1'''-O-beta-D-glucosylformoside - Compound Card

1'''-O-beta-D-glucosylformoside

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1'''-O-beta-D-glucosylformoside

Structure
Zoomed Structure
  • Family: Plantae - Oleaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Secoiridoid Glucoside
Canonical Smiles OC[C@H]1OC(OCCc2ccc(cc2)OC(=O)C[C@H]2/C(=C\C)/[C@@H](CC=C2C(=O)OC)OC2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C32H44O16/c1-3-17-19(18(30(42)43-2)8-9-20(17)46-32-29(41)27(39)25(37)22(14-34)48-32)12-23(35)45-16-6-4-15(5-7-16)10-11-44-31-28(40)26(38)24(36)21(13-33)47-31/h3-8,19-22,24-29,31-34,36-41H,9-14H2,1-2H3/b17-3+/t19-,20+,21+,22+,24+,25+,26-,27-,28+,29+,31?,32?/m0/s1
InChIKey JYDIJMBUETWWMG-XVMDAHJBSA-N
Formula C32H44O16
HBA 16
HBD 8
MW 684.69
Rotatable Bonds 12
TPSA 251.36
LogP -2.41
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 48
Formal Charge 0
Fraction CSP3 0.62
Exact Mass 684.26
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Fraxinus excelsior Oleaceae Plantae 38873
2 Fraxinus excelsior Oleaceae Plantae 38873
3 Fraxinus angustifolia Oleaceae Plantae 166594

Showing of synonyms

  • Ibarra A, Bai N, et al. (2011). Fraxinus excelsior seed extract FraxiPureTM limits weight gains and hyperglycemia in high-fat diet-induced obese mice. Phytomedicine,2011,18(6),479-485. [View]
  • Bai N, He K, et al. (2010). Iridoids from Fraxinus excelsior with adipocyte differentiation-inhibitory and PPARalpha activation activity. Journal of Natural Products,2010,73(1),2-6. [View] [PubMed]
  • García-Villalba R, Tomás-Barberán FA, et al. (2015). Targeted and untargeted metabolomics to explore the bioavailability of the secoiridoids from a seed/fruit extract (Fraxinus angustifolia Vahl) in human healthy volunteers: a preliminary study. Molecules,2015,20(12),22202-22219. [View] [PubMed]
Pubchem: 163067737

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC2CC=CC(C2=C)CC(=O)Oc(cc3)ccc3CCOC4CCCCO4

Level: 3

Mol. Weight: 684.69 g/mol

Structure

SMILES: C1CC=CC(C1=C)CC(=O)Oc(cc2)ccc2CCOC3CCCCO3

Level: 2

Mol. Weight: 684.69 g/mol

Structure

SMILES: c1ccccc1OC(=O)CC(C2=C)C=CCC2OC3CCCCO3

Level: 2

Mol. Weight: 684.69 g/mol

Structure

SMILES: C1CC=CC(C1=C)CC(=O)Oc2ccccc2

Level: 1

Mol. Weight: 684.69 g/mol

Structure

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 684.69 g/mol

Structure

SMILES: C1C=CCC(C1=C)OC2CCCCO2

Level: 1

Mol. Weight: 684.69 g/mol

Structure

SMILES: C=C1CC=CCC1

Level: 0

Mol. Weight: 684.69 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 684.69 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 684.69 g/mol

Adipocyte differentiation-inhibitory
Antiobesity property

Absorption

Caco-2 (logPapp)
-6.42
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
78.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
72.63
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
3.34
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.97
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.75
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.0
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
-145154.1
Rat (Acute)
2.84
Rat (Chronic Oral)
4.52
Fathead Minnow
198.3
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
10783.17
Hydration Free Energy
-2.92
Log(D) at pH=7.4
0.7
Log(P)
-1.21
Log S
-2.38
Log(Vapor Pressure)
-352.81
Melting Point
181.38
pKa Acid
4.06
pKa Basic
4.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.9439
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.9439
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8900
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8900
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8735
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.8735
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8716
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8716
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8317
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8317
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8219
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8219
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8186
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8186
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7923
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7923
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7860
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7860
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7539
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7539
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7385
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7385
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7246
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7246
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7229
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7229
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7178
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7178
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7032
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7032

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