6,8-diprenylaromadendrin - Compound Card

6,8-diprenylaromadendrin

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6,8-diprenylaromadendrin

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles CC(=CCc1c2O[C@H](c3ccc(cc3)O)[C@H](C(=O)c2c(c(c1O)CC=C(C)C)O)O)C
InChI InChI=1S/C25H28O6/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/h5-10,23-24,26-28,30H,11-12H2,1-4H3/t23-,24+/m0/s1
InChIKey KITBJDQJTLGBAY-BJKOFHAPSA-N
Formula C25H28O6
HBA 6
HBD 4
MW 424.49
Rotatable Bonds 5
TPSA 107.22
LogP 4.5
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 424.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Morus mesozygia Moraceae Plantae 3054370

Showing of synonyms

  • Kapche GD, Amadou D, et al. (2011). Hepatoprotective and antioxidant arylbenzofurans and flavonoids from the twigs of Morus mesozygia.. Planta medica,2011, 77(10), 1044-1047. [View] [PubMed]
Pubchem: 10025371
Nmrshiftdb2: 60055309

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 424.49 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 424.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 424.49 g/mol

Antioxidant
Hepatoprotective

Absorption

Caco-2 (logPapp)
-5.44
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.96
Plasma Protein Binding
85.59
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
9.09
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.54
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.01
Micronucleos
Toxic
NR-AhR
Safe
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
-27.87
Rat (Acute)
2.18
Rat (Chronic Oral)
3.26
Fathead Minnow
5.04
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
482.76
Hydration Free Energy
-5.67
Log(D) at pH=7.4
3.42
Log(P)
5.59
Log S
-5.32
Log(Vapor Pressure)
-9.45
Melting Point
183.16
pKa Acid
6.69
pKa Basic
6.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9384
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9304
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9034
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9026
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8812
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 5 0.8789
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8666
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8658
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8595
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8490
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8456
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8454
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8391
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8354
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8331
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8210
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8107
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 4 0.8062
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8055
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8009
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7967
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 5 0.7853
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7820
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7810
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7790
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7777
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7728
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7713
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7699
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7695
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7693
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7690
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7664
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7601
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7558
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7455
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7394
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7354
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7329
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7320
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7243
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7226
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7186
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7180
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7179
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7164
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7102
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 5 0.7100
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7087
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7072
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7069
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7067
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 4 0.7061
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7051

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