6-prenylpinocembrin benzylether - Compound Card

6-prenylpinocembrin benzylether

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6-prenylpinocembrin benzylether

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles CC(=CCc1c(O)cc2c(c1OCc1ccccc1)C(=O)CC(O2)c1ccccc1)C
InChI InChI=1S/C27H26O4/c1-18(2)13-14-21-22(28)15-25-26(27(21)30-17-19-9-5-3-6-10-19)23(29)16-24(31-25)20-11-7-4-8-12-20/h3-13,15,24,28H,14,16-17H2,1-2H3
InChIKey UVBCWADJQFLQFV-UHFFFAOYSA-N
Formula C27H26O4
HBA 4
HBD 1
MW 414.5
Rotatable Bonds 6
TPSA 55.76
LogP 6.19
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 414.18
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pseudarthria hookeri Leguminosae/Fabaceae Plantae 992776

Showing of synonyms

  • Tchamgoue J, Hafizur R, et al. (2016). Flavonoids and other constituents with insulin secretion activity from Pseudarthria hookeri. Phytochemistry Letters, 2016, 17, 181-186. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1COc2cccc(c23)OC(CC3=O)c4ccccc4

Level: 2

Mol. Weight: 414.5 g/mol

Structure

SMILES: c1ccccc1COc2cccc(c23)OCCC3=O

Level: 1

Mol. Weight: 414.5 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 414.5 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 414.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 414.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.55
Plasma Protein Binding
87.98
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.29
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.49
Micronucleos
Toxic
NR-AhR
Toxic
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
-62.5
Rat (Acute)
2.01
Rat (Chronic Oral)
2.04
Fathead Minnow
5.84
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
483.22
Hydration Free Energy
-3.31
Log(D) at pH=7.4
4.31
Log(P)
6.37
Log S
-6.23
Log(Vapor Pressure)
-9.36
Melting Point
116.02
pKa Acid
8.97
pKa Basic
6.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.9767
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9690
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.9546
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.9505
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9253
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9210
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9160
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.9062
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.9050
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.9043
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9001
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8947
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8940
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8865
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8757
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.8716
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8646
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.8612
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8601
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8552
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8531
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8467
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8407
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.8363
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8361
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8360
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8284
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8229
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8212
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8184
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8182
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8164
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8144
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8092
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8062
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8050
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8027
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7997
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7973
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7967
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7943
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7910
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7907
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7887
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7885
Protease Q5RTL1 Q5RTL1_9HIV1 Human immunodeficiency virus 1 4 0.7882
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7876
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7841
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7808
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7803
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7802
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7796
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7794
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7773
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7757
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7739
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7733
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 2 0.7718
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7710
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7695
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7692
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7684
Tissue factor P13726 TF_HUMAN Homo sapiens 3 0.7682
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7673
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7666
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7664
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7639
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7616
Polymerase acidic protein P03433 PA_I34A1 Influenza A virus 2 0.7608
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7601
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7582
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7582
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7569
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7532
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7507
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7505
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7501
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7493
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7487
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7485
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7479
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7466
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7458
Uncharacterized protein Q55S71 Q55S71_CRYNB Cryptococcus neoformans var. neoformans serotype D 3 0.7453
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7443
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7436
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7415
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7408
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.7389
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7381
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7376
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7358
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7351
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7342
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7339
Formate--tetrahydrofolate ligase Q2RM91 FTHS_MOOTA Moorella thermoacetica 2 0.7315
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7313
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 3 0.7307
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7305
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7305
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7280
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7271
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7268
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7263
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7260
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7259
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7257
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7255
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7252
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7251
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 3 0.7248
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7247
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7227
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7226
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7216
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7214
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7211
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7203
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7196
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7186
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7180
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7179
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7179
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7168
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7167
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.7157
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7154
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7144
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7140
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7131
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial Q6NVY1 HIBCH_HUMAN Homo sapiens 3 0.7130
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7125
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7117
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7115
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7111
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7104
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7102
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7097
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7092
Histidinol dehydrogenase Q8G2R2 HISX_BRUSU Brucella suis biovar 1 3 0.7088
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7088
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7085
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7084
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7083
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7070
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7059
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7056
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7048
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 2 0.7026
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7025
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7025
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7022
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7011
Tryptase alpha/beta-1 Q15661 TRYB1_HUMAN Homo sapiens 3 0.7008
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7003

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