(-)-puerol B-2'-O-beta-D-glucopyranose - Compound Card

(-)-puerol B-2'-O-beta-D-glucopyranose

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(-)-puerol B-2'-O-beta-D-glucopyranose

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Pueroside
    • Subclass: Pueroside Glycoside
Canonical Smiles OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O)OOc1cc(OC)ccc1C1=CC(=O)OC1Cc1ccc(cc1)O
InChI InChI=1S/C24H26O11/c1-31-14-6-7-15(16-10-20(27)32-17(16)8-12-2-4-13(26)5-3-12)18(9-14)34-35-23-22(29)21(28)19(11-25)33-24(23)30/h2-7,9-10,17,19,21-26,28-30H,8,11H2,1H3/t17?,19-,21-,22+,23-,24?/m1/s1
InChIKey JWOVVTLYVBZYGU-RJGJMOQZSA-N
Formula C24H26O11
HBA 11
HBD 5
MW 490.46
Rotatable Bonds 8
TPSA 164.37
LogP 0.06
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 490.15
Number of Lipinski Rule Violations 1
# 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: c1ccccc1CC2OC(=O)C=C2c3c(cccc3)OOC4CCCOC4

Level: 3

Mol. Weight: 490.46 g/mol

Structure

SMILES: C1OC(=O)C=C1c2c(cccc2)OOC3CCCOC3

Level: 2

Mol. Weight: 490.46 g/mol

Structure

SMILES: c1ccccc1CC2OC(=O)C=C2c3ccccc3

Level: 2

Mol. Weight: 490.46 g/mol

Structure

SMILES: c1ccccc1OOC2CCCOC2

Level: 1

Mol. Weight: 490.46 g/mol

Structure

SMILES: O=C1C=CC(O1)Cc2ccccc2

Level: 1

Mol. Weight: 490.46 g/mol

Structure

SMILES: C1OC(=O)C=C1c2ccccc2

Level: 1

Mol. Weight: 490.46 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 490.46 g/mol

Structure

SMILES: O=C1C=CCO1

Level: 0

Mol. Weight: 490.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 490.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.94
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.0
Plasma Protein Binding
54.43
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.46
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.78
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.62
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.29
Micronucleos
Toxic
NR-AhR
Safe
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
-431.17
Rat (Acute)
2.4
Rat (Chronic Oral)
3.51
Fathead Minnow
4.35
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
539.57
Hydration Free Energy
-2.98
Log(D) at pH=7.4
1.02
Log(P)
-0.73
Log S
-3.29
Log(Vapor Pressure)
-10.97
Melting Point
183.36
pKa Acid
6.1
pKa Basic
3.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8909
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8906
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8794
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8676
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8473
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8418
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8402
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8351
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8299
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8284
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8219
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8117
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8038
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8009
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7954
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7771
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7764
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7645
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7558
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7557
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7547
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7466
Nucleoside diphosphate kinase P15266 NDK_MYXXA Myxococcus xanthus 3 0.7450
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7447
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7444
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7438
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7431
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7418
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7415
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7399
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7398
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7380
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7364
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7357
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7356
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7353
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7303
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7294
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7289
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7242
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7234
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7199
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7162
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7141
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7106
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7091
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7080
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7077
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7047
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7029
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7027
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7024
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7011
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7006

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