Phenazine-1-carboxylic acid - Compound Card

Phenazine-1-carboxylic acid

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Phenazine-1-carboxylic acid

Structure
Zoomed Structure
  • Family: Fungi - Nectriaceae
  • Kingdom: Fungi
  • Class: Alkaloid
    • Subclass: Phenazine Alkaloid
Canonical Smiles OC(=O)c1cccc2c1nc1ccccc1n2
InChI InChI=1S/C13H8N2O2/c16-13(17)8-4-3-7-11-12(8)15-10-6-2-1-5-9(10)14-11/h1-7H,(H,16,17)
InChIKey JGCSKOVQDXEQHI-UHFFFAOYSA-N
Formula C13H8N2O2
HBA 3
HBD 1
MW 224.22
Rotatable Bonds 1
TPSA 63.08
LogP 2.48
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 224.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Fusarium tricinctum Nectriaceae Fungi 61284

Showing of synonyms

  • Moussa M, Ebrahim W, et al. (2020). Co-culture of the bacterium Pseudomonas aeruginosa with the fungus Fusarium tricinctum induces bacterial antifungal and quorum sensing signaling molecules. Phytochemistry Letters, 2020, 36, 37-41. [View]
CPRiL: 100634
Structure

SMILES: c1cccc(c12)nc3c(n2)cccc3

Level: 0

Mol. Weight: 224.22 g/mol

Antifungal

Absorption

Caco-2 (logPapp)
-4.78
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.99
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.63
Plasma Protein Binding
74.05
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
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
0.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.61
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
1.77
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
3.07
Rat (Acute)
2.13
Rat (Chronic Oral)
2.3
Fathead Minnow
4.44
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
375.88
Hydration Free Energy
-9.54
Log(D) at pH=7.4
-0.21
Log(P)
2.27
Log S
-2.23
Log(Vapor Pressure)
-6.99
Melting Point
237.4
pKa Acid
4.05
pKa Basic
2.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9715
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.9420
Thiazole tautomerase P25053 TENI_BACSU Bacillus subtilis 3 0.9296
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.9280
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9256
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.9208
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.9161
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.9062
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9024
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9013
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8995
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8957
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8880
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8844
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 3 0.8810
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8804
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8782
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8782
Stimulator of interferon genes protein Q86WV6 STING_HUMAN Homo sapiens 3 0.8736
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 3 0.8725
Albumin P35747 ALBU_HORSE Equus caballus 3 0.8718
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8675
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8664
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8626
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8600
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8582
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8560
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8546
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8543
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8523
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8517
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8494
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8420
Pentalenic acid synthase Q825I8 CYP28_STRAW Streptomyces avermitilis 3 0.8419
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8369
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.8346
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8314
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8256
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8249
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8235
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8232
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8224
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8188
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8153
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8105
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8083
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8069
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.8059
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8048
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8002
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7977
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7971
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7971
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7962
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7940
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7939
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7935
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7904
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7877
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 3 0.7855
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7829
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7809
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7790
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7768
Lipoprotein E P26093 HEL_HAEIN Haemophilus influenzae 3 0.7766
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.7764
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7763
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7748
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7719
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.7709
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7698
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7681
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7673
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7666
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 3 0.7663
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7654
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7648
1-deoxy-D-xylulose 5-phosphate reductoisomerase P9WNS1 DXR_MYCTU Mycobacterium tuberculosis 3 0.7648
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7636
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7621
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7621
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7620
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7598
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7596
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7594
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7581
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7573
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7568
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7554
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7547
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7541
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.7540
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7530
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7522
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7507
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7493
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7483
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7472
Phenylpyruvate C(3)-methyltransferase Q643C8 MPPJ_STRHY Streptomyces hygroscopicus 3 0.7472
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7440
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7435
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7434
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7433
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 2 0.7425
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7399
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7392
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7370
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7367
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7363
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7326
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7316
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7303
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7296
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7281
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7266
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7263
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7255
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7221
Cysteine synthase 1 P47998 CYSK1_ARATH Arabidopsis thaliana 3 0.7220
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7219
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7214
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7208
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7197
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7172
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7172
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7168
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 3 0.7165
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7162
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7161
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7158
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7128
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7125
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7117
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7107
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7104
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7092
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7089
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7088
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7087
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7083
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7077
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7076
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7076
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7065
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7061
Beta-1,4-galactosyltransferase 1 P08037 B4GT1_BOVIN Bos taurus 3 0.7059
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 2 0.7059
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7054
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7051
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7048
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7031
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 2 0.7014
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7013
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 2 0.7011

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