3,3',5,5',7-pentahydroxyflavanone - Compound Card

3,3',5,5',7-pentahydroxyflavanone

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3,3',5,5',7-pentahydroxyflavanone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Favanol Aglycone
Canonical Smiles Oc1cc(O)cc(c1)C1Oc2cc(O)cc(c2C(=O)C1O)O
InChI InChI=1S/C15H12O7/c16-7-1-6(2-8(17)3-7)15-14(21)13(20)12-10(19)4-9(18)5-11(12)22-15/h1-5,14-19,21H
InChIKey SRHDEHLQIMAWNV-UHFFFAOYSA-N
Formula C15H12O7
HBA 7
HBD 5
MW 304.25
Rotatable Bonds 1
TPSA 127.45
LogP 1.19
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.13
Exact Mass 304.06
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Silybum marianum Asteraceae Plantae 92921

Showing of synonyms

  • Elwekeel A, Elfishway A, et al. (2012). Enhanced accumulation of flavonolignans in Silybum marianum cultured roots by methyl jasmonate. Phytochemistry Letters,2012,5,393-396. [View]
Pubchem: 25073455
Nmrshiftdb2: 70073683

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 304.25 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 304.25 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 304.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.29
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.29
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.72
Plasma Protein Binding
55.55
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
Non-Substrate
CYP 2C9 Inhibitor
Non-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
11.91
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.9
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.67
Micronucleos
Toxic
NR-AhR
Toxic
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
3.03
Rat (Acute)
2.3
Rat (Chronic Oral)
3.4
Fathead Minnow
3.94
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
475.5
Hydration Free Energy
-10.77
Log(D) at pH=7.4
1.38
Log(P)
1.2
Log S
-3.16
Log(Vapor Pressure)
-7.4
Melting Point
249.98
pKa Acid
5.94
pKa Basic
5.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9164
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9164
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8534
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8534
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8502
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8502
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8335
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8335
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8321
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8321
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8240
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8240
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8205
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8205
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8156
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8156
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8096
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8096
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8018
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8018
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7940
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7940
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7935
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7935
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7904
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7904
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7846
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7846
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7826
Dihydrofolate reductase P22906 DYR_CANAX Candida albicans 4 0.7826
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7785
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7785
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7760
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7760
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7722
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7722
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7676
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7676
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7665
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7665
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 5 0.7661
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 5 0.7661
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7635
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7635
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7615
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7615
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7592
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7592
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7570
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7570
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7565
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7565
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7539
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7539
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7515
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7515
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7509
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 4 0.7509
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7452
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7452
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7448
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7448
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7426
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7426
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7419
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7419
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7369
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7369
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7367
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7367
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7365
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7365
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7288
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7288
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7240
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7240
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7237
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7237
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7226
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7226
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7217
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7217
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7207
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7207
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7205
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 6 0.7205
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7197
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7197
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7189
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7189
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7123
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7123
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7094
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7094
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7080
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7080
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7044
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7044
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7027
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7027

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