3-debromolatonduine B methyl ester - Compound Card

3-debromolatonduine B methyl ester

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3-debromolatonduine B methyl ester

Structure
Zoomed Structure
  • Family: Dictyonellidae
  • Kingdom: Animalia
  • Class: Alkaloid
Canonical Smiles COC(=O)c1nc(N)nc2c1c1cc([nH]c1C(=O)NC2)Br
InChI InChI=1S/C12H10BrN5O3/c1-21-11(20)9-7-4-2-6(13)17-8(4)10(19)15-3-5(7)16-12(14)18-9/h2,17H,3H2,1H3,(H,15,19)(H2,14,16,18)
InChIKey BMWOCQVKJMSXMM-UHFFFAOYSA-N
Formula C12H10BrN5O3
HBA 6
HBD 3
MW 352.15
Rotatable Bonds 1
TPSA 122.99
LogP 0.85
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 351.0
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: 71496944
Nmrshiftdb2: 80011857

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 200.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.41
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.150
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.560
Plasma Protein Binding
46.85
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
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
5.000
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.390
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.160
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.210
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
3.710
Rat (Acute)
1.910
Rat (Chronic Oral)
2.090
Fathead Minnow
4.040
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
470.620
Hydration Free Energy
-14.280
Log(D) at pH=7.4
1.380
Log(P)
0.84
Log S
-4.44
Log(Vapor Pressure)
-9.32
Melting Point
332.59
pKa Acid
8.16
pKa Basic
5.77
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 0.9480
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.9480
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.9257
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.9257
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.9187
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.9187
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9072
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9072
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8924
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8924
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8824
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8824
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8676
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8676
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8660
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8660
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8623
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8623
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8602
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8602
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8477
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8477
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8368
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8368
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8337
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8337
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8275
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8275
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.8273
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.8273
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8271
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8271
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8214
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8214
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8212
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.8212
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8081
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8081
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.8045
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.8045
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8023
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8023
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.8018
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.8018
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8005
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8005
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7974
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7974
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7960
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7960
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7926
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7926
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7919
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7919
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7862
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7862
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7834
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7834
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7784
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7784
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7777
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7777
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7748
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7748
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7746
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7746
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7732
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7732
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7705
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7705
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7657
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7657
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7626
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7626
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7622
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7622
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7577
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7577
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7561
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7561
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7526
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7526
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7477
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7477
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7454
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7454
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7452
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7452
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7437
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7437
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7389
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7389
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7353
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7353
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7351
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7351
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7348
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7348
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7345
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7345
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7331
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7331
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7317
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7317
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7310
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7310
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7306
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7306
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7284
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7284
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7276
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7276
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7273
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7273
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7256
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7256
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7255
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7255
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7231
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7231
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7230
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7230
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7228
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7228
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7223
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7223
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7217
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7217
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7208
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7208
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7203
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7203
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7198
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7198
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7186
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7186
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7137
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7137
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7133
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7133
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7129
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7129
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7126
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7126
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7126
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7126
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7125
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7125
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7119
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7119
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7116
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7116
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7113
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7113
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7113
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7113
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7104
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7104
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7090
GTP 3',8-cyclase P69848 MOAA_STAA8 Staphylococcus aureus 3 0.7090
Protein translocase subunit SecA P10408 SECA_ECOLI Escherichia coli 3 0.7068
Protein translocase subunit SecA P10408 SECA_ECOLI Escherichia coli 3 0.7068
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7066
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7066
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7061
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7061
Pyruvate dehydrogenase [ubiquinone] P07003 POXB_ECOLI Escherichia coli 3 0.7054
Pyruvate dehydrogenase [ubiquinone] P07003 POXB_ECOLI Escherichia coli 3 0.7054
Glutamate receptor ionotropic, NMDA 1 P35439 NMDZ1_RAT Rattus norvegicus 4 0.7051
Glutamate receptor ionotropic, NMDA 1 P35439 NMDZ1_RAT Rattus norvegicus 4 0.7051
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7046
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7046
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7044
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7044
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7034
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7034
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7023
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7023
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7020
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7020

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