Brevifolin - Compound Card

Brevifolin

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Brevifolin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Acid
Canonical Smiles COc1cc(OC)cc(c1C(=O)C)O
InChI InChI=1S/C10H12O4/c1-6(11)10-8(12)4-7(13-2)5-9(10)14-3/h4-5,12H,1-3H3
InChIKey FBUBVLUPUDBFME-UHFFFAOYSA-N
Formula C10H12O4
HBA 4
HBD 1
MW 196.2
Rotatable Bonds 3
TPSA 55.76
LogP 1.61
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 196.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia ifranensis Asteraceae Plantae 1903206
2 Pyrethrum santolinoides Asteraceae Plantae 2072400

Showing of synonyms

  • Mahmoud AA, Ahmed AA, et al. (1994). 2,3-secogermacranolides and germacranolides from Pyrethrum santolionoides. Phytochemistry,1994,36(2),393-398. [View]
  • Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones from North African Artemisia species.. Phytochemistry,1994,37(2),477-485. [View]
CPRiL: 145296
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 196.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.4
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.240
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.460
Plasma Protein Binding
15.52
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
8.360
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.050
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.090
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.040
Micronucleos
Safe
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
3.050
Rat (Acute)
2.050
Rat (Chronic Oral)
2.290
Fathead Minnow
4.000
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
304.970
Hydration Free Energy
-9.620
Log(D) at pH=7.4
1.620
Log(P)
1.82
Log S
-2.33
Log(Vapor Pressure)
-3.82
Melting Point
64.93
pKa Acid
8.48
pKa Basic
4.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9731
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9731
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.9634
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 3 0.9634
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9598
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9598
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9511
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9511
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9419
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9419
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.9361
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.9361
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.9253
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.9253
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.8726
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.8726
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8148
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8148
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.8064
orotidine-5'-phosphate decarboxylase Q8T6J6 Q8T6J6_PLAFA Plasmodium falciparum 4 0.8064
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7962
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7962
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7788
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7788
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7776
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7776
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7756
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7756
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7733
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 3 0.7733
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7608
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7608
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7598
LysR-type regulatory protein Q7WT50 Q7WT50_9BURK Burkholderia sp. DNT 3 0.7598
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7591
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7591
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7582
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7582
Orotate phosphoribosyltransferase P08870 PYRE_SALTY Salmonella typhimurium 3 0.7561
Orotate phosphoribosyltransferase P08870 PYRE_SALTY Salmonella typhimurium 3 0.7561
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7524
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7524
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7478
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7478
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7446
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7446
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7428
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7428
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7411
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7411
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7404
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7404
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7403
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7403
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7393
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7393
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7392
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7392
Uricase Q00511 URIC_ASPFL Aspergillus flavus 3 0.7386
Uricase Q00511 URIC_ASPFL Aspergillus flavus 3 0.7386
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7357
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7357
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7354
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7354
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7330
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7330
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7330
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7330
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7329
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7329
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7301
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7301
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7296
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7296
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7295
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7295
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7291
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7291
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7282
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7282
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7273
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7273
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7271
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7271
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7256
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7256
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7228
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7228
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7210
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7210
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7209
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7209
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7208
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7208
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7205
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7205
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7200
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7200
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7198
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7198
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7189
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7189
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7176
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7176
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7173
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7173
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7168
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7168
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7167
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7167
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7164
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7164
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7164
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7164
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7145
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7145
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 2 0.7139
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 2 0.7139
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7137
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7137
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7135
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7135
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7133
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7133
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7129
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7129
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 3 0.7128
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 3 0.7128
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7111
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7111
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7108
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7108
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7107
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7107
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7089
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7089
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7078
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7078
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7075
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7075
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7056
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7056
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7052
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7052
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7041
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7041
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7036
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7036
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7035
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7035
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7034
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7034
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7026
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7026
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7005
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7005
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7004
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7004

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