Maesopsin 6-O-beta-D-glucopyranoside - Compound Card

Maesopsin 6-O-beta-D-glucopyranoside

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Maesopsin 6-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Iridaceae
  • Kingdom: Plantae
  • Class: Auronol Derivative
Canonical Smiles OCC1O[C@@H](Oc2cc3OC(C(=O)c3c(c2)O)(O)Cc2ccc(cc2)O)C([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H22O11/c22-8-14-16(25)17(26)18(27)20(31-14)30-11-5-12(24)15-13(6-11)32-21(29,19(15)28)7-9-1-3-10(23)4-2-9/h1-6,14,16-18,20,22-27,29H,7-8H2/t14?,16-,17+,18?,20-,21?/m1/s1
InChIKey MWYRZWOULAZZHR-RDBLRTHZSA-N
Formula C21H22O11
HBA 11
HBD 7
MW 450.4
Rotatable Bonds 5
TPSA 186.37
LogP -1.22
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 450.12
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Iris spuria Iridaceae Plantae 93026

Showing of synonyms

  • Farag SF, Kimura Y, et al. (2009). New isoflavone glycosides from Iris spuria L. (Calizona) cultivated in Egypt. Journal of Natural Medicines,2009,63(1),91-95. [View] [PubMed]
Pubchem: 42607792
Chebi: 179869
Nmrshiftdb2: 70031798

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(C2=O)Oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 450.4 g/mol

Structure

SMILES: O=C1COc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 450.4 g/mol

Structure

SMILES: c1ccccc1CC(C2=O)Oc(c23)cccc3

Level: 1

Mol. Weight: 450.4 g/mol

Structure

SMILES: O=C1COc(c12)cccc2

Level: 0

Mol. Weight: 450.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 450.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 450.4 g/mol

Antiviral

Absorption

Caco-2 (logPapp)
-6.73
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.53
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
51.09
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
10.45
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.24
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.76
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.25
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
-73.94
Rat (Acute)
2.4
Rat (Chronic Oral)
4.11
Fathead Minnow
4.11
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
559.67
Hydration Free Energy
-4.34
Log(D) at pH=7.4
-0.15
Log(P)
-0.82
Log S
-3.28
Log(Vapor Pressure)
-11.52
Melting Point
192.51
pKa Acid
4.6
pKa Basic
6.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9148
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9148
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9076
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9076
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8935
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8935
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8794
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8794
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8691
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8691
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8601
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8601
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8354
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8354
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8353
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8353
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8221
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8221
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 5 0.8103
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 5 0.8103
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8097
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8097
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8096
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8096
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8065
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8065
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8046
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8046
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8036
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8036
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 4 0.7999
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 4 0.7999
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7940
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7940
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7906
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7906
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7872
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7872
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7749
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7749
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7739
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7739
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7731
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7731
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7637
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7637
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7559
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7559
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7547
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7547
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7523
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7523
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7477
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7477
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7407
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7407
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7368
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7368
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7357
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7357
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7331
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7331
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7320
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7320
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7285
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7285
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7265
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7265
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7264
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7264
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7215
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7215
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7173
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7173
Polymerase basic protein 2 Q2LG68 Q2LG68_9INFA Influenza A virus) 4 0.7148
Polymerase basic protein 2 Q2LG68 Q2LG68_9INFA Influenza A virus) 4 0.7148
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7146
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7146
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7143
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7143
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7142
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7142
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7101
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7101
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7094
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7094
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7083
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7083
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7071
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7071
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7070
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7070
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7069
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7069
Cytosolic heat shock protein 90 Q7XJ80 Q7XJ80_HORVU Hordeum vulgare 3 0.7068
Cytosolic heat shock protein 90 Q7XJ80 Q7XJ80_HORVU Hordeum vulgare 3 0.7068
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7065
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7065
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7025
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7025
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7024
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7024
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7008
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7008

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