(2S)-5-hydroxy-7,8-dimethoxyflavanone - Compound Card

(2S)-5-hydroxy-7,8-dimethoxyflavanone

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(2S)-5-hydroxy-7,8-dimethoxyflavanone

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles COc1c(OC)cc(c2c1OC(c1ccccc1)C(=O)C2)O
InChI InChI=1S/C17H16O5/c1-20-14-9-12(18)11-8-13(19)15(10-6-4-3-5-7-10)22-16(11)17(14)21-2/h3-7,9,15,18H,8H2,1-2H3
InChIKey KPUNBNWFRBNTKV-UHFFFAOYSA-N
Formula C17H16O5
HBA 5
HBD 1
MW 300.31
Rotatable Bonds 3
TPSA 64.99
LogP 2.65
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 300.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Oxyanthus unilocularis Annonaceae Plantae 1768086

Showing of synonyms

  • Kayo MT, Simo MK, et al. (2021). Antifungal potential of extracts, fractions and compounds from Uvaria comperei (Annonaceae) and Oxyanthus unilocularis (Rubiaceae).. Natural product research,2021, 35(24), 5732-5736. [View] [PubMed]
Pubchem: 146156496

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(C(=O)C2)c3ccccc3

Level: 1

Mol. Weight: 300.31 g/mol

Structure

SMILES: C1C(=O)COc(c12)cccc2

Level: 0

Mol. Weight: 300.31 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 300.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.200
Plasma Protein Binding
60.12
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.300
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.420
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.950
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.960
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
3.880
Rat (Acute)
2.280
Rat (Chronic Oral)
1.920
Fathead Minnow
4.680
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
385.510
Hydration Free Energy
-7.860
Log(D) at pH=7.4
1.970
Log(P)
2.51
Log S
-3.6
Log(Vapor Pressure)
-6.89
Melting Point
129.04
pKa Acid
6.52
pKa Basic
2.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9744
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9716
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9617
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9566
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9487
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9487
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9384
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9286
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9283
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.9266
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9256
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.9200
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9197
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9192
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.9191
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.9170
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9170
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.9146
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.9143
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.9121
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.9086
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.9080
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9011
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8984
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8936
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8924
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8890
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8871
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8827
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8765
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8731
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8674
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8638
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8636
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8631
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8599
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8523
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8488
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8453
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.8392
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8335
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1 Q15750 TAB1_HUMAN Homo sapiens 3 0.8307
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8294
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8261
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8242
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8239
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8221
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8214
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8203
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8203
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8170
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8147
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8121
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8104
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.8066
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.8055
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8026
Flavonoid 3-O-glucosyltransferase A6XNC6 UGFGT_MEDTR Medicago truncatula 3 0.8024
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8020
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8001
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7941
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7928
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7902
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7898
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7894
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7883
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.7854
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7849
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7843
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7836
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7818
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7786
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7772
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7761
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7755
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7718
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7714
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7714
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7690
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7684
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7679
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7661
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7651
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7641
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7621
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7602
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7563
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7550
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7545
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7538
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7523
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7506
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7506
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7500
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7495
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7494
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7489
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7487
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7457
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7439
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7436
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7401
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7381
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7365
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7360
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 3 0.7359
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7358
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7322
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7313
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7302
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7277
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7277
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7274
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 3 0.7267
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7254
Isoflavone 4'-O-methyltransferase Q29U70 I4OMT_MEDTR Medicago truncatula 3 0.7247
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7245
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7229
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7202
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7190
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7189
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7184
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7182
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7171
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7169
Glycosyltransferase A4F1R4 A4F1R4_CLITE Clitoria ternatea 4 0.7165
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7165
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 3 0.7155
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7154
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.7151
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7147
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7143
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7140
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7140
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7138
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7135
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7113
Macrophage colony-stimulating factor 1 receptor P07333 CSF1R_HUMAN Homo sapiens 3 0.7111
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7095
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7093
Pyruvate kinase PKM P14618 KPYM_HUMAN Homo sapiens 3 0.7088
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7087
Quercetin 2,3-dioxygenase Q7SIC2 QDOI_ASPJA Aspergillus japonicus 3 0.7083
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7074
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7073
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7069
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7067
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7065
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7047
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7042
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7042
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7041
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7037
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7034
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7033
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7033
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7025
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7021
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7011
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7004

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