1alpha-hydroxy-8alpha,13-diacetoxy-germacra-4,7(11),9-trien-6alpha,12-olide - Compound Card

1alpha-hydroxy-8alpha,13-diacetoxy-germacra-4,7(11),9-trien-6alpha,12-olide

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1alpha-hydroxy-8alpha,13-diacetoxy-germacra-4,7(11),9-trien-6alpha,12-olide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Lactone
Canonical Smiles CC(=O)O[C@H]1C[C@@]2(C)[C@H](O)CCC(=C)[C@@H]2[C@@H]2C1=C(COC(=O)C)C(=O)O2
InChI InChI=1S/C19H24O7/c1-9-5-6-14(22)19(4)7-13(25-11(3)21)15-12(8-24-10(2)20)18(23)26-17(15)16(9)19/h13-14,16-17,22H,1,5-8H2,2-4H3/t13-,14+,16+,17-,19-/m0/s1
InChIKey FTPSTBSYEVZNTA-RIFUYLIYSA-N
Formula C19H24O7
HBA 7
HBD 1
MW 364.39
Rotatable Bonds 3
TPSA 99.13
LogP 1.44
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.63
Exact Mass 364.15
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: 14137561
Nmrshiftdb2: 70018555

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 364.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.55
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.32
Plasma Protein Binding
45.54
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.22
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.01
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.99
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
-3.45
Rat (Acute)
3.47
Rat (Chronic Oral)
1.95
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
374.51
Hydration Free Energy
-7.46
Log(D) at pH=7.4
1.02
Log(P)
1.26
Log S
-3.02
Log(Vapor Pressure)
-7.38
Melting Point
159.32
pKa Acid
8.0
pKa Basic
3.79
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 0.9532
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9532
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7355
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7355

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