1alpha-(beta-D-glucopyranoxy)-6alpha,7alpha-epoxy-4abeta,5alpha-dihydroxy-7-methyl-1,4a,5,6,7,7abeta-hexahydrocyclopenta[c]pyran - Compound Card

1alpha-(beta-D-glucopyranoxy)-6alpha,7alpha-epoxy-4abeta,5alpha-dihydroxy-7-methyl-1,4a,5,6,7,7abeta-hexahydrocyclopenta[c]pyran

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1alpha-(beta-D-glucopyranoxy)-6alpha,7alpha-epoxy-4abeta,5alpha-dihydroxy-7-methyl-1,4a,5,6,7,7abeta-hexahydrocyclopenta[c]pyran

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles OC[C@H]1O[C@@H](O[C@H]2OC=C[C@@]3([C@H]2[C@]2(C)O[C@@H]2[C@@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C15H22O10/c1-14-9-13(22-3-2-15(9,21)10(20)11(14)25-14)24-12-8(19)7(18)6(17)5(4-16)23-12/h2-3,5-13,16-21H,4H2,1H3/t5-,6-,7+,8-,9-,10+,11-,12+,13-,14+,15+/m1/s1
InChIKey UBAIOTDKPLIEDD-SANLAASLSA-N
Formula C15H22O10
HBA 10
HBD 6
MW 362.33
Rotatable Bonds 3
TPSA 161.6
LogP -3.45
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 362.12
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Teucrium polium Lamiaceae Plantae 1117157

Showing of synonyms

  • Elmasri W.A, Yang T, et al. (2015). Teucrium polium phenylethanol and iridoid glycoside characterization and flavonoid inhibition of biofilm-forming Staphylococcus aureus. Journal of natural products, 2015, 78(1), 2-9. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 362.33 g/mol

Structure

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 362.33 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 362.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.44
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.130
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.680
Plasma Protein Binding
32.96
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
6.250
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.470
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.140
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.230
Micronucleos
Safe
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
-7.020
Rat (Acute)
2.560
Rat (Chronic Oral)
3.340
Fathead Minnow
2.460
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
427.020
Hydration Free Energy
-16.240
Log(D) at pH=7.4
-2.080
Log(P)
-2.28
Log S
-0.83
Log(Vapor Pressure)
-14.25
Melting Point
124.91
pKa Acid
6.25
pKa Basic
2.99
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8266
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7852
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7247
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7074

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