Phloretin 3′,5′-di-C-beta-D-glucoside - Compound Card

Phloretin 3′,5′-di-C-beta-D-glucoside

Select a section from the left sidebar

Phloretin 3′,5′-di-C-beta-D-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Chalcone
    • Subclass: Dihydrochalcone
Canonical Smiles OC[C@@H]1O[C@H]([C@H]([C@@H]([C@H]1O)O)O)c1c(O)c(C(=O)CCc2ccc(cc2)O)c(c(c1O)[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O
InChI InChI=1S/C27H34O15/c28-7-12-17(32)22(37)24(39)26(41-12)15-19(34)14(11(31)6-3-9-1-4-10(30)5-2-9)20(35)16(21(15)36)27-25(40)23(38)18(33)13(8-29)42-27/h1-2,4-5,12-13,17-18,22-30,32-40H,3,6-8H2/t12-,13+,17-,18+,22+,23-,24-,25+,26-,27+
InChIKey WAWHTTXPRUWFCZ-IFUVDCKGSA-N
Formula C27H34O15
HBA 15
HBD 12
MW 598.55
Rotatable Bonds 8
TPSA 278.29
LogP -2.65
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 598.19
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Galium brunneum Rubiaceae Plantae 25168

Showing of synonyms

  • Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CCC(=O)c2cc(C3CCCCO3)cc(c2)C4CCCCO4

Level: 3

Mol. Weight: 598.55 g/mol

Structure

SMILES: c1ccccc1CCC(=O)c2cc(ccc2)C3CCCCO3

Level: 2

Mol. Weight: 598.55 g/mol

Structure

SMILES: O1CCCCC1c2cc(ccc2)C3CCCCO3

Level: 2

Mol. Weight: 598.55 g/mol

Structure

SMILES: c1ccccc1C(=O)CCc2ccccc2

Level: 1

Mol. Weight: 598.55 g/mol

Structure

SMILES: c1ccccc1C2CCCCO2

Level: 1

Mol. Weight: 598.55 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 598.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 598.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.49
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-6.650
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
7.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.430
Plasma Protein Binding
56.89
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
5.910
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.980
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.580
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.230
Micronucleos
Toxic
NR-AhR
Safe
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
-6865.770
Rat (Acute)
2.290
Rat (Chronic Oral)
4.440
Fathead Minnow
11.400
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
650.810
Hydration Free Energy
-2.930
Log(D) at pH=7.4
-1.840
Log(P)
-0.36
Log S
-2.68
Log(Vapor Pressure)
-14.38
Melting Point
164.17
pKa Acid
0.71
pKa Basic
12.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9277
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.9207
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9103
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.8888
Thiazole tautomerase P25053 TENI_BACSU Bacillus subtilis 3 0.8850
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8789
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8695
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8616
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8347
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8294
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.8253
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.8147
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8128
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8114
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7986
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7842
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7838
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7811
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7802
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7766
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7755
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7688
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7628
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7606
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7586
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7506
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7399
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7392
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7328
Ethylene receptor 1 P49333 ETR1_ARATH Arabidopsis thaliana 3 0.7324
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.7319
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7294
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7284
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7247
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7245
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7245
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7213
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7183
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7174
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7157
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7143
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7137
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7132
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7121
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7111
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.7093
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7084
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7082
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7067
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7057
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7040
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7038
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7012
23S rRNA (guanine(745)-N(1))-methyltransferase P36999 RLMA_ECOLI Escherichia coli 3 0.7006
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7006

Download SDF