1beta,10alpha,4alpha,5beta-diepoxy-8alpha hydroxy-glechoman-8alpha,12-olide - Compound Card

1beta,10alpha,4alpha,5beta-diepoxy-8alpha hydroxy-glechoman-8alpha,12-olide

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1beta,10alpha,4alpha,5beta-diepoxy-8alpha hydroxy-glechoman-8alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles O=C1O[C@@]2(C(=C1C)CC1O[C@]1(C)CCC1[C@@](C2)(C)O1)O
InChI InChI=1S/C15H20O5/c1-8-9-6-11-13(2,19-11)5-4-10-14(3,18-10)7-15(9,17)20-12(8)16/h10-11,17H,4-7H2,1-3H3/t10?,11?,13-,14+,15+/m1/s1
InChIKey HHGREWJPFBZWTH-UFUHOSPJSA-N
Formula C15H20O5
HBA 5
HBD 1
MW 280.32
Rotatable Bonds 0
TPSA 71.59
LogP 1.44
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 280.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Smyrnium olusatrum Apiaceae Plantae 40962

Showing of synonyms

  • El-Gamal AA (2001). Sesquiterpene lactones from Smyrnium olusatrum. Phytochemistry,2001,57(8),1197-1200. [View]
Pubchem: 162887373

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC3C(O3)CC4C(C1)=CC(=O)O4

Level: 0

Mol. Weight: 280.32 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.13

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.08
Plasma Protein Binding
11.95
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.78
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.31
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.08
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
-2.76
Rat (Acute)
2.76
Rat (Chronic Oral)
1.22
Fathead Minnow
3.78
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
334.42
Hydration Free Energy
-6.47
Log(D) at pH=7.4
0.93
Log(P)
1.21
Log S
-1.62
Log(Vapor Pressure)
-4.85
Melting Point
81.15
pKa Acid
4.61
pKa Basic
1.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8380
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8380
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7706
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7706

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