5,4'-dihydroxy-2''-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone - Compound Card

5,4'-dihydroxy-2''-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone

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5,4'-dihydroxy-2''-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles Oc1ccc(cc1)C1COc2c(C1=O)c(O)cc1c2OC(C1)C(O)(C)C
InChI InChI=1S/C20H20O6/c1-20(2,24)15-8-11-7-14(22)16-17(23)13(9-25-19(16)18(11)26-15)10-3-5-12(21)6-4-10/h3-7,13,15,21-22,24H,8-9H2,1-2H3
InChIKey ZZWSLVGHLJEOCI-UHFFFAOYSA-N
Formula C20H20O6
HBA 6
HBD 3
MW 356.37
Rotatable Bonds 2
TPSA 96.22
LogP 2.53
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 356.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Desmodium uncinatum Leguminosae/Fabaceae Plantae 225101

Showing of synonyms

  • Tsafack BT, Ponou BK, et al. (2017). Integracide K: A New Tetracyclic Triterpenoid from Desmodium uncinatum (Jacq.) DC. (Fabaceae. Natural Product Sciences 2017, 23(2), 113-118. [View]

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)c3c(cc2)C(=O)C(CO3)c4ccccc4

Level: 1

Mol. Weight: 356.37 g/mol

Structure

SMILES: C1COc(c12)c3c(cc2)C(=O)CCO3

Level: 0

Mol. Weight: 356.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 356.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.730
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.990
Plasma Protein Binding
45.6
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-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
12.260
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.850
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.470
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.590
Micronucleos
Toxic
NR-AhR
Toxic
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
-0.030
Rat (Acute)
2.330
Rat (Chronic Oral)
2.320
Fathead Minnow
4.530
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
438.030
Hydration Free Energy
-8.920
Log(D) at pH=7.4
2.070
Log(P)
2.85
Log S
-4.01
Log(Vapor Pressure)
-8.82
Melting Point
223.15
pKa Acid
7.41
pKa Basic
4.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9498
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.9476
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9263
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.9157
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8876
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8864
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 4 0.8837
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8717
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8646
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8509
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8426
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8162
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8043
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8038
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 4 0.8016
Beta-2-microglobulin P61769 B2MG_HUMAN Homo sapiens 3 0.7966
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7907
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7878
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7750
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7737
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7705
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7691
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7627
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7620
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7595
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7591
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7575
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7525
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7376
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7348
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7341
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7332
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7322
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7285
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein Q5SHN1 Q5SHN1_THET8 Thermus thermophilus 3 0.7264
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7260
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7238
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7177
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7168
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7151
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7080
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7078
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7049

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