(+)-puerol A - Compound Card

(+)-puerol A

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(+)-puerol A

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Pueroside
    • Subclass: Pueroside Glycoside
Canonical Smiles Oc1ccc(cc1)CC1OC(=O)C=C1c1ccc(cc1O)O
InChI InChI=1S/C17H14O5/c18-11-3-1-10(2-4-11)7-16-14(9-17(21)22-16)13-6-5-12(19)8-15(13)20/h1-6,8-9,16,18-20H,7H2
InChIKey AYXZYYUMEUUTRQ-UHFFFAOYSA-N
Formula C17H14O5
HBA 5
HBD 3
MW 298.29
Rotatable Bonds 3
TPSA 86.99
LogP 2.35
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 298.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ononis angustissima Leguminosae/Fabaceae Plantae 672159

Showing of synonyms

  • Ghribi L, Waffo-Téguo P, et al. (2015). Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissimaL.. Bioorganic & medicinal chemistry letters, 2015, 25(18), 3825-30. [View] [PubMed]
Pubchem: 14691941
Nmrshiftdb2: 60075883

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 298.29 g/mol

Structure

SMILES: O=C1C=CC(O1)Cc2ccccc2

Level: 1

Mol. Weight: 298.29 g/mol

Structure

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 298.29 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 298.29 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 298.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.870
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.750
Plasma Protein Binding
28.8
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.460
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.970
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.560
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.170
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
3.400
Rat (Acute)
1.980
Rat (Chronic Oral)
2.210
Fathead Minnow
4.420
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
437.570
Hydration Free Energy
-11.630
Log(D) at pH=7.4
2.450
Log(P)
1.52
Log S
-2.35
Log(Vapor Pressure)
-8.63
Melting Point
241.69
pKa Acid
7.84
pKa Basic
6.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9331
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9290
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9256
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9243
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9199
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9132
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9106
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9033
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8974
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8967
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8889
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8886
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8840
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8790
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8788
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8674
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8572
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8511
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8455
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8450
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8438
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8367
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8358
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8322
Beta-adrenergic receptor kinase 1 P25098 ARBK1_HUMAN Homo sapiens 3 0.8308
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.8299
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8299
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8279
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8239
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8236
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8193
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8129
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8104
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8095
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8077
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7985
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7960
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7886
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7886
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7874
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7795
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7778
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7774
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7764
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7744
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7742
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7733
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7717
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7713
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7713
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7712
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7710
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7710
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7704
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7672
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7649
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7647
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.7636
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7632
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7620
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7606
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7589
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7576
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7553
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7544
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7535
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7535
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7520
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 3 0.7509
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.7501
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7482
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7481
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7475
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7465
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7464
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7459
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7453
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7447
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7447
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7438
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7434
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7432
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7425
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7411
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7407
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7400
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 3 0.7393
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7393
Subunit alpha of sarocosine oxidase Q50LF0 Q50LF0_9CORY Corynebacterium sp. U-96 3 0.7379
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7366
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7366
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7356
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.7346
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7340
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7337
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7336
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7329
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 4 0.7320
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7319
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7319
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7317
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7310
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7303
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7302
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7293
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 4 0.7282
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 4 0.7280
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 4 0.7277
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7262
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7262
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7254
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7254
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7253
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7249
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7234
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7232
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7224
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7216
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7216
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7215
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7204
Protein RecA Q59560 RECA_MYCS2 Mycolicibacterium smegmatis155) 3 0.7182
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7181
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7175
Ribosomal RNA large subunit methyltransferase H P0C1V0 RLMH_STAAU Staphylococcus aureus 3 0.7160
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7155
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7147
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7147
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7143
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7140
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7140
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7132
RNA 2'-O ribose methyltransferase Q5SLL8 Q5SLL8_THET8 Thermus thermophilus 3 0.7129
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7128
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7128
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7127
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7123
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7118
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7115
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7114
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 4 0.7094
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7093
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7089
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7082
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7078
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7075
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7073
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7071
Glucose-1-phosphate thymidylyltransferase P26393 RMLA_SALTY Salmonella typhimurium 3 0.7068
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7065
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7045
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7041
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7039
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7036
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7033
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7030
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7028
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7025
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7023
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7023
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7020
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7018
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7014
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7005

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