4,2',4'-trihydoxy-3'-prenylchalcone - Compound Card

4,2',4'-trihydoxy-3'-prenylchalcone

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4,2',4'-trihydoxy-3'-prenylchalcone

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles C/C(=C/Cc1c(O)cc(c2c1oc1c(O)cccc1c2=O)O)/CCC=C(C)C
InChI InChI=1S/C23H24O5/c1-13(2)6-4-7-14(3)10-11-15-18(25)12-19(26)20-21(27)16-8-5-9-17(24)22(16)28-23(15)20/h5-6,8-10,12,24-26H,4,7,11H2,1-3H3/b14-10-
InChIKey PCKHKINJZFNYEO-UVTDQMKNSA-N
Formula C23H24O5
HBA 5
HBD 3
MW 380.44
Rotatable Bonds 5
TPSA 90.9
LogP 5.3
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.26
Exact Mass 380.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Dorstenia barteri Moraceae Plantae 2604977

Showing of synonyms

  • Tsopmo A, Tene M, et al. (1999). A new diels-alder-type adduct flavonoid from Dorstenia barteri.. Journal of natural products,1999, 62(10), 1432-1434. [View] [PubMed]
Pubchem: 44396085
Chebi: 175010
Bindingdb: 50155422

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 380.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.0
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.31
Plasma Protein Binding
63.88
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
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.62
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.12
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.7
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.2
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3.93
Rat (Acute)
2.16
Rat (Chronic Oral)
2.84
Fathead Minnow
5.39
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
474.54
Hydration Free Energy
-8.44
Log(D) at pH=7.4
3.71
Log(P)
6.54
Log S
-6.05
Log(Vapor Pressure)
-9.13
Melting Point
156.06
pKa Acid
7.76
pKa Basic
7.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9339
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.9297
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9173
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8972
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8926
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8887
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.8870
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8737
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8698
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8678
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8636
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8627
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8600
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8551
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8519
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8518
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8503
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8460
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8397
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8334
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8307
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8288
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.8202
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8182
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8181
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8156
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8144
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8106
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8086
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8082
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8080
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8074
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8073
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8021
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7996
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7990
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7960
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7954
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7941
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7938
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.7933
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7923
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7907
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 4 0.7903
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7896
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7881
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7864
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7860
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7810
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7747
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 4 0.7731
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7726
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7725
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7693
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7675
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7667
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7665
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7657
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7635
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7615
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7581
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7576
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7571
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7571
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7558
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7537
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7528
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7510
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7500
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7493
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7483
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7476
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7466
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7464
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7464
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7447
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7446
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7443
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7442
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7434
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7429
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7429
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7427
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7405
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7401
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7401
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7399
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7398
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7397
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7362
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7308
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7299
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7293
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7292
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7289
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7289
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7261
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7256
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7250
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7236
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7235
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7218
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7209
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7196
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7196
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7195
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7194
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7179
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7172
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7157
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7150
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7146
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7144
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7129
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7126
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7121
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7117
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 3 0.7116
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7101
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7085
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7079
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7077
Adenosine receptor A2a P29274 AA2AR_HUMAN Homo sapiens 4 0.7066
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7066
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7064
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7060
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7060
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7052
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7049
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7045
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7039
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7038
ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 2 Q10588 BST1_HUMAN Homo sapiens 4 0.7032
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7032
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7026
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 3 0.7026
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7024
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7021
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7018
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7013
Tyrosine-protein kinase ABL1 P00519 ABL1_HUMAN Homo sapiens 3 0.7010
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7005
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.7003
Dodecin Q5SIE3 DODEC_THET8 Thermus thermophilus 4 0.7003

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