5,4'-dihydroxy-6'',6''-dimethylchromano-(7,6,2'',3'')-flavone - Compound Card

5,4'-dihydroxy-6'',6''-dimethylchromano-(7,6,2'',3'')-flavone

Select a section from the left sidebar

5,4'-dihydroxy-6'',6''-dimethylchromano-(7,6,2'',3'')-flavone

Structure
Zoomed Structure
  • Family: Plantae - Moraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Prenylated Flavone
Canonical Smiles Oc1ccc(cc1)c1cc(=O)c2c(o1)cc1c(c2O)CCC(O1)(C)C
InChI InChI=1S/C20H18O5/c1-20(2)8-7-13-16(25-20)10-17-18(19(13)23)14(22)9-15(24-17)11-3-5-12(21)6-4-11/h3-6,9-10,21,23H,7-8H2,1-2H3
InChIKey NIZDRFCYACILLC-UHFFFAOYSA-N
Formula C20H18O5
HBA 5
HBD 2
MW 338.36
Rotatable Bonds 1
TPSA 79.9
LogP 3.97
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 338.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Dorstenia kameruniana Moraceae Plantae 984812
2 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]
  • 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: 15389226
Nmrshiftdb2: 70009215

No compound-protein relationship available.

Structure

SMILES: O1CCCc(c2)c1cc(c23)oc(cc3=O)-c4ccccc4

Level: 1

Mol. Weight: 338.36 g/mol

Structure

SMILES: O=c1ccoc(c12)cc3c(c2)CCCO3

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)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.800
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.060
Plasma Protein Binding
81.17
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.320
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.830
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.360
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.200
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
2.430
Rat (Acute)
2.510
Rat (Chronic Oral)
1.910
Fathead Minnow
4.700
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
478.890
Hydration Free Energy
-11.420
Log(D) at pH=7.4
4.360
Log(P)
5.19
Log S
-5.63
Log(Vapor Pressure)
-9.32
Melting Point
280.53
pKa Acid
7.93
pKa Basic
5.33
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 0.9795
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9502
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9487
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9012
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.8985
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8898
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8698
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8639
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8592
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8497
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8357
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8277
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8251
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8175
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8095
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8090
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8062
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7992
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7928
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7839
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7825
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7748
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7744
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7703
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7655
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7639
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7637
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7579
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7549
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7537
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7536
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7526
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7472
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7435
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7420
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7408
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7351
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7342
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7340
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7325
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7276
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7249
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7246
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7245
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7182
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7154
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7149
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7097
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7075
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7066
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7046
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7042

Download SDF