(5R,6R,Z)-5,6-dihydroxy-5,6-dihydro-2H-thiopyran-2-one O-methyl oxime beta-D-glucopyranoside - Compound Card

(5R,6R,Z)-5,6-dihydroxy-5,6-dihydro-2H-thiopyran-2-one O-methyl oxime beta-D-glucopyranoside

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(5R,6R,Z)-5,6-dihydroxy-5,6-dihydro-2H-thiopyran-2-one O-methyl oxime beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Rubiaceae
  • Kingdom: Plantae
  • Class: Oxime
Canonical Smiles OC[C@H]1O[C@@H](O[C@@H]2S/C(=N\OC)/C=C[C@H]2O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C12H19NO8S/c1-19-13-7-3-2-5(15)12(22-7)21-11-10(18)9(17)8(16)6(4-14)20-11/h2-3,5-6,8-12,14-18H,4H2,1H3/b13-7-/t5-,6-,8-,9+,10-,11+,12-/m1/s1
InChIKey ACTUTXLTEUKWIN-WLHCVJQASA-N
Formula C12H19NO8S
HBA 10
HBD 5
MW 337.35
Rotatable Bonds 4
TPSA 141.2
LogP -2.25
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 337.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ixora undulata Rubiaceae Plantae 1231253

Showing of synonyms

  • Sugimoto S, Wanas AS, et al. (2014). Structure elucidation of secondary metabolites isolated from the leaves of Ixora undulate and their inhibitory activity toward advanced glycation end-products formation. Phytochemistry,2014,108,189-195. [View] [PubMed]
Pubchem: 102341727
Nmrshiftdb2: 70038283

No compound-protein relationship available.

Structure

SMILES: N=C1C=CCC(S1)OC2CCCCO2

Level: 1

Mol. Weight: 213.3 g/mol

Structure

SMILES: N=C1C=CCCS1

Level: 0

Mol. Weight: 113.19 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.22
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.640
Plasma Protein Binding
42.17
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
2.370
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.080
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.680
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.980
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
-3.420
Rat (Acute)
2.240
Rat (Chronic Oral)
2.790
Fathead Minnow
3.070
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
442.970
Hydration Free Energy
-20.620
Log(D) at pH=7.4
-0.310
Log(P)
-1.56
Log S
-0.95
Log(Vapor Pressure)
-13.04
Melting Point
142.94
pKa Acid
8.0
pKa Basic
3.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8198
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8198
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7861
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7861
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7682
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7682

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