8alpha,13-diacetoxy-1beta-hydroxyeudesma-4(15),7(13)-dien-6a,12-olide - Compound Card

8alpha,13-diacetoxy-1beta-hydroxyeudesma-4(15),7(13)-dien-6a,12-olide

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8alpha,13-diacetoxy-1beta-hydroxyeudesma-4(15),7(13)-dien-6a,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)OCC1=C2[C@@H](O)C[C@@]3([C@@H]([C@H]2OC1=O)C(=C)CC[C@H]3O)C
InChI InChI=1S/C17H22O6/c1-8-4-5-12(20)17(3)6-11(19)13-10(7-22-9(2)18)16(21)23-15(13)14(8)17/h11-12,14-15,19-20H,1,4-7H2,2-3H3/t11-,12+,14+,15-,17-/m0/s1
InChIKey JFZHPKCGMPFGFG-FDCPPYJTSA-N
Formula C17H22O6
HBA 6
HBD 2
MW 322.36
Rotatable Bonds 2
TPSA 93.06
LogP 0.87
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 322.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Brocchia cinerea Asteraceae Plantae 282208

Showing of synonyms

  • Jakupovic J, Aal MA, et al. (1988). Further glaucolides and other sesquiterpene lactones from Brocchia cinerea.. Phytochemistry,1988,27(7),2219-2224. [View]
Pubchem: 14137559
Nmrshiftdb2: 70018561

No compound-protein relationship available.

Structure

SMILES: C=C1CCCC(CC2)C1C(C2=3)OC(=O)C3

Level: 0

Mol. Weight: 322.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.38
Plasma Protein Binding
39.33
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
8.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.53
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.34
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.71
Rat (Acute)
3.76
Rat (Chronic Oral)
2.01
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
367.44
Hydration Free Energy
-9.35
Log(D) at pH=7.4
0.39
Log(P)
1.01
Log S
-2.2
Log(Vapor Pressure)
-7.3
Melting Point
157.62
pKa Acid
7.2
pKa Basic
3.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9576
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9576
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8815
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8815
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7302
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7302

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