2-hydroxy-8-prenylbiochanin A - Compound Card

2-hydroxy-8-prenylbiochanin A

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2-hydroxy-8-prenylbiochanin A

Structure
Zoomed Structure
  • Family: Animalia - Apidae
  • Kingdom: Animalia
  • Class: Flavonoid
    • Subclass: Isoflavonoid
Canonical Smiles COc1ccc(cc1)c1c(O)oc2c(c1=O)c(O)cc(c2CC=C(C)C)O
InChI InChI=1S/C21H20O6/c1-11(2)4-9-14-15(22)10-16(23)18-19(24)17(21(25)27-20(14)18)12-5-7-13(26-3)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3
InChIKey FIPNHIGIKDYIFU-UHFFFAOYSA-N
Formula C21H20O6
HBA 6
HBD 3
MW 368.39
Rotatable Bonds 4
TPSA 100.13
LogP 4.09
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 368.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Apis mellifera Apidae Animalia —

Showing of synonyms

  • Tamfu AN, Sawalda M, et al. (2020). A new isoflavonol and other constituents from Cameroonian propolis and evaluation of their anti-inflammatory, antifungal and antioxidant potential.. Saudi journal of biological sciences,2020, 27(6), 1659-1666. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 368.39 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 368.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 368.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.98
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.350
Plasma Protein Binding
90.85
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
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.020
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.250
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.020
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.260
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-0.920
Rat (Acute)
2.330
Rat (Chronic Oral)
3.020
Fathead Minnow
5.120
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
475.350
Hydration Free Energy
-9.800
Log(D) at pH=7.4
3.080
Log(P)
4.88
Log S
-5.9
Log(Vapor Pressure)
-8.5
Melting Point
188.12
pKa Acid
8.0
pKa Basic
5.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9428
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 5 0.9393
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9121
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9043
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9019
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9012
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8905
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8852
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8715
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8569
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.8559
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8445
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8439
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8414
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8364
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8345
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8330
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8319
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8313
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8300
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.8293
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8280
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8272
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8178
UDP-N-acetylglucosamine 1-carboxyvinyltransferase P33038 MURA_ENTCC Enterobacter cloacae subsp. cloacae 3 0.8062
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8045
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8039
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8016
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7985
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 4 0.7970
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 4 0.7950
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7930
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7905
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7901
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7887
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7875
Flavonoid 3-O-glucosyltransferase A6XNC6 UGFGT_MEDTR Medicago truncatula 3 0.7871
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7868
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7853
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7847
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7843
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7830
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7810
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7809
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7792
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7774
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7774
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7736
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7732
Beta-ketoacyl-[acyl-carrier-protein] synthase III Q820T1 FABH_ENTFA Enterococcus faecalis 3 0.7676
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7662
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7647
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7594
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7586
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7563
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7555
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7551
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7540
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7537
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7520
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7493
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7474
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7469
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7444
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7440
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7433
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7422
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7422
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7397
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7394
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7374
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7374
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7351
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7344
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7334
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7324
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7322
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7322
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7310
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7304
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7294
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7286
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7282
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7282
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 2 0.7279
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7277
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7276
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7268
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7268
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7261
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7250
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7249
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7241
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7226
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7221
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7218
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7216
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7214
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7207
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7206
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7204
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7193
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7180
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7179
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7173
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7170
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7159
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7155
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7148
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7142
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7142
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7122
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7118
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7116
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7107
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.7100
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7093
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7081
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7062
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7058
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7052
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7052
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7035
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7035
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7032
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7026
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7024
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 4 0.7014
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7013
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7008
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7007
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7003

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