Penicolinate A - Compound Card

Penicolinate A

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Penicolinate A

Structure
Zoomed Structure
  • Family: Fungi - Bionectriaceae
  • Kingdom: Fungi
  • Class: Pyridinemonocarboxylic Acid
    • Subclass: Bis-Picolinic Ester
Canonical Smiles COC(=O)c1ccc(cn1)CCCCCCCCCCc1ccc(nc1)C(=O)OC
InChI InChI=1S/C24H32N2O4/c1-29-23(27)21-15-13-19(17-25-21)11-9-7-5-3-4-6-8-10-12-20-14-16-22(26-18-20)24(28)30-2/h13-18H,3-12H2,1-2H3
InChIKey KQNPVQGFUTVYPP-UHFFFAOYSA-N
Formula C24H32N2O4
HBA 6
HBD 0
MW 412.53
Rotatable Bonds 13
TPSA 78.38
LogP 4.96
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 412.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bionectria sp. Bionectriaceae Fungi —

Showing of synonyms

  • Kamdem RST, Wang H, et al. (2018). Induction of new metabolites from the endophytic fungus Bionectria sp. through bacterial co-culture.. Fitoterapia,2018, 124, 132-136. [View] [PubMed]
Pubchem: 71521891
Nmrshiftdb2: 80006640

No compound-protein relationship available.

Structure

SMILES: c1ncccc1CCCCCCCCCCc2cccnc2

Level: 1

Mol. Weight: 412.53 g/mol

Structure

SMILES: c1ccncc1

Level: 0

Mol. Weight: 412.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.490
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.510
Plasma Protein Binding
37.24
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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.840
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.190
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.200
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.820
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-23.870
Rat (Acute)
2.010
Rat (Chronic Oral)
2.290
Fathead Minnow
4.520
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
437.420
Hydration Free Energy
-4.400
Log(D) at pH=7.4
5.290
Log(P)
5.04
Log S
-3.91
Log(Vapor Pressure)
-8.34
Melting Point
90.06
pKa Acid
8.97
pKa Basic
4.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8822
Insulin-like growth factor 1 receptor P08069 IGF1R_HUMAN Homo sapiens 3 0.8625
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8364
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8339
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8197
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.7919
Protease O09893 O09893_9HIV1 Human immunodeficiency virus 1 3 0.7883
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7860
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7827
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7783
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7773
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7764
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7751
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7724
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7722
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7704
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7692
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7664
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7649
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7644
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 4 0.7617
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7614
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7608
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7606
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7604
UDP-3-O-acyl-N-acetylglucosamine deacetylase O67648 LPXC_AQUAE Aquifex aeolicus 2 0.7564
Prostaglandin F2a synthase Q8I6L9 Q8I6L9_TRYCR Trypanosoma cruzi 2 0.7560
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7552
Cyclic GMP-AMP synthase Q8C6L5 CGAS_MOUSE Mus musculus 3 0.7551
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7549
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7543
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7541
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 3 0.7522
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7503
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7501
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7499
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7490
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7489
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7484
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 2 0.7481
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7473
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7471
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7468
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7468
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7462
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7450
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7438
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 2 0.7437
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7431
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7431
Lethal factor P15917 LEF_BACAN Bacillus anthracis 2 0.7427
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7425
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7423
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7418
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7417
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7414
Putative FAD-dependent oxygenase EncM Q9KHK2 Q9KHK2_9ACTN Streptomyces maritimus 2 0.7409
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7409
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 2 0.7405
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7402
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7396
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7388
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7382
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7382
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7379
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7365
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 2 0.7346
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7341
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7341
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7339
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 2 0.7338
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7334
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 2 0.7334
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7330
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7325
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7320
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7314
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7312
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7310
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7307
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7303
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 2 0.7301
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7301
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7300
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7292
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7289
Gag-Pol polyprotein P04587 POL_HV1B5 Human immunodeficiency virus type 1 group M subtype B 3 0.7287
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 3 0.7285
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7277
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7277
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7277
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 2 0.7272
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7270
VioE domain-containing protein Q7NSZ5 Q7NSZ5_CHRVO Chromobacterium violaceum 2 0.7263
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7255
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7251
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7249
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7245
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 2 0.7241
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7240
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7238
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7233
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7226
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7223
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7221
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7218
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7207
Alpha/beta hydrolase fold A5VAT9 A5VAT9_SPHWW Sphingomonas wittichii 2 0.7203
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 2 0.7203
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7201
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7194
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7194
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 2 0.7193
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7192
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7189
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 2 0.7188
L-lactate dehydrogenase (cytochrome) P00175 CYB2_YEAST Saccharomyces cerevisiae 2 0.7188
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7188
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7183
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7178
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7176
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7174
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7171
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7170
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7164
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7163
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7160
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7160
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7152
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7151
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7148
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7145
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 2 0.7140
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 2 0.7137
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7136
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 2 0.7122
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7110
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7100
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 2 0.7098
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7096
Protein mono-ADP-ribosyltransferase PARP14 Q460N5 PAR14_HUMAN Homo sapiens 2 0.7095
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7090
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 2 0.7082
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7082
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7082
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7080
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7077
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 2 0.7071
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7069
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7068
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7067
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7062
Alanine aminotransferase Q9P9M8 Q9P9M8_9EURY Pyrococcus furiosus 2 0.7048
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7040
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 2 0.7033
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 2 0.7030
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 2 0.7030
Protein mono-ADP-ribosyltransferase PARP10 Q53GL7 PAR10_HUMAN Homo sapiens 2 0.7029
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7027
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7026
Proline iminopeptidase O32449 PIP_SERMA Serratia marcescens 2 0.7023
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 2 0.7019
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7018
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7009
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7007
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7004

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