6-prenylpinocembrin acetate - Compound Card

6-prenylpinocembrin acetate

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6-prenylpinocembrin acetate

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles CC(=O)Oc1cc2OC(CC(=O)c2c(c1CC=C(C)C)O)c1ccccc1
InChI InChI=1S/C22H22O5/c1-13(2)9-10-16-19(26-14(3)23)12-20-21(22(16)25)17(24)11-18(27-20)15-7-5-4-6-8-15/h4-9,12,18,25H,10-11H2,1-3H3
InChIKey SLZYEUSLKLTVEI-UHFFFAOYSA-N
Formula C22H22O5
HBA 5
HBD 1
MW 366.41
Rotatable Bonds 4
TPSA 72.83
LogP 4.53
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 366.15
Number of Lipinski Rule Violations 0
# 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: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 366.41 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 366.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 366.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.55
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.31
Plasma Protein Binding
62.09
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
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
7.24
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.68
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.46
Micronucleos
Toxic
NR-AhR
Safe
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
Safe
T. Pyriformis
-1.01
Rat (Acute)
2.18
Rat (Chronic Oral)
2.46
Fathead Minnow
5.2
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
427.09
Hydration Free Energy
-7.27
Log(D) at pH=7.4
3.53
Log(P)
5.01
Log S
-5.99
Log(Vapor Pressure)
-7.98
Melting Point
125.52
pKa Acid
8.07
pKa Basic
5.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.9061
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9049
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9025
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8916
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8884
Caspase-6 P55212 CASP6_HUMAN Homo sapiens 3 0.8879
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8870
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8691
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8563
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8448
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.8432
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8367
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8221
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8163
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.8120
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8056
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7953
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7925
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7866
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7827
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7800
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7739
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7722
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7701
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7672
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7650
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7636
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7633
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7632
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7624
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7592
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7585
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7540
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7533
Phosphoribosylformylglycinamidine synthase subunit PurL Q9X0X3 PURL_THEMA Thermotoga maritima 3 0.7518
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7469
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7461
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7447
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7426
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7419
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7402
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7388
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7364
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7359
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7354
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7331
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7323
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7302
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7295
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7293
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7282
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7275
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7260
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7258
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7258
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7240
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7224
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7221
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7219
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7217
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7205
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7171
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7155
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7143
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7136
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7117
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7116
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7116
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7116
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7107
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7107
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7105
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7102
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7084
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7075
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7068
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7064
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7059
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7058
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7049
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7043
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7042
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7029
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7023
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7017
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7017
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7015
Protein claret segregational P20480 NCD_DROME Drosophila melanogaster 2 0.7015
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7010
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7006
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7006
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7003
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7001

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