3-(4-(glucopyranosyloxy)-5-hydroxy-2-methoxyphenyl)-7-hydroxy-4H-chromen-4-one - Compound Card

3-(4-(glucopyranosyloxy)-5-hydroxy-2-methoxyphenyl)-7-hydroxy-4H-chromen-4-one

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3-(4-(glucopyranosyloxy)-5-hydroxy-2-methoxyphenyl)-7-hydroxy-4H-chromen-4-one

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Isoflavone
Canonical Smiles OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1OOc1cc(OC)c(cc1O)c1coc2c(c1=O)ccc(c2)O)O)O
InChI InChI=1S/C22H22O12/c1-30-14-6-16(33-34-21-17(7-23)32-22(29)20(28)19(21)27)13(25)5-11(14)12-8-31-15-4-9(24)2-3-10(15)18(12)26/h2-6,8,17,19-25,27-29H,7H2,1H3/t17-,19-,20-,21-,22?/m1/s1
InChIKey ORJCRTQYNZMWPF-DYDAQHSGSA-N
Formula C22H22O12
HBA 12
HBD 6
MW 478.41
Rotatable Bonds 6
TPSA 188.51
LogP -0.01
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 478.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ononis angustissima Leguminosae/Fabaceae Plantae 672159

Showing of synonyms

  • Ghribi L, Waffo-Téguo P, et al. (2015). Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissimaL.. Bioorganic & medicinal chemistry letters, 2015, 25(18), 3825-30. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)occ(c2=O)-c3ccc(cc3)OOC4CCCOC4

Level: 2

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)-c3ccccc3

Level: 1

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1ccccc1OOC2CCCOC2

Level: 1

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.6
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.25
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.64

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.96
Plasma Protein Binding
73.9
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
Non-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
12.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.91
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.82
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.53
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
-209.71
Rat (Acute)
2.39
Rat (Chronic Oral)
3.8
Fathead Minnow
4.38
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
581.24
Hydration Free Energy
-3.45
Log(D) at pH=7.4
0.5
Log(P)
0.24
Log S
-4.11
Log(Vapor Pressure)
-11.4
Melting Point
192.62
pKa Acid
5.95
pKa Basic
5.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9255
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 4 0.9225
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9207
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9109
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9025
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8973
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8958
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8902
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8856
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8831
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8771
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8741
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8661
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8652
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8603
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8594
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8587
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 4 0.8515
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.8500
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8477
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8462
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8446
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8419
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8394
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 4 0.8359
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8327
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8290
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8236
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8229
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8208
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8196
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8123
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8115
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8068
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8004
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7987
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7976
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7968
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7946
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7933
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7851
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7831
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7826
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7788
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7691
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7655
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7655
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7639
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7630
Phenolphthiocerol/phthiocerol polyketide synthase subunit C P96202 PPSC_MYCTU Mycobacterium tuberculosis 3 0.7592
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 4 0.7567
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7556
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7530
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7529
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7482
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7444
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7419
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7418
Transthyretin P02766 TTHY_HUMAN Homo sapiens 4 0.7390
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7389
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7333
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7307
Bromodomain protein, putative Q8I240 Q8I240_PLAF7 Plasmodium falciparum 4 0.7300
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7299
Putative N-acetyl glucosaminyl transferase Q6U8B0 Q6U8B0_RAOTE Raoultella terrigena 3 0.7272
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7250
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7237
DNA polymerase theta O75417 DPOLQ_HUMAN Homo sapiens 4 0.7235
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7210
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7193
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7189
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7185
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7183
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 4 0.7162
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7162
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 3 0.7158
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7136
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7103
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7100
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7100
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7098
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7092
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7086
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7070
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7061
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 4 0.7021
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7018
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7007

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