  • Class: Alkaloid
Canonical Smiles COC(=O)c1nc(N)nc2c1c1c(Br)c([nH]c1C(=O)NC2)Br
InChI InChI=1S/C12H9Br2N5O3/c1-22-11(21)8-4-3(17-12(15)19-8)2-16-10(20)7-5(4)6(13)9(14)18-7/h18H,2H2,1H3,(H,16,20)(H2,15,17,19)
InChIKey SFCMPVWUVZLOFH-UHFFFAOYSA-N
Formula C12H9Br2N5O3
HBA 6
HBD 3
MW 431.04
Rotatable Bonds 1
TPSA 122.99
LogP 1.61
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 428.91
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Stylissa species Dictyonellidae Animalia 237127

Showing of synonyms

  • Fouad MA, Debbab A, et al. (2012). New bioactive alkaloids from the marine sponge Stylissa sp.. Tetrahedron,2012,68,10176-10179. [View]
Pubchem: 25168132
Nmrshiftdb2: 80011855

No compound-protein relationship available.

Structure

SMILES: c1c[nH]c(c12)C(=O)NCc3c2cncn3

Level: 0

Mol. Weight: 431.04 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-5.35
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.020
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
53.12
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
4.670
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.090
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.230
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.100
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
3.530
Rat (Acute)
1.940
Rat (Chronic Oral)
2.020
Fathead Minnow
4.250
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
485.690
Hydration Free Energy
-13.140
Log(D) at pH=7.4
2.060
Log(P)
1.0
Log S
-4.71
Log(Vapor Pressure)
-9.61
Melting Point
342.14
pKa Acid
7.27
pKa Basic
5.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9411
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9411
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.9405
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.9405
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.9228
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.9228
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9146
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9146
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.9087
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.9087
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9024
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9024
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8934
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8934
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8814
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8814
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8739
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8739
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8609
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8609
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8581
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8581
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8555
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8555
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8438
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8438
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8414
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8414
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8384
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8384
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.8334
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.8334
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8303
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8303
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8278
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8278
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8153
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8153
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8109
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8109
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8092
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8092
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.8088
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.8088
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8066
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.8066
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7994
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7994
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7947
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7947
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7902
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7902
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7878
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7878
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7853
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7853
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7826
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7826
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7823
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7823
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7769
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7769
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7752
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7752
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7713
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7713
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7704
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7704
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7609
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7609
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7580
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7580
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7573
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7573
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7552
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7552
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7511
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7511
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7506
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7506
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7505
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7505
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7498
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7498
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7488
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7488
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7470
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7470
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7458
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7458
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7430
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7430
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7401
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7401
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7386
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7386
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7367
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7367
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7362
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7362
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7343
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7343
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7331
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7331
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7318
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7318
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7314
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7314
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7300
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7300
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7300
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7300
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7293
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7293
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7280
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7280
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7270
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7270
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7259
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7259
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7254
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7254
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7249
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7249
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7240
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7240
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7229
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7229
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7216
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7216
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7202
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7202
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 2 0.7200
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 2 0.7200
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7192
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7192
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7190
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7190
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7178
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7178
Glutamate receptor ionotropic, NMDA 1 P35439 NMDZ1_RAT Rattus norvegicus 4 0.7177
Glutamate receptor ionotropic, NMDA 1 P35439 NMDZ1_RAT Rattus norvegicus 4 0.7177
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7173
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7173
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7169
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7169
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7168
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7168
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7167
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7167
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7156
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7156
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7109
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7109
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7109
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7109
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7106
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7106
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7106
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7106
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 2 0.7105
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 2 0.7105
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 2 0.7099
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 2 0.7099
Ribonucleoside-diphosphate reductase 2 subunit alpha Q08698 RIR3_SALTY Salmonella typhimurium 2 0.7075
Ribonucleoside-diphosphate reductase 2 subunit alpha Q08698 RIR3_SALTY Salmonella typhimurium 2 0.7075
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7072
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7072
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7066
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7066
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7056
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7056
Pyruvate dehydrogenase [ubiquinone] P07003 POXB_ECOLI Escherichia coli 3 0.7054
Pyruvate dehydrogenase [ubiquinone] P07003 POXB_ECOLI Escherichia coli 3 0.7054
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7048
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7048
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7028
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7028
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7022
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7022

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