Littorine - Compound Card

Littorine

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Littorine

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O[C@@H](C(=O)OC1C[C@@H]2CC[C@H](C1)N2C)Cc1ccccc1
InChI InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)11-15(10-13)21-17(20)16(19)9-12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16-/m1/s1
InChIKey FNRXUEYLFZLOEZ-VFSICIBPSA-N
Formula C17H23NO3
HBA 4
HBD 1
MW 289.37
Rotatable Bonds 4
TPSA 49.77
LogP 1.76
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 289.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Datura stramonium Solanaceae Plantae 4076

Showing of synonyms

  • El Bazaoui A, Bellimam MA, et al. (2011). Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS. Fitoterapia,2011,82(2),193-197. [View] [PubMed]
Pubchem: 12311316
Nmrshiftdb2: 70004772

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CC(C1)OC(=O)CCc3ccccc3

Level: 1

Mol. Weight: 289.37 g/mol

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 289.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 289.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.04
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.31
Plasma Protein Binding
51.12
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
Non-Inhibitor

Excretion

Clearance
8.68
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.28
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-2.78
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.4
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
-1.09
Rat (Acute)
2.62
Rat (Chronic Oral)
1.89
Fathead Minnow
3.93
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
345.38
Hydration Free Energy
-9.35
Log(D) at pH=7.4
0.83
Log(P)
2.04
Log S
-1.87
Log(Vapor Pressure)
-6.41
Melting Point
132.66
pKa Acid
8.24
pKa Basic
8.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.9507
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.9507
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9290
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9290
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.9288
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.9288
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 3 0.9069
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 3 0.9069
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.8955
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.8955
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8897
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8897
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8890
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8890
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8828
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8828
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8599
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8599
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.8597
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.8597
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8561
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8561
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8555
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8555
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8520
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8520
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8379
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8379
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8154
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8154
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8040
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8040
Putative FAD-dependent oxygenase EncM Q9KHK2 Q9KHK2_9ACTN Streptomyces maritimus 3 0.8000
Putative FAD-dependent oxygenase EncM Q9KHK2 Q9KHK2_9ACTN Streptomyces maritimus 3 0.8000
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7890
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7890
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7854
histone deacetylase A5H660 A5H660_SCHMA Schistosoma mansoni 3 0.7854
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7842
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7842
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7777
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7777
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7749
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7749
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7727
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7727
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7718
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7718
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7662
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7662
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7655
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7655
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7647
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7647
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7639
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7639
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7611
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7611
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7589
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7589
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7558
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7558
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7537
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7537
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7515
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7515
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 0.7514
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 0.7514
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7467
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7467
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7464
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7464
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7455
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 3 0.7455
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7444
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7444
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7431
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7431
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7381
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7381
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7370
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7370
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7353
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7353
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7332
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7332
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7328
Laminarinase Q9WXN1 Q9WXN1_THEMA Thermotoga maritima 3 0.7328
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7327
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7327
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7325
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7325
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7322
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7322
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7297
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7297
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7295
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7295
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7290
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7290
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7288
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7288
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7286
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7286
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7268
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7268
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7256
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7256
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 3 0.7252
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 3 0.7252
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7229
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7229
Tissue factor P13726 TF_HUMAN Homo sapiens 3 0.7227
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7227
Tissue factor P13726 TF_HUMAN Homo sapiens 3 0.7227
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7227
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7220
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7220
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7212
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7212
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7205
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7205
Diaminopimelate decarboxylase A1SR00 A1SR00_PSYIN Psychromonas ingrahamii 2 0.7192
Diaminopimelate decarboxylase A1SR00 A1SR00_PSYIN Psychromonas ingrahamii 2 0.7192
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7174
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7174
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7153
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7153
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7148
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7148
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7138
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7138
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7134
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7134
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7130
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7130
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7110
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7110
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7094
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7094
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7093
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7093
Bifunctional glutamate/proline--tRNA ligase P07814 SYEP_HUMAN Homo sapiens 2 0.7092
Bifunctional glutamate/proline--tRNA ligase P07814 SYEP_HUMAN Homo sapiens 2 0.7092
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7084
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7084
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7076
Adenosine 5'-monophosphoramidase HINT1 P49773 HINT1_HUMAN Homo sapiens 3 0.7076
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7069
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7069
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7065
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7065
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7060
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7060
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7059
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7059
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7056
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7056
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7032
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7032
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7031
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7031
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7027
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7027
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7024
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7024
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7023
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7023
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7023
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7023
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7010
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7010
Phosphomethylpyrimidine synthase, chloroplastic O82392 THIC_ARATH Arabidopsis thaliana 3 0.7007
Phosphomethylpyrimidine synthase, chloroplastic O82392 THIC_ARATH Arabidopsis thaliana 3 0.7007
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7003
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7003
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7003
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7003
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7001
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7001

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