Hyperin - Compound Card

Hyperin

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Hyperin

Structure
Zoomed Structure
  • Family: Plantae - Rhamnaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21+/m1/s1
InChIKey OVSQVDMCBVZWGM-DTGCRPNFSA-N
Formula C21H20O12
HBA 12
HBD 8
MW 464.38
Rotatable Bonds 4
TPSA 210.51
LogP -0.54
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 464.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Viburnum tinus Adoxaceae Plantae 237959
2 Schinus molle Anacardiaceae Plantae 43851
3 Pistacia atlantica Anacardiaceae Plantae 434234
4 Asteriscus graveolens Asteraceae Plantae 73976
5 Arbutus unedo Ericaceae Plantae 84005
6 Euphorbia helioscopia Euphorbiaceae Plantae 154990
7 Hypericum humifusum Hypericaceae Plantae 626746
8 Crataegus sinaica Rosaceae Plantae 298646
9 Argania spinosa Sapotaceae Plantae 2945705
10 Cotula cinerea Asteraceae Plantae
11 Iphiona scabra Asteraceae Plantae 211591
12 Pallenis spinosa Asteraceae Plantae 73981
13 Polygonum senegalense Polygonaceae Plantae 471708
14 Acacia polyacantha Leguminosae/Fabaceae Plantae 875646
15 Ziziphus spina-christi Rhamnaceae Plantae 264981

Showing of synonyms

  • Shahat AA, Ismail SI, et al. (1998). Anti-HIV activity of flavonoids and proanthocyanidins from Crataegus sinaica. Phytomedicine,1998,5(2),133-136. [View] [PubMed]
  • Marzouk MS, Moharram FA, et al. (2006). Antioxidant flavonol glycosides from Schinus molle. Phytotherapy Research,2006,20(3),200-205. [View] [PubMed]
  • Ashu FA, Na-Iya J, et al. (2020). Antistaphylococcal Activity of Extracts, Fractions, and Compounds of Acacia polyacantha Wild (Fabaceae).. Evidence-based complementary and alternative medicine : eCAM,2020, 2020, 2654247. [View] [PubMed]
  • Rouis Z, Abid N, et al. (2013). Benzophenone glycosides from Hypericum humifusum ssp. austral. Journal of Natural Products,2013,76(5),979-982. [View] [PubMed]
  • Klika KD, Khallouki F, et al. (2015). Carboxy methyl and carboxy analogs argaminolics B and C. Records of Natural Products,2015,9(4),597-602. [View]
  • Shahat A.A, Pieters L, et al. (2001). Chemical and biological investigations on Zizyphus spina-christi L. Phytotherapy research : PTR, 2001, 15(7), 593-7. [View] [PubMed]
  • Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
  • Ahmed AA, Mabry TJ (1987). Flavonoids from Iphiona scabra. Phytochemistry,1987,26(5),1517-1518. [View]
  • Ahmed AA, Ishak MS, et al. (1991). Flavonoids of Asteriscus graveolens.. Journal of Natural Products,1991,54,4,1092-1093. [View]
  • Ahmed AA, el-Sayed NH, et al. (1987). Flavonoids of Cotula cinerea. Journal of Natural Products,1987,50(3),519-520. [View]
  • Ahmed AA, Spaller M, et al. (1992). Flavonoids of Pallenis spinosa (Asteraceae). Biochemical Systematics and Ecology,1992,20(8),785-786. [View]
  • Midiwo JO, Owino NO, et al. (1994). Flavonoids of Polygonum senegalense Part III: Isolation of dihydrochalcone glucoside and quercetin glycosides.. Bulletin of the Chemical Society of Ethiopia,1994,8(2),79-84. [View] [PubMed]
  • Mohamed MA, Marzouk MSA, et al. (2005). Phytochemical constituents and hepatoprotective activity of Viburnum tinus. Phytochemistry,2005,66,2780-2786. [View] [PubMed]
  • Legssyer A, Ziyyat A, et al. (2004). Tannins and catechin gallate mediate the vasorelaxant effect of Arbutus unedo on the rat isolated aorta. Phytotherapy Research,2004,18,889-894. [View] [PubMed]
  • Kawashty SA, Mosharrafa SAM, et al. (2000). The flavonoids of four Pistacia species in Egypt. Biochemical Systematics and Ecology,2000,28(9),915-917. [View] [PubMed]
Pubchem: 5281643
Kegg Ligand: C10073
Chebi: 67486
Nmrshiftdb2: 60021422
Metabolights: MTBLC67486
Pdb Ligand: J6O
Bindingdb: 429266
CPRiL: 56830
Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 464.38 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 464.38 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 464.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 464.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 464.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 464.38 g/mol

Antioxidant
Antistaphylococcal
Vasorelaxant

Absorption

Caco-2 (logPapp)
-6.26
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
2.15

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
81.16
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
13.210
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.610
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.140
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.920
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
-108.270
Rat (Acute)
2.420
Rat (Chronic Oral)
3.850
Fathead Minnow
3.820
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
647.560
Hydration Free Energy
-4.690
Log(D) at pH=7.4
-0.140
Log(P)
0.58
Log S
-4.22
Log(Vapor Pressure)
-11.81
Melting Point
210.01
pKa Acid
5.42
pKa Basic
8.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8943
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.8943
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8901
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8901
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8782
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8782
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8744
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8744
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8735
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8735
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8688
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8688
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8684
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8684
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8684
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8684
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8627
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8627
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8594
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8594
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8433
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8433
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8414
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8414
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8396
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8396
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8351
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8351
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8339
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8339
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8318
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8318
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8310
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8310
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8284
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8284
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8279
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8279
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8278
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8278
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8262
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8262
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8009
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8009
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7956
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7956
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7930
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7930
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7903
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7903
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7823
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7823
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7822
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7822
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7725
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7725
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7707
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7707
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7698
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7698
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7666
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7666
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7664
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7664
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7623
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7623
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7606
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7606
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7564
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7564
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7506
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7506
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7490
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7490
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7476
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7476
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7430
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7430
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7410
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7410
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7383
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7383
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7380
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7380
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7350
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7350
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7317
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7317
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7316
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7316
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7276
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7276
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7244
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7244
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7230
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7230
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.7227
Acetyl-CoA carboxylase 2 O00763 ACACB_HUMAN Homo sapiens 4 0.7227
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 4 0.7197
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 4 0.7197
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7188
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7188
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7148
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7148
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7139
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7139
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7134
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7134
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7121
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7121
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7115
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7115
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7109
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 6 0.7109
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7105
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7105
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7098
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7098
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7079
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.7079
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 5 0.7022
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 5 0.7022
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7014
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7014

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