Phloridzin - Compound Card

Phloridzin

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Phloridzin

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Chalcone
    • Subclass: Dihydrochalcone
Canonical Smiles OC[C@H]1O[C@@H](Oc2cc(O)cc(c2C(=O)CCc2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
InChIKey IOUVKUPGCMBWBT-QNDFHXLGSA-N
Formula C21H24O10
HBA 10
HBD 7
MW 436.41
Rotatable Bonds 7
TPSA 177.14
LogP -0.2
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 436.14
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Rosmarinuseriocalyx Lamiaceae Plantae

Showing of synonyms

  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
Pubchem: 6072
Kegg Ligand: C01604
Chebi: 8113
Nmrshiftdb2: 60021296
Metabolights: MTBLC8113
Drugbank: DB16771
Pdb Ligand: LN9
Bindingdb: 20875
CPRiL: 1315
Structure

SMILES: c1ccccc1CCC(=O)c2c(cccc2)OC3CCCCO3

Level: 2

Mol. Weight: 436.41 g/mol

Structure

SMILES: c1ccccc1C(=O)CCc2ccccc2

Level: 1

Mol. Weight: 436.41 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 436.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 436.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 436.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-7.0
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.480
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.760
Plasma Protein Binding
76.23
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.200
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.160
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.600
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.720
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
-35.350
Rat (Acute)
2.340
Rat (Chronic Oral)
3.900
Fathead Minnow
4.070
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
587.340
Hydration Free Energy
-7.930
Log(D) at pH=7.4
0.560
Log(P)
-0.3
Log S
-3.2
Log(Vapor Pressure)
-12.64
Melting Point
161.63
pKa Acid
4.86
pKa Basic
7.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9584
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9433
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.9410
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.9326
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.9149
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8889
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8857
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8772
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8713
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8688
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8668
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8663
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8661
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8654
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8597
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8587
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8444
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8429
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8420
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.8405
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8399
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8384
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8373
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8354
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8344
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8288
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8282
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8268
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8267
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8258
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8237
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8135
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8124
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.8056
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.8044
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8042
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8004
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7909
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7872
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7865
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7850
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7845
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7829
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7829
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7798
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7719
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7704
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7700
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7689
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7687
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7675
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7673
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7671
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7651
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7641
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7640
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7634
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7612
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7607
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7588
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7582
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7553
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7547
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7535
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7512
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1 Q15750 TAB1_HUMAN Homo sapiens 3 0.7493
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7491
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7487
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7467
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7467
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7465
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7465
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7463
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7462
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7462
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7452
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7419
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7400
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7386
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7357
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7355
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7343
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7336
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7325
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7318
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7301
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7297
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7296
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7291
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7276
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7256
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7251
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7242
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7236
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7233
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7232
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7225
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7224
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7217
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7216
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7210
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7205
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7201
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7197
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7185
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7173
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7171
Seed lectin subunit I P05045 LEC1_VIGUC Vigna unguiculata subsp. cylindrica 3 0.7169
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7158
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7152
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7150
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7149
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7148
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7146
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7134
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7124
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7108
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7107
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7104
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7098
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7089
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7087
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 2 0.7083
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7082
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7073
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7066
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7064
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7053
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7039
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 4 0.7037
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7031
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 4 0.7023
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7017
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 4 0.7016
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7016
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7009
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7004
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7004
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.7000

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