5-O-beta-glucopyranosylcarvotacetone - Compound Card

5-O-beta-glucopyranosylcarvotacetone

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5-O-beta-glucopyranosylcarvotacetone

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Carvotacetone Derivative
Canonical Smiles OC[C@H]1OC(O[C@H]2C(CC=C(C2=O)CO)C(C)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C16H26O8/c1-7(2)9-4-3-8(5-17)11(19)15(9)24-16-14(22)13(21)12(20)10(6-18)23-16/h3,7,9-10,12-18,20-22H,4-6H2,1-2H3/t9?,10-,12-,13+,14-,15+,16?/m1/s1
InChIKey ACRZTZHEHYXBPA-SJDAFVTOSA-N
Formula C16H26O8
HBA 8
HBD 5
MW 346.38
Rotatable Bonds 5
TPSA 136.68
LogP -1.66
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 346.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sphaeranthus bullatus Asteraceae Plantae 1548657

Showing of synonyms

  • Machumi F, Yenesew A, et al. (2012). Antiparasitic and anticancer carvotacetone derivatives of Sphaeranthus bullatus. Natural Product Communications,2012,7(9),1123-1126. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCCC1OC2CCCCO2

Level: 1

Mol. Weight: 346.38 g/mol

Structure

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 346.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 346.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
46.36
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
3.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.35
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.26
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.48
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
-2.95
Rat (Acute)
2.06
Rat (Chronic Oral)
3.18
Fathead Minnow
2.57
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
440.72
Hydration Free Energy
-19.22
Log(D) at pH=7.4
0.44
Log(P)
-0.94
Log S
-1.09
Log(Vapor Pressure)
-11.84
Melting Point
149.03
pKa Acid
6.19
pKa Basic
6.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7717
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7717
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7543
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7543
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7503
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7503
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7472
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 4 0.7472
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7462
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7462
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7164
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7164

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