6,8-diprenylkaempferol - Compound Card

6,8-diprenylkaempferol

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6,8-diprenylkaempferol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles CC(=CCc1c(O)c(CC=C(C)C)c(c2c1oc(c1ccc(cc1)O)c(c2=O)O)O)C
InChI InChI=1S/C25H26O6/c1-13(2)5-11-17-20(27)18(12-6-14(3)4)25-19(21(17)28)22(29)23(30)24(31-25)15-7-9-16(26)10-8-15/h5-10,26-28,30H,11-12H2,1-4H3
InChIKey HKKPHUAEOHCSKC-UHFFFAOYSA-N
Formula C25H26O6
HBA 6
HBD 4
MW 422.48
Rotatable Bonds 5
TPSA 111.13
LogP 5.3
Number Rings 3
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 422.17
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Macaranga hurifolia Euphorbiaceae Plantae 396461

Showing of synonyms

  • Pagna JI M, Awazi T, et al. (2022). Antibacterial flavonoids from the fruits of Macaranga hurifolia.. Journal of Asian natural products research,2022, 24(11), 1041-1051. [View] [PubMed]
Pubchem: 1849
Nmrshiftdb2: 60055307

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 422.48 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 422.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 422.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.49
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.98
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.13
Plasma Protein Binding
84.94
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
4.15
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.22
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.69
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
-26.1
Rat (Acute)
2.38
Rat (Chronic Oral)
2.88
Fathead Minnow
5.34
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
529.62
Hydration Free Energy
-6.32
Log(D) at pH=7.4
3.3
Log(P)
5.92
Log S
-6.0
Log(Vapor Pressure)
-9.4
Melting Point
203.72
pKa Acid
6.31
pKa Basic
6.79
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 0.9595
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9362
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9098
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.8996
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8987
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8812
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8715
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8697
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8578
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8569
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8529
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8487
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8470
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8456
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8455
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8450
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8289
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8278
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8273
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8145
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8079
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8051
Cyclin-dependent kinase 5 Q00535 CDK5_HUMAN Homo sapiens 5 0.8009
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7966
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7882
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7853
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7821
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7819
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7743
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 5 0.7701
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7616
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7606
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7598
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7595
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7571
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7569
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7552
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7546
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7545
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7544
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7538
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7538
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7531
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7512
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7486
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7484
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7481
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7440
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7406
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7370
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7363
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7356
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7353
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7324
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7319
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7302
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7300
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7286
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7278
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7274
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7272
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7270
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7240
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7231
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7225
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.7217
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7187
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7183
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7171
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7146
Putative secreted protein C9Z6T8 C9Z6T8_STRSW Streptomyces scabiei 4 0.7120
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7120
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7114
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7093
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7092
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7089
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7050
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7037
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7032
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7029
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7028
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7025

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