4,2',4'-trihydoxy-5,3'-diprenylchalcone - Compound Card

4,2',4'-trihydoxy-5,3'-diprenylchalcone

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4,2',4'-trihydoxy-5,3'-diprenylchalcone

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles CC(=CCc1cc(C(=O)/C=C/c2ccc(cc2)O)c(c(c1O)CC=C(C)C)O)C
InChI InChI=1S/C25H28O4/c1-16(2)5-10-19-15-22(25(29)21(24(19)28)13-6-17(3)4)23(27)14-9-18-7-11-20(26)12-8-18/h5-9,11-12,14-15,26,28-29H,10,13H2,1-4H3/b14-9+
InChIKey RWWHVUOFLZULHS-NTEUORMPSA-N
Formula C25H28O4
HBA 4
HBD 3
MW 392.5
Rotatable Bonds 7
TPSA 77.76
LogP 5.72
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 392.2
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: 11176827
Nmrshiftdb2: 70108657

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 392.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 392.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.78
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.95
Plasma Protein Binding
59.33
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.72
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.84
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.33
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3.83
Rat (Acute)
1.85
Rat (Chronic Oral)
2.96
Fathead Minnow
5.42
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
475.57
Hydration Free Energy
-6.66
Log(D) at pH=7.4
4.5
Log(P)
6.98
Log S
-6.42
Log(Vapor Pressure)
-8.75
Melting Point
161.84
pKa Acid
8.46
pKa Basic
8.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9520
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9488
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.9348
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9237
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9226
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9215
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.8994
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8932
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8864
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8814
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8737
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.8659
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8574
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8531
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8482
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.8367
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.8291
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8283
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8273
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8258
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8206
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.8159
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8147
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8126
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8098
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8094
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8089
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8080
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.8078
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8059
Subunit alpha of sarocosine oxidase Q50LF0 Q50LF0_9CORY Corynebacterium sp. U-96 4 0.8044
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8025
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8018
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8016
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7995
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7994
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7910
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7899
Isoliquiritigenin 2'-O-methyltransferase P93324 CHOMT_MEDSA Medicago sativa 4 0.7864
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7863
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7839
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7831
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7780
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7777
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7760
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7735
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7707
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7667
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7588
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7556
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 4 0.7548
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7537
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7531
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7509
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7504
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7469
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7450
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7441
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7420
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7413
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7395
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7392
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7388
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7386
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7375
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7369
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7354
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7352
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7345
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7338
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7327
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7322
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7312
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7296
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7294
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7216
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7212
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7188
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7187
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7186
Putative pteridine reductase 2 Q8I814 Q8I814_TRYCR Trypanosoma cruzi 4 0.7184
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7183
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7177
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7157
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7146
Formate--tetrahydrofolate ligase Q2RM91 FTHS_MOOTA Moorella thermoacetica 2 0.7142
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7140
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7136
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7126
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7123
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7118
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7111
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7104
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7101
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7099
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7096
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7095
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7081
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7079
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7077
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7065
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7059
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7056
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7053
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7051
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7051
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7040
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7039
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7037
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7027
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7025
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7023
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7022
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7016
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7014
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7014
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7004

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