2,4',6-trihydroxy-4-methoxybenzophenone-2-O-glucoside - Compound Card

2,4',6-trihydroxy-4-methoxybenzophenone-2-O-glucoside

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2,4',6-trihydroxy-4-methoxybenzophenone-2-O-glucoside

Structure
Zoomed Structure
  • Family: Plantae - Thymelaeaceae
  • Kingdom: Plantae
  • Class: Benzophenone
    • Subclass: Benzophenone Glycoside
Canonical Smiles OC[C@H]1OC(Oc2cc(OC)cc(c2C(=O)c2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C20H22O10/c1-28-11-6-12(23)15(16(24)9-2-4-10(22)5-3-9)13(7-11)29-20-19(27)18(26)17(25)14(8-21)30-20/h2-7,14,17-23,25-27H,8H2,1H3/t14-,17-,18+,19-,20?/m1/s1
InChIKey LCZPALDWQFYTCU-QJTRSWFLSA-N
Formula C20H22O10
HBA 10
HBD 6
MW 422.39
Rotatable Bonds 6
TPSA 166.14
LogP -0.48
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 422.12
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Gnidia involucrata Thymelaeaceae Plantae 142743

Showing of synonyms

  • Ferrari J, Terreaux C, et al. (2000). Benzophenone glycosides from Gnidia involucrata. Phytochemistry,2000,54(8),883-889. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)c2c(cccc2)OC3CCCCO3

Level: 2

Mol. Weight: 422.39 g/mol

Structure

SMILES: c1ccccc1C(=O)c2ccccc2

Level: 1

Mol. Weight: 422.39 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 422.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 422.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 422.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.34
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.92

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.79
Plasma Protein Binding
62.0
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
11.04
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.45
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.87
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.16
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
-22.48
Rat (Acute)
2.2
Rat (Chronic Oral)
4.01
Fathead Minnow
4.01
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
539.53
Hydration Free Energy
-10.1
Log(D) at pH=7.4
0.26
Log(P)
0.12
Log S
-3.78
Log(Vapor Pressure)
-10.39
Melting Point
165.36
pKa Acid
5.14
pKa Basic
4.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9324
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9324
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9155
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9155
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9098
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9098
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8844
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8844
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8838
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8838
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8776
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8776
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8654
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8654
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8436
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8436
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8424
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8424
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.8416
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.8416
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8119
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8119
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8084
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8084
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8063
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8063
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8004
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.8004
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7986
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7986
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7844
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.7844
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7792
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7792
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7774
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7774
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7649
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7649
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7556
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7556
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7549
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7549
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7544
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7544
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7523
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7523
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7477
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7477
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7410
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7410
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7365
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7365
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7318
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7318
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7288
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7288
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7280
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7280
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7277
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7277
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7256
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7256
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7252
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7252
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7248
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7248
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7209
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7209
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7207
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7207
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7184
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7184
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7152
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7152
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7130
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7130
F420H(2)-dependent reductase Rv1155 O06553 F420R_MYCTU Mycobacterium tuberculosis 3 0.7125
F420H(2)-dependent reductase Rv1155 O06553 F420R_MYCTU Mycobacterium tuberculosis 3 0.7125
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7105
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7105
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7067
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7067
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7058
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7058
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7057
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7057
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7047
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7047
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7037
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7037
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7030
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7030
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 4 0.7026
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 4 0.7026
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7021
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7021
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7020
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7020
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7018
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7018
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7016
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7016
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7008
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7008

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