6-prenylapigenin - Compound Card

6-prenylapigenin

Select a section from the left sidebar

6-prenylapigenin

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylated Flavone
Canonical Smiles CC(=CCc1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)O)C
InChI InChI=1S/C20H18O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9-10,21-22,24H,8H2,1-2H3
InChIKey VJDRSTHNWHVTNQ-UHFFFAOYSA-N
Formula C20H18O5
HBA 5
HBD 3
MW 338.36
Rotatable Bonds 3
TPSA 90.9
LogP 4.09
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 338.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dorstenia kameruniana Moraceae Plantae 984812
2 Dorstenia ciliata Moraceae Plantae 2604984
3 Dorstenia dinklagei Moraceae Plantae 2604986

Showing of synonyms

  • Ngadjui BT, Dongo E, et al. (2002). Dinklagins A, B and C: three prenylated flavonoids and other constituents from the twigs of Dorstenia dinklagei.. Phytochemistry,2002, 61(1), 99-104. [View] [PubMed]
  • Ngadjui BT, Ngameni B, et al. (2002). Prenylated and geranylated chalcones and flavones from the aerial parts of Dorstenia ciliata. Bulletin of The Chemical Society of Ethiopia, 2002, 16(2), 157-164. [View]
  • Abegaz BM, Ngadjui BT, et al. (1998). Prenylated chalcones and flavones from the leaves of dorstenia kameruniana. Phytochemistry, 1998, 49(4), 1147-1150. [View]
Pubchem: 10382485
Nmrshiftdb2: 60025914
CPRiL: 301291
Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 338.36 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 338.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 338.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.0
Plasma Protein Binding
82.52
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.01
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.64
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.3
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.68
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
2.78
Rat (Acute)
2.23
Rat (Chronic Oral)
2.55
Fathead Minnow
4.86
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
482.55
Hydration Free Energy
-12.62
Log(D) at pH=7.4
3.89
Log(P)
5.31
Log S
-5.57
Log(Vapor Pressure)
-9.08
Melting Point
246.45
pKa Acid
7.34
pKa Basic
6.77
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9794
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9491
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9488
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9258
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9204
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9182
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9115
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8929
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8889
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8889
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8889
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8836
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8787
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8703
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8688
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8647
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8627
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8610
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8603
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8526
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8523
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8477
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8354
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8343
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8334
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8329
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.8325
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8307
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8287
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.8259
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8259
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8220
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8208
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.8075
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8072
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8018
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8008
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8001
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7959
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7955
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7951
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7946
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7938
Chalcone synthase 2 P30074 CHS2_MEDSA Medicago sativa 5 0.7905
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7876
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7870
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7829
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7751
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7747
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7744
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7726
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7671
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7605
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7564
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7558
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7556
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7542
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7530
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7529
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7527
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7506
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7505
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7504
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7502
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7463
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7456
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7449
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7441
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7410
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7402
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7398
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7371
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7364
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7353
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7345
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7337
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7336
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7333
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7325
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7305
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7300
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7286
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7272
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7268
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7267
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7261
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7257
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7245
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7241
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7236
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7221
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7208
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7204
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7203
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7191
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7189
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7150
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7141
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7136
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7135
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7134
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7105
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7098
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7088
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7082
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7077
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7067
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7058
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7057
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7052
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7041
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7013
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7011
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7004
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7004
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7004
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7003

Download SDF